100 Years, 50 Losers: #1

“It’s a Festivus Miracle!”

George Costanza, Seinfeld

Played By: Jason Alexander

Born to Lose: I was watching some NFL TV special on the Top Ten Power Running Backs of All-Time, and some guy that when it came to the subject of power running backs, “Jim Brown is #1. And there is no #2.” The same could very, very easily be applied to the case of George Constanza when it comes to TV losers. Sure, there are some great loser characters out there–the great majority of which have been listed on this blog in the last month or so–but they are all nothing compared to George. Mark Corrigan? Amateur. Coach McGuirk? Wannabe. Brian Krakow? Call me in 20 years, kid. In fact, half of the characters on this list wouldn’t even exist if not for the trails that George has blazed for TV loserdom over his eight or so years of existence. Ranking George among the loser TV characters in history is like comparing Orson Welles movies, current Lakers starters, or Gin Blossoms singles–each category has a bunch of quality contenders, but there’s only one Citizen Kane/Kobe Bryant/”Hey Jealousy”. (And please spare me your e-mails, you Lady from Shanghai / Andrew Bynum / “Allison Road” apologists).

Such a classic character is Costanza–not only a slam dunk for the best loser character in TV history, but almost inarguably the best character period in TV history–that I’m not gonna waste precious webspace trying to explain or justify his greatness. Instead, I have prepared a countdown of the Top 50 Moments in George Costanza history–each of which individually can go head-to-head with any of the best moments from any of the 49 other entries on this list. Gotta find your own YouTubes, though–as if you don’t have all these memorized already…

(Happy Holidays, everyone)

50. George argues about death with Kramer, who swears he’s not bothered by it. “See, now that bothers me even more than dying bothers me–cause it’s people like you who live to be a hundred and twenty because you’re not bothered by it!!” (The Parking Garage)

49. George attempts to get a frequent flyer mile discount for visiting his girlfriend’s dead relative. He pisses off the family too much for them to sign off on the death, so instead he just takes a picture of himself by the casket. (The Implant)

48. George feuds with a similarly portly, obsessive man about a nice suit going on sale. The two compete for who will get it to it first once it goes on sale, but George hedges his bets by hiding it in a different rack the night before.  (The Pie)

47. George buys Elaine a Big Salad, but is miffed when his girlfriend is the one who hands it to her, refusing to acknowledge him as the source. He can’t resist but tell her that he deserves the credit, and his girlfriend eventually breaks up with him for it. (The Big Salad)

46. George explicitly hires an unattractive secretary so she won’t distract him, but ends up being impressed enough with her efficiency that he sleeps with her anyway. In the heat of passion, he shouts out “I’M GIVING YOU  A RAISE!!!” (The Secretary)

45. George gets upset by Jerry’s refusal to be excited about his relationship with Susan’s friend, thereby eliminating the chance of the four of them spending all their time together. “I thought we were going to be like the Gatsbys!!” he exclaims, to the comprehension of no one. (The Friars Club)

44. George tries to get fired by the Yankees so he can be hired by the Mets, but his attempts to do so all backfire, as when he streaks on the field in the middle of the game, but still wears a body suit out of shyness, getting himself affectionately drubbed “Body Suit Man” by the general public. (The Millennium)

43. George tries to get a picture incriminating him as the guy that once threw his boss’s stereo into the ocean altered so that he’s not in the picture, but instead the photo guy takes out his boss. “You lost a lot of hair,” he informs George. “I AM AWARE!!!!” he responds. (The Slicer)

42. Shrinkage. (The Hamptons)

41. George points out to a woman that her husband never says God Bless You to her, leading her to fall out of love with her husband and start crushing on him. “An affair,” George contemplates. “It’s so adult!” (The Good Samaritan) 

40. “We had a pact!” (Only true losers keep a trump card like this in the back of their brain at all times, just in case). (Recurring)

39. George decides that his nickname heretofore will be T-Bone, and orders t-bones at the office all the time in the hopes of acquiring the nickname among his co-workers semi-organically. However, it is instead given to another worker, causing George to try to pressure him into giving it to him. “OK, OK, you can have T-Bone…just stop crying.” “I’m not crying!” (The Maid)

38. George tries an ice breaking trick that worked on Elaine–touching the fabric a woman is wearing and asking her what it is–and learns that different seduction techniques work for different people. (The Sniffing Accountant)

37. George is disparaged by his friends for pissing in the shower at the gym. “IT’S ALL PIPES!!!” he protests. (The Wife)

36. George neglects to get the details on a big project he thinks he’s supposed to do, but gets clued in that he’s “got to go downtown…just like the song.” He and Jerry analyze the lyrics of “Downtown,” line-by-line, until George concludes, “I got nothing.” (The Bottle Deposit, Pt. 1)

35. George is unmoved by Jerry’s repeated apologies for sleeping with his friend (and George’s potential new squeeze) Nina, remarking “You can stuff your sorries IN A SACK, mister!!” to the comprehension of no one. (The Betrayal)

34. George attempts to reclaim some dignity against a bad date that ruined his sweater and abandoned him years ago by confronting her at her baby shower, wearing the same sweater. He ends up helping her carry her stuff out of the apartment instead. (The Baby Shower)

33. George, having told his unemployment officer that he’s working as a latex salesman at the imaginary Vanderlay Industries (under Jerry’s phone number), hears Kramer telling the officer that he has the wrong number, and comes crashing out of the bathroom with his pants around his ankles, to no avail. “And you want to be my latex salesman…” Jerry gloats. (The Boyfriend, Pt. 2)

32. George is caught eating a bitten eclair out of his girlfriend’s mother’s trash can. Jerry summarizes the situation: “You find yourself in the kitchen, you see an eclair in the receptacle, and you think to yourself: What the hell, I’ll just eat some trash?” (The Soup)

31. George is incensed by a girl breaking up with him using “It’s not you, it’s me,” since George claims to have “INVENTED ‘IT’S NOT YOU IT’S ME’!!” After must badgering, the girl breaks down–“All right, George…it’s you.” “YOU’RE DAMN RIGHT IT’S ME!” he exclaims. (The Lip Reader)

30. George, through a variety of circumstances, convinces his office supervisors that he is disabled, and eventually gets a motorized scooter for his efforts. “Well, it’s nice to know that you’ll be going to hell at no more than three miles per hour,” Jerry remarks. (The Butter Shave)

29. George thinks he’s come up with the ultimate movie commentary track when his exclamation of “THAT’S GOTTA HURT!” draws laughter during the climax of Blimp: The Hindenburg Story. His second time through, he is upstaged by a guy with a laser pointer. (The Puerto Rican Day)

28. George notices that he tends to hurt himself by trying to be funny for too long after making one good joke, so after making his co-workers crack up at a staff meeting, he says “Thanks, folks, you’ve been great!” and makes his exit. Consequently, George’s boss kicks everyone else on the staff off a project but him, explaining “They were BO-RING!” (The Burning)

27. George ruins his and Jerry’s pitch meeting at NBC, claiming that their not being receptive to his idea of a “Show About Nothing” is disrupting his artistic integrity. Later at the diner, a seething Jerry fumes at George: “You’re NOT artistic, and you HAVE NO INTEGRITY!!” (The Pitch)

26. George is told by a mutual friend of his and Jerry’s that he faked having cancer. Despite being sworn to secrecy, Jerry sees through George’s infamously terrible “poker face” immediately, and determines that he, in fact, be holding “A FULL HOUSE??!?!?!” (The Scofflaw)

25. George, dating a girl who claims that looks aren’t important to her, gets to act out his much-ballyhooed fantasy: Ensconcing himself in velvet, showing up to the diner head-to-toe in the substance. (The Doodle)

24. George, being denied sex by his sick girlfriend, finally starts to think clearly, and discovers that he has untapped reservoirs of brilliance when his mind is not flooded by thoughts of sex. Despite this, he ends up ruining his brain hours before he’s supposed to give a speech at his and Jerry’s old middle school by having sex with a Portugese waitress. “I calculated my odds of ever getting together with a Portugese waitress,” he explains to Jerry. “Mathematically, I had to do it.” (The Abstinence)

23. George’s imaginary Christmas charity fund–The Human Fund: Money For People. (The Strike)

22. George creates a candy bar police lineup to try to ensnare a mechanic who he believes stole his Twix bar. “THEY WERE ALL TWIX!!” he breaks down after the ruse is ruined. (The Dealership)

21. George, able to live off his severance package from the Yankees for a few months, declares it the “Summer of George!” and decides to spend three months watching TV and eating out of his chair-refridgerator. (Side note: Whenever I spent an unemployed summer in college, Victor would pull out the same old “oh, so it’s going to be the Summer of Utz, huh?” chestnut) (Tbe Summer of George)

20. George, having made the rash decision to quit his job over a bathroom-related injustice, breaks down his job prospects with Jerry.

“Maybe I could be like, a [baseball] announcer. Like a color man. You know how I always make those interesting comments during the game?”
“Yeah, Yeah. You make good comments.”
“What about that?”
“Well, they tend to give those jobs to ex-ballplayers, and people that are, you know…in broadcasting.”
“…well that’s really not fair.” (The Revenge)

19. George’s man-crush on Elaine’s extreme-sports beau comes to a tragic end when he accidentally causes Tony a nasty, face-destroying spill while rock climbing. “STEP OFF, GEORGE!!!” (The Stall)

18. George advises Jerry on how to pass a lie-detector test with his cop girlfriend about whether or not he watches Melrose Place. “Remember–it’s not a lie if you believe it.” (The Beard)

17. George’s answering machine message, to the tune of the “Greatest American Hero” theme.

“Believe it or not / George isn’t at home / Please leave a messaaaaage / At the beep / I must be out / Or I’d pick up the phone / Wheeeeere could I beeeeeee? / Beleieve it or not / I’m not hooooome!!!!”

The little dance he does while he sings along with it seals the deal. (The Susie)

16. George, trying to get out of a relationship with a woman who won’t let him break up with her, cheats on her with a woman who refuses to have sex with him. He tries to get them to “discover” each other, but neither is moved enough by his betrayal to allow him to end their respective relationships. “All right…” he resigns himself, repeatedly. (The Strong Box)

15. George is furious when Jerry tells him, off the cuff, that he slept with Elaine the previous night, and then claims he’s “not in the mood” to give details. George offers the following: “You ask me to have lunch, tell me you slept with Elaine, and then say you’re not in the mood for details. Now you listen to me. I want details and I want them right now. I don’t have a job, I have no place to go. You’re not in the mood? WELL YOU GET IN THE MOOD!!!!” (The Deal)

14. George achieves his dream existence as a highly-paid, under-worked, over-pursued hand model, but it all comes crashing down when the low-talker pushes him into a scalding hot iron. So close… (The Puffy Shirt)

13. George discovers that he’s better off in life doing the exact opposite of what he would normally do, resulting in him taking it easy while driving, standing up to some punks at the movie theater, telling a woman he just met that he’s unemployed and lives with his parents, and insulting George Steinbrenner during an interview with the Yankees. Evidently, he unlearns this lesson during the Seinfeld off-season and is back to his charmless self by the next premiere. (The Opposite)

12. George gets pitched by Kramer to move to LA, analyzing how pathetic George’s life in New York is. “Do you have any conceivable reason to get up in the morning?” Kramer ultimately poses to him. “I like to get the Daily News,” George meekly responds.

11. George’s dream name for his son-or-daughter-to-be, Seven, is hijacked by Susan’s friends, who are actually expecting a baby. This deeply disturbs George, who berates the woman for being selfish on her way to the delivery room and ultimately pleads with them “PLEASE!! I HAVE SO LITTLE!!!” (The Seven) 

10. George gets the benefit of Elaine’s misconception that it was his presence, and not her dancing, that turned her entire office against her at their most recent party, by making himself seem like a bad boy to Elaine’s cute underling Anna. This is eventually undercut somewhat by her discovery of the orthopedic back pillow and FiberCon he keeps in his car, and ultimately completely undone when he cries after getting arrested for bootlegging. “Why did the policeman have to yell at me like that?” he bemoans. (The Little Kicks)

9. George gives the gruesome details of his life story to the approval board of an apartment he wants to move into, so he can out-maudlin the survivor of the Andrea Dorea wreck that he’s competing with. His summation: “In closing, these stories have not been embellished, because…they need no embellishment. They are simply, horrifyingly, the story of my life as a short, stocky, slow witted, bald man. Thank you….Oh, also.. my fiance died from licking toxic envelopes that I picked out. Thanks again.” (The Andrea Dorea)

8. George is seduced by a well-dressed woman who mistakes him for a rich businessman on the subway. She takes him to her hotel room, gets him to take off his clothes and handcuffs him to the bed. She then gets dressed, steals his wallet and, miffed at him only having eight dollars on him, decides to steal his clothes and leave him cuffed to the bed. “Will I see you again??” George cries as she exits. (The Subway)

7. George is petrified by the thought of Elaine starting to hang out with Susan. He explains to Jerry:

“Ah you have no idea of the magnitude of this thing! If she is allowed to infiltrate this world, then George Costanza as you know him, ceases to exist! You see, right now, I have Relationship George…but there is also Independent George. That’s the George you know, the George you grew up with–Movie George, Coffee Shop George, Liar
George, Bawdy George.”
“I love that George!”
“ME TOO!!!  And he’s DYING, Jerry! If Relationship George walks through this door, he will kill Independent George! A GEORGE DIVIDED AGAINST ITSELF CANNOT STAND!!!!” (The Pool Guy)

6. George explains to Jerry that his way of ingratiating himself to women is similar to the process used by a commercial jingle–annoying at first, then by the third date, it’s “Byyyy MEN–nen.”  Sure enough, later in the episode, he pisses off a woman on their first date, but weeks later, she calls him back, saying she couldn’t get him out of her head…”Coooo-STAN-za!” (The Chicken Roaster)

5. George, intrigued by the possibilities of his girlfriend’s vanilla-flavored incense, explores the possibility of combining food with sex, eventually going for the trifecta by adding TV as well. His girlfriend is extremely put off, but as he visits a friend of Elaine’s who is cooking up pastrami (“the most sensual of the cured meats”), she reveals herself to be as interested in achieving the hat trick as well. (The Blood)

4. George fights over a similarly-minded man for a parking space over an entire episode. Resolution is never reached, but clearly it is not a contest decided easily:

“Well, you’re going to have to go to the bathroom!”
“Well, you’re going to have to go to work!”
“I DON’T HAVE A JOB!!”
“NEITHER DO I!!!!!”

3. George pretends to be a Marine Biologist to impress the old “It Girl” from his college, but is put to the test when he and the girl come across a beached whale on their walk (“IS ANYBODY HERE A MARINE BIOLOGIST???“) We never see what happens, but George regales the gang with the story later:

“So I started to walk into the water. I won’t lie to you boys, I was terrified! But I pressed on and as I made my way passed the breakers a strange calm came over me. I don’t know if it was divine intervention, or the kinship of all living things, but I tell you Jerry–at that moment I was a marine biologist! […]  The sea was angry that day, my friends, like an old man trying to return soup at a deli! I got about fifty-feet out and then suddenly, the great beast appeared before me…I tell ya he was ten stories high if he was a foot. As if sensing my presence he gave out a big bellow. I said, “EEEEEASY BIG FELLA!” And then as I watched him struggling, I realized something was obstructing his breathing. From where I was standing, I could see directly into the eye of the great fish […]  Then from out of nowhere a huge title wave lifted, tossed like a cork and I found myself on top of him face to face with the blow-hole. I could barely see from all of the waves crashing down on top of me but I knew something was there so I reached my hand and pulled out the obstruction!” (Pulls out a golf ball Kramer had hit into the ocean earlier in the episode).

“Well, the crowd must have gone wild!”

“Oh yes, they did, Jerry. They were all over me. It was like Rocky 1. Diane came up to me, threw her arms around me, and kissed me. We both had tears streaming down our faces. I never saw anyone so beautiful. It was at that moment I decided to tell her I was not a marine biologist!”

“Wow! What’d she say!”

“She told me to go to hell and I took the bus home.” (The Marine Biologist)

2. George, dunked by one of his co-workers at an office meeting for eating too many shrimp (“You know, George, the ocean called…they’re running out of shrimp”), believes he’s come up with the absolutely perfect comeback (“Oh yeah? Well, the Jerk Store called, and they’re running out of you!”) Despite the prostestations and superior comebacks levied by all of his friends (and Kramer’s belief that he should just claim to have had sex with the jerk’s wife), George is certain that he’s come up with the zinger to end all zingers (“This is why I hate writing with a large group. Everybody has their own little opinions, and it all gets homogenized, and you lose the whole edge of it! I’m going with jerk store! Jerk store is the line! JERK STORE!!”) and even sets up another meeting (that he has to fly to) with the same jerk (and the same shrimp platter) to get the opportunity to use it.

The jerk repeats his zing, and George winds up and delivers the “Jerk Store” line. The jerk, a little quicker on his feet, responds: “What’s the difference? You’re their all-time best seller!” George, stunned and furious, instead reverts to the Kramer strategy: “Oh yeah? Well I had sex with your wife!!” George is informed that the jerk’s wife is in a coma, and that’s the end of that. But then, driving back to the airport, he mutters to himself “Well, the respirator called…” comes to a decision, and pulls the car back around for round three.

1. George, in the George moment to end all George moments, is at his girlfriend’s son’s birthday party, when a fire breaks out. He panics, pushes some kids and an old woman to the ground, and scampers out of the apartment without waiting for anyone else. Later, questioned by the firemen and attendees about his actions, he offers the following explanation:

George: “I…was trying to lead the way. We needed a leader! Someone to lead the way to safety!”
The Girlfriend:  “But you yelled ‘Get out of my way’!”
George: “Because!  Because, as the leader…if I die…then all hope is lost! Who would lead? The clown? Ha! Instead of castigating me, you should all be thanking me. What kind of a topsy-turvy world do we live in, where heroes are cast as villains? Brave men as cowards?..”
Girlfriend: “But I saw you push the women and children out of the way in a mad panic! I saw you knock them down! And when you ran out, you left everyone behind!”
George: “Seemingly. Seemingly, to the untrained eye, I can fully understand how you got that impression. What looked like pushing…what looked like knocking down…was a safety precaution! In a fire, you stay close to the ground, am I right? And when I ran out that door, I was not leaving anyone behind! Oh, quite the contrary! I risked my life making sure that exit was clear. Any other questions?”
Fireman: “How do you live with yourself?”
George: “…it’s not easy.”

Yeah. There’s no #2 to all that.

(The rest of the 100 Years, 50 Losers list can be read in its entirety here, and in case you just need a recap:

50. Matt McNamara, Nip/Tuck
49. The Dog, Foghorn Leghorn Cartoons
48. Xander Harris, Buffy the Vampire Slayer
47. DeAndra “Sweet Dee” Reynolds, It’s Always Sunny in Philadelphia
46. Cassidy “Beaver” Casablancas, Veronica Mars
45. Stuart Stevenson, Beavis & Butthead
44. Roz Doyle, Frasier
43. Hugo “Hurley” Reyes, LOST
42. Trent Lane, Daria
41. Andrea Zuckerman, Beverly Hills 90210

40. Landry Clarke, Friday Night Lights
39. Ted Buckland, Scrubs
38. Richie Cunningham, Happy Days
37. Cavemen, GEICO Commercials
36. X the Eliminator, Harvey Birdman: Attorney At Law
35. Bud Bundy, Married With Children
34. Jason, Home Movies
33. John Munch, Homicide: Life on the Street, Law & Order: SVU, …
32. Edgar Stiles, 24
31. Toby Flenderson, The Office (US)

30. Samuel “Screech” Powers, Saved By the Bell
29. George O’Malley, Grey’s Anatomy
28. Non-Alltel Cell-Phone Service Providers, Alltel Commercials
27. Bill Haverchuck, Freaks & Geeks
26. Cliff Clavin and Norm Peterson, Cheers
25. Meg Griffin, Family Guy
24. Jess Mariano, Gilmore Girls
23. Seth Cohen, The O.C.
22. Ziggy Sobotka, The Wire
21. Nelly/Lindsay Bluth Funke, Arrested Development

20. Bill Fontaine De la Tour Dauterive, King of the Hill
19. Murray Hewitt, Flight of the Conchords
18. Frank Rossitano, 30 Rock
17. Andy Botwin, Weeds
16. Carl Brutanananadilewski, Aqua Teen Hunger Force
15. Elaine Benes, Seinfeld
14. Phillip J. Fry, Futurama
13. Tim Canterbury, The Office (UK)
12. Charlie Kelly, It’s Always Sunny in Philadelphia
11. Enrique “Ricky” Vasquez, My So-Called Life

10. A.J. Soprano, The Sopranos
9. Turtle, Entourage
8. Trix Rabbit, Trix Commercialsa
7. George Michael Bluth, Arrested Development
6. Milhouse Van Houten, The Simpsons
5. Mark Corrigan, Peep Show
4. Thomas “Tom” Cat, Tom and Jerry cartoons
3. Coach John McGuirk, Home Movies
2. Brian Krakow, My So-Called Life
1. George Costanza, Seinfeld)

100 Years, 50 Losers: #2. Brian Krakow

“Why do you always have to say stuff like that?”

Brian Krakow, My So-Called Life

Played By: Devon Gummersall

Born to Lose: There has never been, and there will never be, a better teenage loser than Brian Krakow.

More and more, I think that My So-Called Life‘s primary innovations to the teen drama format are two-fold:

1. It only lasted one season (accidental, but innovation nonetheless–more on that later).
2. It wasn’t funny.

Not to say that there weren’t funny moments on the show, but any real sort of humor to be found in MSCL was more out of its gruesome identifiability than slapstick or situational comedy. And it’s not to say that shows like 90210, Dawson’s Creek and The O.C. were particularly riotous either, but they had occasional comedic subplots, and their tones were often light, breezy and almost nostalgic. Besides, their characters were usually very, very good at witty bantering.

Brian Krakow was not very good at witty bantering. In fact, most of the dialogue spewed from Brian’s mouth was what could most easily be identified as the exact opposite of witty banter. Dylan McKay, Pacey Witter, even Seth Cohen–these were characters who could talk up a storm, and on a good several occasions knew the exact right thing to say, and said it at the exact right time. Brian could talk up a storm too, but he never knew the right thing to say, and if he did, he certainly didn’t say it at anywhere near the right time. Nothing he said sparkled with the intelligence and sympathy that most losers are supposed to be compensated with. There were absolutely zero cute exchanges between Brian and Angela that made you say “Awww, if only she knew how good she had it with him!” Brian Krakow talks the way teenage loser males actually talk–or at least, the way they used to talk before they realized they were supposed to talk like Dylan, Pacey and Seth.

Despite rarely saying or doing the right thing over the course of the show’s one season, everything that Brian says or does feels pretty fucking right on–even down to his hair (long enough for him to hide behind, but too shaggy to be even accidentally fashionable) and his clothes (which scream “My mother buys my clothes for me, but she lets me choose the colors”)–both of which, incidentally, were definite staples of the IITS visual trademark in High School. His character is perfectly shaped as the kid in High School that everyone knew but no one really wanted to know that well–the kind of over-achiever that probably semi-secretly fantasizes about being a slacker, but will still berate you for talking too much in class if it means he can’t hear the teacher well enough to copy down his notes verbatim. His moves mark an essential lack of understanding when it comes to basic teenage codes, like about how you’re not supposed to raise your hand enthusiastically every time a question is posed in class, or about how nobody actually cares about what the yearbook looks like, or about how if the girl you like that’s treated you like dirt all your life asks you to give her a ride to the dance, she probably doesn’t mean it as a statement of romantic intention.

(Knowing the answers in life is far more important, Brian)

That last part of course is integral to the quintessential Brian Krakow episode, “Life of Brian,” the only one in the series narrated by his thought process. Consequently, you get such too-true and perfectly imperfectly articulated observations as “I became yearbook photographer because I liked the idea that I could sort of watch life without having to be part of it,” and “Finally, an erection from actual physical contact!” The crux of the episode involves Brian asking chubby classmate Delia Fischer (for such a loser, Brian did have two remarkably devoted admirers in Delia and Danielle, Angela’s sister) to the dance, but then canceling on her and breaking her heart once he misinterprets Angela asking him for a ride there as an invitation to love. The scene where Angela tries to explain why she needs the ride, but a too-ecstatic Brian can only concentrate on the lead, is gut-wrenching, as is Brian’s face when he sees a transfixing Angela walk down her stairwell (Claire Danes could clean up real nice).

It’s only a matter of time until he says something horrific, which he does once he tells Ricky not to hang out with them and then doesn’t even lie about doing so to Angela, who calls the situation half-correctly: “You don’t understand people, Krakow! You’re so heartless!” Naturally, Brian doesn’t have the good sense to cut his losses, and he tries to cozy back up to Delia, who’ll have none of it (possibly the one time on the show that any of its major characters shows anything loosely resembling self-respect). Then, once Angela realizes how cruel she had been to Brian, and asks him if he wants to dance, he can’t even manage to take advantage of her temporary sympathy, responding “Not with you.”

You get so used to Brian saying and doing the wrong thing that the one time he does say the right thing–which is pretty much only by accident–it’s the most stunning moment of the entire series. In the season finale, Brian gets enlisted by Jordan, Angela’s dreamy but borderline-dunce of an on-again, off-again beau, to write her love letters, supposedly from him. Despite being molasses-slow on his feet when it comes to speaking, Brian apparently has a real knack for playing Cyrano de Bergerac on paper, and the letters he write completely sweep Angela off her feet. It eventually gets out that Brian was in fact the one that wrote the letters, and Angela confronts him about the rumor, furious and confused. Brian, of course, tries to deny responsibility for the letters, until Angela fumes about the letter being a lie [from Jordan], and Brian–for one split second of happenstance–forgets himself, and responds “No, I meant every word.”

Angela, who over the previous 18 episodes has never given Brian one iota of mental or emotional consideration, gets frozen. She’s still furious, she’s still confused, but now she’s intrigued by Brian–which for Brian is the best progression that could have possibly happened in their relationship, and one that before this episode, he never could have hoped for. This is his moment. If he had followed up on it, told her how he’d loved her for years, how he’d wanted to say those things to her for so long, how he really really liked the way her shampoo smelled–she might not have swooned for him immediately, but at the very least, there’s no way she could’ve gone back to Jordan.

Instead, Brian balks. “I mean…the person who wrote it meant every word,” he amends his statement, slamming his own window shut. Soon after, Jordan shows to pick up the dazed Angela in his car, and Brian watches on his bike as they speed away. And that’s it. The show doesn’t get picked up for a second season, and we never find out if Brian ever follows up on his unintentional ground work–or, if, far more likely, Angela eventually convinces herself that Jordan wrote the letters, or that at the very least, he would have written them if he had Brian’s vocabulary and sentence-structuring abilities, and the two of them never really talk about it again. That’s why the show being only one season is so important–it didn’t stick around long enough to ruin itself. Because had the show gone on two or three or (God forbid) four seasons, eventually Brian and Angela would’ve ended up together, simply because you can’t have four seasons worth of TV show out of those characters without eventually hooking Brian and Angela up. And then Brian would’ve developed something disturbingly close to wit, and maybe they’d cut his hair, and before you know it, he’s a One Tree Hill character. No thanks.

There are so many reasons why there will never be another Brian Krakow. Partly in thanks to Adam Brody, you can now cast good-looking people as the loser as long as they talk faster than the rest of the cast, and partly in thanks to Judd Apatow, the loser has once again been re-ingrained into pop culture as the unlikely hero–both of which are arguably good things for loser culture, but both of which are unquestionably terrible things for artistically honest loser representation. Because now if you feature a loser–especially a younger one–in a leading role, you have to make them not only relatable, but overtly likable. You have to want to root for them. And even though you ultimately do end up rooting for Brian, it’s not because of what he says or does (since so few of his words and actions are anything but off-putting) but, rather, what he represents–a stage in adolescence where we’re old enough to know what we want, but not nearly mature or wise enough to know how to get it. And that’s infinitely more meaningful to me than cheering on Seth Rogen to do much of anything.

Partner in Loserdom: The two-per-show limit had more to do with MSCL than any other show on this list, since Angela, Jordan, Rayanne, even Danielle and Sharon all have pretty good claims to classic loser status. Sharon is actually probably the one closest to Brian, since she achieves the same kind of too-truthful annoyingness.

Real-Life Retribution: Somehow, Devon Gommersall ended up looking like this:

(Prev: #3 / Next: #1)

100 Years, 50 Losers: #3. Coach McGuirk

“Life sucks, Brendon. There’s your lesson. Go enjoy it.”

Coach John McGuirk, Home Movies

Voiced By: H. Jon Benjamin

Born to Lose: Coach McGuirk is just about as bleak a projection of adult loserhood as exists without being overtly depressing. McGuirk lives by himself, has zero romantic success (aside from Paula’s nutty friend, with whom he almost hooks up with twice–once where he chickens out, and once where he has a heart attack), hates his job as a soccer coach (except when he can blackmail his students into doing favors for him with the threat of bad grades), and fails miserably in his various other ambitions (including stand-up comedy, psychic fortune telling and driving a car onto the stage in the middle of a play). He’s not well-liked, he’s not taken seriously by anyone, and he’s in typical middle-aged gym-teacher shape–he should be virtually unwatchable for those of us slightly worried about projections of our own lives twenty years down the line.

Nonetheless, McGuirk is not only Home Movies‘ best, most compelling character (and the show has a pretty good claim to being maybe the second best animated TV show of all time), but one of the funniest characters in TV history. Mostly I feel this is because most TV shows tend to take aging, prospect-less losers and go one of two directions with them–to ennoble them and make them pathetically kind to everyone, or to embitter them and make them unnervingly nasty to everyone. McGuirk, on the other hand, is neither of these–he’s certainly not overly gregarious, since he tends to insult or take advantage of the only people who can even stand him. But he’s not really that bitter, either–he’s not thrilled about his station in life, sure, but he doesn’t seem to mind an existence consisting mostly of going to the mall drunk and undergoing degrading science experiments for free DVD players all that much.

Grounding McGuirk’s character, of course, is his relationship with Brendon, who lacks a father figure for most of the show’s run (he has a real dad who shows up midway through the second season, and who’s actually a pretty decent guy, but is always busy with his work and ends up marrying a real wench). Brendon comes to McGuirk for advice on most of his life’s problems, ranging from flunking history class to fighting with his friends to sucking at the guitar, and McGuirk’s advice is usually terrible to the point of genuine destructiveness, but Brendon doesn’t seem to hold it against him that much–he’s smart enough most of the time to know when the Coach has no idea what he’s talking about, and just seems appreciative enough of his effort to keep coming back to him in future episodes. And every so often, the Coach legitimately hits one out of the park, as when he correctly pins Brendon’s issues with his future mother-in-law to his own burgeoning attraction to her, or when he smartly advises Brendon on how to handle the school’s new lethario Octavio when it becomes obvious that he’s using Melissa.

It’s a very touching relationship, but one that never even borders on sentimentality. He clearly cares about Brendon, but has an awful way of showing it–like when he gets (well, steals) Brendon a bike, but takes it back when he realizes Brendon’s father had already gotetn him one–and often fails to come through for Brendon when it’s inconvenient for him to do so. He’s even a little too liable to kick Brendon when he’s down, as when he tells Brendon during the middle of his disastrous production of the school play, “It’s kind of a disaster….like, a historic disaster. And that’s good…in a way…because you’ll be sort of famous, for putting on the worst play ever in this elementary school.” Still, Brendon’s clearly the closest thing to family that McGuirk has, and he seems to understand that, often showing up unannounced and unwanted at the Small’s residence, even if he doesn’t act the part as well as he should.

And all that shit aside, the dude just is just at the center of some seriously hilarious moments. There’s the episode where McGuirk accidentally goes on a soujurn in the woods with a man-love cult and ends up eating poison berries and going crazy (his first words upon being discovered by Brendon, Jason and Melissa at a nearby overnight camp: “Brendon, eat these berries. They’re poisonous”). There’s the episode where he shows up at Fenton’s birthday party and ends up teaching the kids how to (incorrectly) play dice, taking all of their money and impressing Fenton’s mom. And then there’s my all-time favorite Coach McGuirk moment, where when taking a contemplative walk on the beach, Brendon trips over an extremely hung over and sunburned McGuirk (hidden under a bunch of weeds), who asks him “Brendon, what are you doing in my house?” Brendon responds that he’s on the beach, and McGuirk amends his question, “What are doing on my beach?” He then looks around, thinks to himself for a second, and puts his head in his hands: “Oh, man, not again.”

Adversary in Loserdom: A lot of my favorite Home Movies episodes are centered around the dynamic between McGuirk and Brendan’s significantly more bookish school teacher, Mr. Lynch. As the only other member of the staff that tends to tolerate McGuirk, he often gets cajoled or bullied into McGurik’s plans–double dates, discount trips to Mexico, inner-circle corruption–and though they start out hating each other, he and McGuirk usually work up a bizarrely compelling bond by the end of their episodes. It’s the closest thing Home Movies has to those great Brian-Stewie “Road To ___” Family Guy eps.

Some More Quotes For the Hell of It: “Brendon, there’s nothing wrong with lying to women. Or the government. Or parents. Or God.”

“Now when I was in college I went through some weird times…I ran with a gang. The gang was called the Feelgoods. It wasn’t the toughtest gang in the world… it was more like running with the cast of a broadway musical. Very annoying. A lot of freaky interpretive dance stuff – beads, makeup – in other words, DRUGS, Brendon…”

“Per day, I would say I hate far more than I feel like I like something. I like my western omelet, but while I’m eating that there’s about 17 other things that I hate, like my apartment, my breath, whatever’s on the TV, whatever’s in the paper. Then I walk outside and it’ll be a nice day. Well that’s great that’s a good feeling for a split second and then I realize I hate my neighborhood, because I… you apparently can’t play music after 6:00 pm… in this country…”

“THIS IS WHY MUSIC IS EVIL!!!!”

(Prev: #4 / Next: #2)

100 Years, 50 Losers: #4. Thomas “Tom” Cat

Don’t you believe it

Thomas “Tom” Cat, Tom and Jerry cartoons

Voiced By: William Hanna, Allen Swift, Mel Blanc, others

Born to Lose: There was a girl I knew back in high school who I was friends-through-friends with, but hadn’t come down with a conclusive opinion on, until one day we were in a comics store with a bunch of our friends and they started showing some Tom & Jerry episodes. As I was wont to do whenever the subject came up, I started ranting about how Tom was the real hero of those cartoons and what a poor sap he was compared to an evil mastermind like Jerry. The girl stared at me uncomprehendingly and said she thought Jerry was the more relateable character. It became suddenly and disturbingly clear that this girl and I were going to have issues. (I was definitely right, though to her credit, six years and a decent amount of drama later, she turned out to be a pretty OK person).

I couldn’t tell you how the dynamic between Tom and Jerry started–I’ve never watched the series straight through, exactly–but to me, it’s abundantly clear that in their relationship, Jerry is the aggressor and Tom is the patsy. What reason does Tom have to want to chase Jerry? It’s not culinary–even on the rare instances that he actually catches him, he never actually tries to eat, or even kill him. And it’s not like Tom seems like an inherently violent person–whenever he’s not in pursuit of Jerry, he’s basically nothing more than a less cynical Garfield, just laying about the house, eating elaborate sandwiches, romancing female cats, not a care in the world. Possibly it started out as Tom just chasing Jerry on species instinct, but even if so, it was never personal with Tom.

Jerry, on the other hand, is a straight-up sadist. Much smarter than his supposed “tormentor,” Jerry spends the majority of most T&J episodes plotting little schemes to get Tom shaved, electrocuted, beaten up, and to just all-out ruin his lazy afternoon. Unlike the Roadrunner, who was forced to get Wile E. Coyote to blow himself up and run himself off of cliffs out of self-defense (although he never seemed particularly threatened by WEC, given his Lions-esque win/loss record), Jerry is usually the one who starts shit–out of malice, out of boredom, who knows. Usually, the only times Tom acts out against Jerry is out of revenge and annoyance for when Jerry tries to frame him for destroying the curtains with the house maid, or when he disrupts his naptime by catching his nose in a mousetrap, or pantses him in front of the girl he’s crushing on. I mean, if some little punk was doing that kind of crap to you–and you were about five times his size–wouldn’t you want to do something about it?

(Jerry forms a pre-emptive alliance with a fellow pissant)

Now, not that Tom is a particularly righteous individual–he clearly leads an extremely self-centered existence, and he maybe has a little too short a temper (why not just calm down, collect some evidence, and alert the maid to all of Jerry’s misdoings?) But I mean, he seems like a decent-enough guy–especially by cat standards, since even the most gregarious of their sorts are still by nature narcissistic and tempermental. Meanwhile, not only does Jerry constantly disrupt Tom’s peaceful serenity, but he has that expression on his face while doing so–that smug, self-satisfied, shit-eater smile that makes you want to punch its wearer, no matter who it is. Jerry’s like your little eight-year-old Damien of a third-cousin, the kid who’ll kick you in the shin for no apparent reason and just smile at you for it like he just gave you a Christmas present–except you can’t go and knee him in the groin in vengeance because the rest of your family will always take his side.

You can’t compete with someone like that, because even when you win, you lose. And that’s the story of Tom’s life–permanently fighitng a war that he didn’t ask for, and one which always ends with him shaved, sore-assed and electrocuted.

Partner in Loserdom: Obviously I’m far from the first to point out the evil and psychosis involved in the Tom and Jerry dynamic–The Simpsons did it far better than I ever could with the entire Itchy & Scratchy subplot, in which the timid, mild-mannered and somewhat sentimental Scratchy is not just tormented, but murdered and usually gruesomely dismembered by the sociopathic Itchy. Interestingly, I&C seems to suggest a sort of psychosexual aspect to their relationship, as Scratchy often appears to be weirdly in love with Itchy, implying a kind of domestic abuse or possibly extreme-S&M basis to their relationship. Wonder what Hanna-Barbara would’ve thought about that.

(Prev: #5 / Next: #3)

100 Years, 50 Losers: #5. Mark Corrigan

“Life’s all pain. Pain, gloom and misery… Hey, 33% extra free. I am doing excellent shopping. My depressed state of mind means being even more frugal than usual.”

Mark Corrigan, Peep Show

Played By: David Mitchell

Born to Lose: Shut up, brain, or I’ll stab you with a Q-Tip. There are losers, and then there are losers, and then there are characters that hit so close to home that you can’t even force yourself to watch through the fifth season. Mark Corrigan lands squarely in the latter category–not just because of what he says or what he does, because of what he thinks. Most TV shows are kind enough not to let you hear the depraved and miserable thoughts of their most depraved and miserable characters, but Peep Show performs no such niceties with its two principal characters, Mark and Jeremy. Now, Jeremy is a loser too, no doubt–he can’t keep a job for more than an episode, his experimentation with drugs and sex always leads to disaster, and his constant desire to seem cool to everyone leads to such hilarious moments as a wasted Jez, trying to look like a badass by drinking beer at the grocery store, attempting to hit on the cashier: “Hold your horses, honey–I’ve got coupons for the Pringles.” Nonetheless, Jeremy is good-looking and successful with women (and occasionally dudes) enough that he is clearly the lesser of two losers here.

Mark, on the other hand, is a complete mess. He has a decent job (though I couldn’t possibly tell you what he does, besides occasionally fuck up presentations, piss in his supervisor’s office and try to hack his crush of a co-worker’s e-mail account), but his life is utterly dominated by his constant anxieties–about his job, looks, sexuality, testicles, stage of life, co-workers, and for a couple seasons, his girlfriend. We know this, of course, because all of these anxieties are vocalized as Mark narrataes his own thought processes, allowing us to share his endless supply of mini-crises as he frets about whether current crushes are “the one” and contemplates what various WWII-era leaders would do were they in his situation. Mark is a character who reminds us that whenever we are happy or content with a particular aspect of our existence, there’s probably still something there to be panicked about, and even if not, all the other aspects of your life are probably fucked up enough that you shouldn’t dwell on the positives of this one for too long. And yes, by the way, this show is a comedy.

Mark’s loser credentials peak for me in the fourth season (excuse me, series), as his wedding date with accidental-fiancee Sophie (he planned to propose to her, decided that he didn’t like her that much, she found the ring, he was too embarrassed and entranced with her summer estate to explain the mix-up) approaches. With echoes of another legendary TV loser, he spends the season trying to find excuses to weasel out of it, but can’t get anything to stick, until the wedding day actually comes, and he tries to hide with Jez ifrom his bride ndefinitely in the church rafters. Except Jez has to take a piss, but since he can’t go to the bathroom without giving away his and Mark’s location, he pisses in the rafters, and as it drips down onto the attendees underneath, Mark has no choice but to announce his location, playing it off like a joke. Despite giving his game away completely, he still can’t get up the nerve to cancel the ceremony, and they actually get married, until a tearful Sophie runs away from their honeymoon vehicle, exclaiming “HE’S HORRIBLE!” Mark, of course, is endlessly relieved. It’s pathetic, it’s despicable, and it’s borderline unwatchable. It’s also, of course, the way I would be very likely to behave were I in the same situation. Hey, there’s a reason I can’t get through that new season.

The moments like this abound in the show–cringe-worthy scenes of Mark, about to seal the deal with Sophie for the first time, instead telling her off for some mildly irksome thing she did earlier in the episode, or him testing his sexuality with rented gay porn after worrying about crushing on his male boss, or him escaping out the window of a big meeting due to being completely unprepared for it, only to return the same way after realizing what a big mistake he made, despite still having absolutely nothing to present. Moments that defy easy explanation–despite the fact that Mark’s brain is pretty much explaining his motivations every step of the way—moments which are depressing and pitiable and often a little unnverving, but still manage to be just funny enough in their realism that they’re somehow still watchable. Mark makes Larry David look like Steve Sanders, and we should be grateful to him for giving the rest of the world–or the UK, at least–insight into our disturbing mental condition.

Moment of Triumph: There are two that stand out, one of which comes courtesy one of my and Mark’s most-shared anxieties–the belief and fear that everyone younger than us is secretly (or, rather, completely not-secretly) plotting against us–when he gets his phone and wallen stolen by a bunch of teenage hoods with knives. He sees one in the movie theater on a date with Sophie, and uses his flood of anxiety to give him enough of an adrenaline rush so that he pops the little pissant in his mouth–turning on Sophie to no end, and permitting Mark to get hard again in her presence for the first time in weeks (the triumph of this is quickly undone when Sophie discovers the knife Mark now carries for protection and thinks him a psycho). But for my money, Mark’s ultimate moment of triumph comes when he fakes doing Ecstasy with a now drug-dependent Sophie and her idiot raver friends, advised by Jez that all people do when they’re on E is dance, touch each other and talk about how the world would be better without all of its systems. At the end of the evening, with Sophie and her friends now back at his place, Mark eventually gets fed up, breaks the ruse, kicks everyone out, and offers Sophie’s very disappointed friends the following words of wisdom:

“While we’re at it, there are systems for a reason in this world, economic stability, interest rates, growth. It’s not all a conspiracy to keep you in little boxes, alright? It’s only the miracle of consumer capitalism that means you’re not lying in your own shit, dying at 43 with rotten teeth and a little pill with a chicken on it is not going to change that. Now come on, fuck off.”

Personal Loser Bond (NOT FOR THE FAINT OF HEART):

Once, the morning after drinking heavily on my roommate’s birthday party, he and his girlfriend were in the shower when I realized I had to take a shit worse than I ever had before in my life. I tried to mind-over-matter it for about ten minutes until I realized that I had the choice of either introducing myself to my neighbors via a huge dump in their toilet, interrupting my roommate and his gf and politely asking them to clear out, or going somewhere in our apartment. My mind immediately flashed to Mark in a season three episode, getting locked in his room by Jeremy while he’s ill so he doesn’t disrupt Jez’s mushroom party, and having a similar dilemma, with the following thought process while contemplating shitting in his room:

“If I do this, well… even if I end up marrying Sophie and we live in a detached house in Surrey and buy a holiday home in Umbria, our children will always look up at the face of a man who once crapped in a takeaway bag. Plus I’d have to hide it here somewhere in my room next to one of my things…Well I could throw it out the window…NO! That’s what they want you to do–thats where society’s headed! People shitting in bags and throwing them out the window–well I’m not going to be the first! NOT IN MY NAME!!!”

Unfortuantely, I lacked Mark’s discipline, and ended up going in one of my trashbaskets, locking myself in my room until my roommate and his girlfriend left, then septuple-bagging the trash bag and taking it outside.

(Prev: #10-6 / Next: #4)

100 Years, 50 Losers: #10 – #6

#10.

A.J. Soprano, The Sopranos

Played By: Robert Iler, Jr.

Born to Lose: Forget a ne’er do well–A.J.’s a ne’er do anything remotely correct. Well, that’s not completely true–over the course of six (really seven) seasons, Anthony Soprano, Jr. does a grand total of three things right. In season three, he recovers a fumble for his football team. In season five, he puts on a profitable frat party (albeit one that ends up in a brawl). And in season six, he bribes a bunch of loud thugs to be quiet, and is rewarded with sex from his date for his efforts. That’s it. Besides that, he gets into fights with bigger kids, misinterprets (and mispronounces) Nietzche, flunks High School English, plans a half-assed assassination attempt on his great-uncle, gets his eyebrows shaved off by his friends, gets caught vandalizing the school swimming pool, cries for his mommy at the sight of a bear in the backyard, sets his car on fire, flunks out of college, grows a Lars Ulrich hairdo, misguidedly proposes to his one-foot-out-the-door girlfriend, and passes out a whole bunch of times. Of course, the show saves A.J.’s coup de grace for one of the last episodes, when he even fails to properly kill himself, attaching a brick with a too-long length of rope to his leg, jumping in the family pool, and just flailing around for a minute until Daddy comes out to save the day. For all of the horrific things that Tony Sr. does over the course of the show’s run, the fact the he continues to put up with two family members that are veritable Worst Case Scenarios–an ungrateful, domineering, possibly demonic mother like Livia and a spoiled, lazy malcontent of a son like A.J. (the sight of him loafing on the couch, chuckling at an episode of Aqua Teen Hunger Force while his parents watch on in confusion and disgust, is one of the series’s most indelible)–goes a long way towards making up for them.

Too Close to Home: Robert Iler, Jr.’s rap sheet is almost as impressive as A.J.’s, getting busted for attending an underground poker club and for the armed robbery–in ’01, still the height of SopranoMania–of a couple of Brazillian tourists. Think maybe there’s a reason you never see Bobby in other acting roles?

#9.

Turtle, Entourage

Played By: Jerry Ferrara

Born to Lose: Turtle might come closer than anyone on this list to obtaining the title of “Professional Loser”–an innovation which we can all respect and appreciate. Turtle doesn’t really do anything but smoke pot, party and chase girls, but his networking abilities and shamelessness regarding those three things make him a useful enough asset that when his actor friend hit it superbig, Vinny put Turtle on the payroll. Consequently, Turtle became a loser with an almost bottomless budget, allowing him resources the likes of which most of us can only dream in the pursuit of getting high, drunk and laid. In the first article he wrote about Entourage, Bill Simmons said that in a real life Entourage, Turtle would constantly be angling for E’s position, and while that may be true, Turtle’s lack of personal ambition makes perfect sense to me–if you could just hang back and leech of your good friend while he did all the work and you got to enjoy all the benefits, why would you wanna fuck with that? Especially when you have a partner in crime like Johnny Drama to work with-an equally shameless running partner with some spectacular loser credentials himself. Besides, Entourage is at heart as pure a fantasy show as they come, and in Turtle, those of us without any particular God-given talents or looks get someone whose existence we can pragmatically fantasize about having.

Real-Life Retribution: Not only does Turtle eventually get with Jamie Lynn-Sigler (a.k.a A.J. Soprano’s much hotter and more successful older sister) in the show, but Jerry Ferrara eventualy gets with her in real life, too. I guess Meadow turned out to be a much bigger fan of hip-hop, pot and the Yankees than we all could’ve anticipated.

#8.

Trix Rabbit, Trix Commercials

Voiced By: Mort Marshall / Russell Horton

Born to Lose: What is there to say? In terms of the strictest definition of the word loser–as in, one who fails at the achievement of his or her most prized goals–there is no bigger loser on TV, or in any other medium for that matter, than the Trix Rabbit. Does he need oxygen? Maybe. Does he need the love of a good woman? Doubtful. Does he need clothes? Almost certainly not. He has but one need in this world, one craving, one desire–for some fruity, puffy, mediocre cereal. And to that end, there is basically no measure to which the rabbit–disguises, fake accents, cross-dressing, possibly some socially acceptable forms of prostitution–will not go. Yet despite this, the rabbit is perpetually thwarted in this obsessive, singular pursuit, denied the only thing he wants by a bunch of vicious, mean little breakfast-hoarding shits with opposable thumbs. And why? Social prejudice of the most debasing, disgraceful order–species discrimination that you’d have to think the producers would never be able to get away with in this day and age. Tony the Tiger never appears to have to fill out any paper work to lay rightful claim to his Frosted Flakes, and Toucan Sam can follow his nose to Fruit Loops whenever he damn well pleases, but the Trix rabbit remains eternally unsatisfied.

Unkonwn Depths and Complexities: Apaprently the cereal-buying public did take sympathy enough on poor Trixie to vote “Yes” on a nationwide poll taken in the early 90s over whether or not he should finally be reunited with his beloved, resulting in him finally getting to eat a bowl in ’91. That bowl only having fed his obsession further, however, he has not been the recepient of more than a single spoonful since.

#7.

George Michael Bluth, Arrested Development

Played By: Michael Cera

Born to Lose: Or, where a nation of awkward post-adolescent males finally found the poster boy they had been searching for for so long. I remember the exact moment I fell for George Michael–playing cards with Maeby at the end of the pilot episode, his circuits having been completely scrambled by his kiss with his cousin (initiated by Maeby in an unsuccessful attempt to piss off her parents):

George Michael: “I’m tempted to kiss again just so we could teach them a lesson!”
Maeby: “And…why would that teach them a lesson?”
GM: “Oh, uh, I mean, to freak them out.”
Maeby: “Yeah? But that doesn’t make any sense… ”
GM: “Well, isn’t that what makes it funny? I’m laughing. Go fish. Uno. Uh, I gotta finish this drink.”

This was not TV awkwardness. This was not TV anything. This simply could not be taught, only lived. There was no disguising it–George Michael was one of us.

Over three glorious seasons, George Michael represented us at our most confused, our most uncomfortable, and our least athletic. His tragic dilemma–being in love with his father’s sister’s daughter–was the real meat of his character, leading to numerous classic lines (“Cousins can bunk together! That’s why they call it ‘Bunking Cousins!'”) and even classicer subplots (Les Cousins Dangereux, anyone?) But George Michael was George Michael in absolutely everything he did, from reflexively turning away and shrinking whenever someone throws something at him to re-enacting the Star Wars Kid video in his garage to his response to his girlfriend dumping him, when he just collapses and folds while walking in his living room–probably one of the ten funniest things ever to be shown on TV. As the show went on and nearly every character became grating and borderline-intolerable, we never got sick of George Michael. And until Nick and Norah’s Infinite Playlist, we thought we never would.

Moment of Triumph:

#6.

Milhouse Van Hauten, The Simpsons

Voiced By: Pamela Hayden

Born to Lose: C’mon, say it with me now: “NOBODY LIKES MILHOUSE!!” It’s rare that a TV show reserves a character almost purely for punching bag purposes, but The Simpsons’ let loose on Milhouse like no other. Picked on by bullies, teachers, psychiatrists, his friends and their parents (Milhouse even gets placed by Bart on the FBI’s Most Wanted list in one episode), the few people whose attention he craves–like unrequited crush Lisa, who considers him more of a big sister than a romantic prospect (“NO I’M NOT!! WHY DOES EVERYONE KEEP SAYING THAT???“)–tend to have better things on their mind. Meanwhile, his future looks to be even more dismal than his present, as Principal Skinner elects to swap Bart’s permanent record (“[which] will one day disqualify you from all but the noisiest, hottest jobs”) with Milhouse’s to bribe Bart to keep quiet about his relationship with Edna, and then there’s all those projections about Milhouse turning out gay (despite his torrid but short-lived smoochfest of an affair with one-off girlfriend Samantha). Eventually, he apparently does get to sleep with Lisa, but is written out of history by Lisa and Marge on the former’s wedding day (“Oh, Milhouse doesn’t count”), while he ends up working as Homer’s hardass supervisor at the Power Plant. If Milhouse ever actually won, though, it’d be borderline tragic–what good is a punching bag that punches back, anyway?

Ultimate Low Point: The entire Summer of 4 Ft. 2 episode, where Bart, Lisa and Milhouse vacation with the Simpson parents in Little Pwagmattesquarmsettport. Bart and Lisa argue and threaten each other heatedly while ignoring Milhouse (hidden behind a box of cereal) completely. Bart and Lisa spit at each other on an amusement park ride, and somehow both of their spit ends up hitting Milhouse. Bart, Marge and Homer play Mystery Date, and when Bart draws the “dud” date, Homer exclaims at Milhouse “He looks like you, Pointedexter!” Finally, when they’re driving back to Springfield and Lisa admires all the signatures of her new friends in her yearbook, she disdains the final signature in the corner: “See you in the car! – Milhouse”

(Prev: #15-11 / Next: #5)

100 Years, 50 Losers: #15 – 11

#15.

Elaine Benes, Seinfeld

Played By: Julia Louis-Dreyfuss

Born to Lose: It’s my firm belief that Elaine was the most underrated of the big Seinfeld four. Given the unenviable task of pretty much representing the entire female gender on a largely male-dominated show, Elaine was still one of the show’s funniest characters, a woman dissatisfied with her place in the world–she hates her employers, she hates her friends, she hates most of the guys she ends up with–but too jaded and lazy to do anything about it. She was good-looking, but not so much so that it was unrealistic that her idiot male friends could consider her an unsexualized equal, and generally give her as much shit as they give each other–one of my favorite Elaine memories is when Jerry keeps betting on her backsliding in her relationship with Puddy, and cackles with a cigar in his mouth as Elaine keeps shelling out money–and the model of that dynamic was extremely influential on at least a couple of the other female losers on this list. Professionally she was moderately successful, but she wasn’t above making a scene out of herself, drunkenly making out with co-workers at weddings, refusing to take off her Orioles cap at Yankees games and dancing blissfully arrhythmically at company functions. Years before Sex and the City, she offered a slightly less magical, but arguably more cost-effective representation of the single woman in the Big Apple.

Ultimate Low Point: You gotta love the episode where Elaine stops having sex and gets more and more stupid, guffawing at her boyfriend’s answer to the Crossword clue “Winnie the ___.”

#14.

Philip J. Fry, Futurama

Voiced By: Billy West

Born to Lose: Despite what many may tell you, Futurama was not a great show. In fact, especially considering that I’ve seen every episode multiple times, it really was barely even a particularly good show. The plots were mostly unmemorable, the satire was lame and the rest of the humor was often mediocre, and a lot of the characters (Zoidberg, Bender, Zap) ranged from overrated to downright grating. The fact that people exist that consider the show equal or superior to The Simpsons keeps me up at night. But even at its worst, the show was always at least watchable, and that was largely due to Fry–the show’s core, and its one legitimately great character. There wasn’t anything hugely special about Fry–he was just some average dude in his 20s with a lousy job and a fed-up girlfriend that happened to get frozen in time for 1000 years. But the way he experienced all the goings-on in Futurama–the combination of wide-eyed wonder and “yeah, I guess I can buy that” amicabilitymade him the perfect protagonist for the show, a guy who, like much of the audience, was so little enamored with his world in the year 2000 that he was perfectly willing to roll with the punches of a completely new and strange universe. Add in the fact that he was the show’s only emotionally compelling character–the episodes involving his unrequited love for Leela and his sadness over his old dog Seymour are among the show’s most beloved–and it’s amazing that the guy doesn’t get more credit for as doing much for Futurama as he does.

Unlikely Loser Branding: I never really understood what it said about Fry that his favorite song was Katrina + the Waves’ “Walking on Sunshine,” giving the song more exposure than it would get until a whole lot of tasteless jokes got it back in the public consciousness in 2005.

#13.

Tim Canterbury, The Office (UK)

Played By: Martin Freeman

Born to Lose: The gap between Tim and Jim is one of the quintessential points of differentiation in between the US and UK versions of The Office. Same basic character, of course–mid-level office worker with a contempt for a lot of his co-workers and an (at first) unrequited affinity for the office secretary. But there’s an edge to Tim that Jim doesn’t really have–my ex-roommate, upon viewing the American version for the first time, pointed out that Jim “was basically a frattier version of Tim,” and while I dunno if I’d quite put it like that, the sentiment is pretty right. Jim hates his job and hurts for Pam, sure, but you feel like he’s probably got his life pretty together besides, and his smugness seems based more on a feeling of superiority than a legitimate bitterness. Tim, on the other hand, has a snap to his pranks and snipings at co-workers that reflects a genuine anger, and based on his conversations about his mentally ill father and his claims to having no friends, you get the feeling like his home life is similarly frustrating and unsatisfying. He even looks significantly more desperate than Jim (and is, in fact, about a half-decade older), who is too shaggy and adorable for you to ever really pity him. When he finally hooks up with Dawn at the end of the show’s run–in maybe one of the ten best moments in all of TV history–you’re not just thrilled because he got the girl, you’re also just glad that he now has a reason to live.

Classic Loser Quote: “No I don’t talk about my love life for a very good reason, and that reason is I don’t have one. Which is very good news for the ladies-I am still available. I’m a heck of a catch, cos, er well look at it. I live in Slough, in a lovely house, with my parents. I have my own room, which I’ve had since yep, since I was born. That’s seen a lot of action I tell you. Mainly dusting. I went to university for a year as well, before I dropped out, so I’m a quitter. So, er, form an orderly queue ladies.”

#12.

Charlie Kelly, It’s Always Sunny in Philadelphia

Played By: Charlie Day

Born to Lose: Maybe the most promising new loser to come out of TV in the last few years, Charlie is also probably the most consistenly hilarious character of any sort on TV right now. Sunny is another one of those “everyone’s a loser to some extent” shows, but there’s absolutely no doubt who the odd one out in this bunch is. Nervous, impulsive, constantly drunk and essentially illiterate, Charlie consistently goes that extra mile to put that final level of desperation between him and the rest of the gang at Paddy’s. He sniffs glue, he lives in unmentionable squalor, he writes insane story songs that he makes even more insane musicals out of, and with nothing but the most negative of reinforcement, he continues to unreciprocatedly obsess over the same waitress to the point of obvious stalkerdom. And he also makes himself one hell of a human guinea pig, whether he’s pretending to be a crippled veteran to get sympathy at a strip club or getting chairs broken on him and popping steroid pills to prepare himself for underground street fights. Everyone always says that It’s Always Sunny in Philadelphia is “like Seinfeld on crack,” a description I generally fiend too flattering–but for Charlie’s character, it might actually be something of an understatement. Double points for making Green Man one of the classic loser Halloween costumes, as well.

Real-Life Retribution: In one of the all-time real life loser triumphs, Charlie Day is married to Mary Elizabeth Ellis, the supercute chick who plays the Waitress. Danny DeVito’s jealousy on the DVD commentaries is disturbingly palpable.

#11.

Enrique “Ricky” Vasquez, My So-Called Life

Played By: Wilson Cruz

Born to Lose: Most of the characters on this list are loveable schlubs, generally untragic figures good for a decent self-effacing laugh or two. There is absolutely nothing funny about Ricky Vasquez. Even Bill Dauterive is basically a carefree, happy-go-lucky individual compared to Ricky, a gay teen in Pittsburgh with little but soul-crushing misery to be found in his nineteen episodes on My So-Called Life. Points to the show for not really making him a target of school bullying or anything so obvious–truth is that by the time he got to high school, an extroverted kid like Ricky wouldn’t still be getting picked on by the school’s more fortunate. Instead, Ricky just gets ignored by everyone except his two closest friends, barely even a blip on the radar of a school that doesn’t really understand what the deal with homosexuality is, and doesn’t much care to find out. Meanwhile, he gets beaten up and kicked out of the house at home, and has to show up at his English teacher’s door because he has no other options. No doubt Ricky would’ve had the time of his life once he got to college, and it’s even likely that had MSCL gotten a second season, they would’ve eventually at least thrown him some sexually ambiguous new kid to flirt with, but instead the lasting legacy of Ricky Vasquez is that of the permanent outcast, who not only can’t see a way out, but doesn’t even know to hope that somewhere there exists the slightest chance of a way out. Loserdom isn’t always pretty, kids.

Moment of Triumph: Moments after being humiliated at the school dance, and delivering the most heartbreaking monologue in a series full of ’em (“You know, that..I belong nowhere. With no one. That I just don’t…fit”), Ricky teams up with the similarly jilted Delia Fischer to perform a stunningly emotional tango and grind to the strains of Haddaway’s “What is Love?” while the entire school stares and applauds. In a remotely just world, this is the TV moment that the 90s one-hit wonder would’ve been inextricaly linked to.

(Prev: #20-16 / Next: #10-6)

100 Years, 50 Losers: #20 – #16

#20.

Bill Fontaine De la Tour Dauterive, King of the Hill

Voiced By: Stephen Root

Born to Lose: Poor, poor Bill. Quite possibly the most underrated character on King of the Hill, lacking the gimmickry of Boomhauer or the non-stop yuks of Dale, Bill was the quiet conscience of the show, a guy who had suffered so much in his recent life that he knew he was in no place to judge just about anyone for anything. In a more practical sense, Bill also served as the doormat for the show’s other characters, who clearly sympathize with their friend and neighbor’s plight–a deadly combination of post-divorce loneliness, faded-glory High School nostalgia and professional dissatisfaction–but have long since lost interest in humoring his self-pity. Consequently, Bill is possibly the most visibly downtrodden character in recent television–the kind of character that becomes even more depressing when he smiles because it provides such a stark contrast to the norm. Bill is the ex-Texas football star you never seem to see in Varsity Blues and its ilk–the guy who’s been beaten down by his underwhelming adult life, but rather than become embittered by it, just closes his blinds at night and sobs to himself. Heartbreakingly hilarious stuff.

Moment of Triumph: Surprisingly, Bill does have a couple to choose from, but I’d have to go with one of my favorite episodes, where he rejoins the Arlen football team on an eligibility technicality to re-tie his unfairly broken touchdown record as the Bill-dozer’s finest moment.

#19.

Murray Hewitt, Flight of the Conchords

Played By: Rhys Darby

Born to Lose: Murray is something of a precednet-setter in the loser community: A successful 9 to 5er whose secret passion–nay, secret identity–is as a loser. You never see particularly much of what Murray does in his position as Deputy Cultural Attache at the New Zealand consulate, but you get the feeling that he’s probably pretty good at what he does, and that he’s probably well-compensated for it, too. Despite this, somewhere along the line, he decided to start moonlighting as the manager of Kiwi-country’s fourth most popular folk parody duo–despite the fact that the band is monstrously unsuccessful, he has no visible talent as a promoter or manager, and he doesn’t even appear to understand or like music. Since then, he’s lost his wife, with all attempts at reconciliation ruined by his self-imposed obligations to the band, and all he appears to do at work is hawk the latest Flight of the Conchords merchandise. It’s a compelling, and arguably far more pragmatic, inversion of the cliche of the importance of following your dreams, since Murray’s pathetic attempts to live the Rock and Roll Lifestyle just get in the way of what should probably be a fairly rewarding existence and steers him directly down the unmistakable path of unglamorous loserdom.

Breaking the Cycle: Murray’s ambitions do, against all odds, eventually come to fruition, due to the enormous crossover success of fellow clients The Crazy Dogggz’s smash “The Doggy Bounce,” after which it is implied that Murray abandons the band and rides the Dogggz’s coattails to fame and fortune, thus making a second season of the show a remarkably tricky prospect.

#18.

Frank Rossitano, 30 Rock

Played By: Judah Frieldnader

Born to Lose: Fat, crude, and with no evident social life to speak of, Frank nevertheless represents the very personification of what could be called the Loser Id. Many may choose to view the loser lifestyle as one that is foisted upon its constituents as opposed to being lived by choice, and while that is probably the case more often than not, such a viewpoint negates the heavy upside of a lack of lasting relaitonships or personal ambition. Basically, a true loser has very little left to lose, so their actions are largely devoid of consequence. Thusly, Frank says what he wants, dresses like he wants, wears ironic hats and watches TV marathons of whatever he wants, and worries little about the effects of doing so. Even better, he manages to do this all while being respectfully employed, as his enviable position as a TGS with Tracy Jordan staff writer is largely dependent on his caustic and borderline-narcissistic sense of self. He might not get laid much, he may not be invited to many Bar Mitzvahs, and he may not see a second’s worth of daylight more than absolutely necessary, but he is happy and secure in his own skin. And for that, Frank Rossitano is an inspiration.

Classic Loser Moment: When a fully-bearded, haggard-looking Frank emerges from three months straight of playing Tracy’s new porn video game (Goregasm) and mistakenly claims that he played it for an hour and it was OK.

#17.

Andy Botwin, Weeds

Played By: Justin Kirk

Born to Lose: Andy is something close to the Siddhartha of losers, attempting a wide and impressive array of shady and unsuccessful career paths over the course of his four seasons thusfar on Weeds. He’s been a drug dealer (obviously), a porn star, a disgraced soldier, an immigrant coyote and just an all-around layabout so far, all with a cynically jovial gusto that no other character currently brings to TV. He doesn’t quite have the loser joie de vivre of Frank, but he appears to have reached an understanding of sorts with the world–he knows he will likely never be one of its chosen sons, and that’s cool with him, as long as he can still smoke all day, avoid any sort of manual labor and occasionally get to fuck hot Israeli chicks. But unlike Frank’s wholly self-centered existence, Andy does take great satisfaction in acting as an extremely warped father figure to Shane and Silas, his dead brother’s kids, giving them advice like “It took me years to realize that slightly deformed chicks were the way to go. I dated this one girl with a midget arm…amazing in the sack! Plus, when she held my dick in her hand, it looked huge.”

Partner in Loserdom: Kat Wheeler, Andy’s nutty free-spirit of an ex-girlfriend, played by Zooey Deschanel. Hanging around at the end of season two and beginning of season three, she pisses off and then hooks up with Andy a couple times, then flies the coop with Shane in tow, eventually letting abandoning him at a rest stop with the immortal words: “We’ll meet again. I’ll be older, but I’ll still be hot. And you’ll be older and you’ll still be the same smart, wise, gentle soul you are now, but you’ll be taller. And I think that you’re gonna do some really interesting things with your facial hair. I just see it. Okay Sweetie? Heart hug, heart hug. ”

#16.

Carl Brutanananadilewski, Aqua Teen Hunger Force

Voiced By: Dave Willis

Born to Lose: Carl is the Adult Swim version of Bill Dauterive–similarly besot by weight gain, baldness and a nasty predilection towards living in the past, but also far more vile, mean-spirited and un-self-conscious (and with a far bigger appreciation for late-70s arena rock). Carl’s a loser by nature, sure, marginally employed, semingly friendless, and often admitting to a lifetime devoid of consensual sex where money was not involved. But it also runs deeper than that, as life in general goes out of its way to force losing on him at every possible opportunity–in nearly every episode of Aqua Teen Hunger Force, Carl has his house burned down, car destroyed, TV possessed, or is just straight up killed as a result of the Aqua Teens’ shenanigans. Sometimes he gets mad about it, but as the series progresses, he takes his enforced misery more and more in stride (or at the very least, no longer seems surprised by it). Whenever some smart kid gets pushed around by bullies in middle school, and he tells himself “that’s all right, in ten years I’ll be working for Microsoft while that asshole is too pereptually fucked-up to even hold a job pumping gas,” Carl is the kind of loser that he’s hoping he’ll turn into. Except without the perpetual death, maybe.

Classic Loser Quote: Carl, while drunk dialing girls from his old High School yearbook: “Normally I wouldn’t do a fat chick from the flag corps, but, uh…IT IS A NEW ERA!! Of lonelines…”

(Prev: #25-21 / Next: #15-11)

100 Years, 50 Losers: #25 – #21

#25.

Meg Griffin, Family Guy

Voiced By: Mila Kunis

Born to Lose: The thing that’s easy to forget about Meg Griffin is that she didn’t start out as self-parody. Originally, she was just what she was–a boring, stock character that you always dreaded seeing getting prominent minutes on screen. Then, somewhere along the line, a remarkable thing happened–not only did Seth McFarlane and the Family Guy crew realize that nobody liked Meg, they decided to let the rest of the show’s cast voice the audience’s frustrations by deriding her at just about every possible opportunity. At first it started somewhat gentle–the family was completely oblivious to Meg and her problems, but that wasn’t entirely dissimilar to the way Lisa was ignored on The Simpsons. Over the years, though, it just got crueller and crueller, until it wasn’t uncommon to see Peter dunk Meg’s head in her cereal bowl for no apparent reason, at which point Meg no longer got any plots of her own that weren’t explicitly about how much everyone hated her. Unsurprisingly, the schtick wore thin fairly quickly, but for a while, it was legitimately refreshing to see a show that echoed its fans’ sentiments so honestly.

Real-Life Retribution: Well, Meg happens to be voiced by this person:

#24.

Jess Mariano, Gilmore Girls

Played By: Milo Ventimiglia

Born to Lose: Jess was that all-too-rare breed of teenage TV character–the loser heartthrob. And I don’t mean an accidental heartthrob the way our next entry ended up being–I mean a genuinely brooding, absolutley gorgeous heartbreaker. Rory was set up with All-American Good Guy Dean for much of the show’s early run, but when class-cutting, family-abandoned Jess was introduced, it was only a matter of time–he was kind of a jerk, sure, but he was tempestuous, he was well-read, he wore a leather jacket and will you look at those eyes. Rory couldn’t resist herself, and eventually broke it off with Dean to be with him. Yes, Jess did us all proud–for a little while, at least. Eventually Jess took his bad boy image a little too much to heart, and believed himself too Wanted Dead or Alive to enjoy a nice, quiet relationship with the similarly fetching Rory in small town Stars Hollow. His jealousy gets the best of him, he flunks his senior year, he splits for California, and Rory loses her virginity to a now-married Dean a year or two later. Hayden Panettiere’s not a bad silver medal, but I always wished that Jess could’ve worked it out with Rory somehow.

What Could Have Been: Jess’s trip to Cali was supposed to serve as a backdoor pilot for Windward Circle, his own spin-off. Love you always, Jess, but I’m not so sure you really needed a Private Practice.

#23.

Seth Cohen, The O.C.

Played By: Adam Brody

Born to Lose: It’s hard to get in touch with that part of myself that was so ridiculously wowed by Brody upon first viewing The O.C. in that magical summer of 2003. Not only did his performance become so ingrained in our pop culture that we began to take him for granted, but he got pretty grating pretty quickly–like the rest of the show, two seasons was about all he had in the tank. But it’s also important to remember that when The O.C. started, no one could’ve guessed that show creator Josh Schwartz had a hidden agenda to make the show a perpetual shill for indie culture–we thought it was just going to be a ridiculous, sensationalized teen drama like we’d seen dozens of times before. And from the first episode at least, that’s exactly what it was–the parties, the fights, the rampant drinking and drug use, and the horrific romantic sub-plots all made it look like the show was shooting for 90211 status. Except for Seth. He didn’t look like the rest of the cast, he didn’t act like the rest of the cast, and he talked absolutely nothing like the rest of the cast–he seemed like he had wandered in from the cast of a Judd Apatow show. Before all the comic book references, before the indie band namedrops, he was the reason viewers like me stuck around the show–he promised that there was something more from it still to come. And for at least two glorious, glorious seasons, he–and the show–did not disappoint.

Personal Loser Bond:Call it fate if you’d like, but when I had to make up a fake name for myself when I was in middle school–a good three or four years before the genesis of The O.C.–I would use Seth Cohen. Dunno, always liked that name.

#22.

Ziggy Sobotka, The Wire

Played By: James Ransone

Born to Lose: Oh, Ziggy–will you ever win? Season two of The Wire was by far the most polarizing of the show’s seasons, but chances are, if you were pro, a lot of it had to do with Ziggy, one of the most loveably despicable losers in TV history. From the moment the shrill-voiced, mousy-looking Ziggy first whipped his dick out in the season premiere, you knew things were not going to end well with the ne’er do well, who was perpetually getting in over his head with crimes he wasn’t clever enough to pull off, money he wasn’t smart enough to handle, and dudes he wasn’t nearly bad enough to keep up with. Still, loud and obnoxious as he was, you still had to feel for the guy–he was so perpetually out-classed at every turn in his day-to-day life that it was nearly impossible to begrudge him his overambitious nature. And at the very least, he possessed an enviable sort of joie de vivre that came a short way to justifying his life of impulsive decisions and poor foresight. My all-time favorite Ziggy quote came from “All Prologue,” when, rich from a recent score, he’s buying everyone at the bar drinks and lighting cigarettes with $20 bills. Upon criticism from his more responsible cousin Nicky, he responds “When I’m flush, I’m flush. We ain’t gonna live forever, right?”

Ultimate Low Point: Almost impossible to choose for a man with as many low points as Zig, but it’s still gotta be the duck. Some heartbreaking shit right there.

#21.

Lindsay/Nelly Bluth Funke, Arrested Development

Played By: Portia de Rossi

Born to Lose: Stick a wrench in her, she’s done. Credit the Arrested Development for not falling into the trap of making Lindsay your typical dumb hot chick who gets by on her ability to seduce rich, successful men–instead, Lindsay’s your typical dumb hot chick with no perceivable abilities whatsoever beyond basic self-preservation. A spoiled rich girl with Daddy issues, Lindsay had the bad luck of marrying a similarly useless (and most likely homosexual) theater wannabe, and has no choice but to stick around her dysfunctional family in the hopes that someone will take pity on her and let her steal the company credit card. And as with Sweet Dee on Sunny (who, as many have noted, looks and acts like a strung-out version of Lindsay), she isn’t any more moral or sympathetic than any of her male counterparts–she’s just a loser, like the rest of ’em. And so she gets as much shit as the rest of ’em, including a final run in the show’s third season that ends with her finding out she was adopted, unsuccessfully hitting on her brother (and being unsuccessfully hit on by her other brother), and eventually getting sold by her mother to her birth father.

All’s Well That Ends Well: Somewhat ironically, Portia herself came out of the closet around the end of the show’s run, and is currently married to the world’s most popular lesbian, Ellen DeGeneres. Meanwhile, David Cross is supposedly dating one of the Sisterhood of the Traveling Pants, amazingly enough.

(Prev: #30-26 / Next: #20 – 16)

100 Years, 50 Losers: #30 – #26

#30.

Samuel “Screech” Powers, Saved By the Bell

Played By: Dustin Diamond

Born to Lose: For those of a certain generation, Screech will forever be the go-to when contemplating the mental image of High School loserdom. He was smart but not necessarily intelligent, extremely outgoing but without any sort of finesse, and a member of the popular crowd without actually being popular. More importantly, he looked like the picture above–a Jewish, acne-ridden schlub without the wit of Woody Allen or even the self-awareness of Seth Rogen. This was what young losers of the early 90s believed they had to look forward to upon reaching high school, and to be fair, for a show of its time, Screech wasn’t that far off. Was there any doubt that this guy was going to grow up to do porn and dress like Kevin Federline?

Too Close for Comfort: Sez Wikipedia: “Diamond was three years younger than most of the cast of Saved by the Bell. Because of the age and religious differences, he was never very close to any of the other teenage actors on the show. He said that while the other teenage actors went out together and got along, he basically did his own thing.” The article says that he did get along pretty well with the guys who played Principal Belding and the maintenance dude from Good Morning, Miss Bliss. Aw, Samuel…

#29.

George O’Malley, Grey’s Anatomy

Played By: T.K. Knight

Born to Lose: It’s hard to remember now, but there was a time when George O’Malley was pretty much the Lloyd Dobbler of prime-time medical melodrama. Poorly dressed, shaggy-haired, looking and acting younger than the rest of the interns, it’s no surprise George never earned a McNickname. Instead, he got stuck in the friendzoniest of friend zones with roommate Meredith Grey while she fell in and out of a relationship with the dashing Dr. Shepherd, and caught syphilis from his worst enemy, the even dashing-er Alex Karev (via their mutually shared girlfriend). O’Malley eventually hooked up with the supremely annoying Callie Torres, cut his hair, and became as boring as the rest of the Seattle Grace staff (while coming off as TV’s biggest wet blanket off-screen by inadvertently running co-star Isiah Washington off the show). Still, George was what made those first two seasons compelling, which in retrospect was a hell of an accomplishment.

Ultimate Low Point: In S2, George actually finally manages to bed Meredith, but she can’t stop crying while they’re having sex. An impressively unwatchable moment from a show whose idea of real human drama was to have the doctors treat a patient that had a ticking timebomb inside of their stomach.

#28.

Non-Alltel Cell-Phone Service Providers, Alltel Commercials

Played By: Matthew Brent, Scott Halberstadt, Ian Gould, Michael Busch/Adam Herschman

Born to Lose: The non-Chad cell-phone representatives of the world are far from the most successful of business paragons, being trumped at every turn by those with more pragmatic (and less inhuman) service strategems. Nore are they necessarily sympathetic characters, trying to cheat trusting customers out of lower rates and more minutes at just about every possible opportunity, and sniping at those who wish to do right by the constituents. Still, when the other side is represented by a do-gooder as despicable as Chad–with his gelled up hair, shiny outfits, Svengali-esque powers of persuasion and exceedingly villainous name, is it really any mystery who I’m rooting for, against all odds, to come out victorious in these ads? Don’t worry, guys–some day you’ll tempt the wizard back to your side with promises of orbs or powders or rare Magic: The Gathering sets, and then Chad will rue the day he first decided to let kids share his lemonade stand.

Damned With Faint Wikipedia Praise: Of AT&T doppleganger Scott Halberstadt: “In most appearances in shows he is acting as the geek or nerd.”

#27.

Bill Haverchuck, Freaks and Geeks

Played By: Martin Starr

Born to Lose: Needless to say, there was no shortage of loser characters to go around on Freaks and Geeks–of just about all stripes, in fact. Really, though, when you get down to them, only one of them was particularly likeable, and that was Bill Haverchuck. Mostly, that’s because unlike hissimpering geek friends and the self-stylized freaks found elsewhere on the show, Bill was perfectly comfortable in his own skin. He didn’t question his place in the world, he didn’t try to improve his station–he was a nerd, and he didn’t hide or sugarcoat it. So he dressed up like The Bionic Woman for Halloween, feuded with his gym teacher, and obsessively followed the plot of Dallas, never doubting or apologizing for his life choices. He had a self-confidence that made you sure that he’d turn out pretty OK, and based on Martin Starr’s performance (essentially as himself) in Knocked Up, he probably would’ve been pretty tight with one of my friends on the Ultimate Frisbee team at Hampshire. To be fair, though, it was John Francis Daley who had the post-F&G role of a lifetime as the silent trainee in the criminally underrated Waiting.

Classic Loser Quote: “Remember that time in civics when I had to fart, and it came out, well, a poop? And I had to flush my undies down the toilet? Do you think I wanted to tell you that?”

#26.

Cliff Clavin and Norm Peterson, Cheers

Played By: John Ratzenberger and George Wendt

Born to Lose: Sometimes you wanna go where everybody knows your name, because in your day to day life, you’re such an unbelievable nobody that even expecting someone to know what to refer to you as is a little but too much to ask. When you’re a teenage loser, you go to your room and dream about the day when you’re old or independent enough to make your own way in the world. When you’re an adult loser, you go to a bar, drink yourself to oblivion and wonder why the fuck that day hasn’t come just yet. Of course if you’re lucky enough, you at least have some other like-minded folk to do it with, and at the very least, Cliff and Norm–two middle-aged men with unexceptional employment, unfortunate unlucky streaks and perpetual woman issues (romantic and maternal)–always had each other, and had at least one place in the world where life was always OK. Cheers might not’ve necessarily romanticized the adult loser persona, but it definitely gave it a sort of quiet dignity, showing that there were enough of them out there that if you were fortunate enough to find each other, there was enough to constitute a family.

Moment of Triumph / Ultimate Low Point: In one of the few episodes of this show that I still vividly remember, for obvious reasons, Cliff goes on Jeopardy!, catches a dream board and cleans up, but as Norm correctly predicts from the audience, blows it all on an incorrect Final Jeopardy guess. Hey, they don’t call ’em losers for nothing…

(Prev: #35-31 / Next: #25-21)