Voiced By: Adam Welsh
Born to Lose: Beavis and Butthead weren’t exactly kings of the hill themselves, but they were still at least one step higher in the pecking order than poor little Stewart. A nice, mild-mannered mama’s boy, Stewart for some reason made the questionable decision to make hanging out with B&B his greatest social aspiration, a judgement call which resulted all too often in him either getting in trouble when B&B framed him for their misdeeds or getting his ass kicked by associaton. If we could’ve seen him grow up for a few years, no doubt Stewart would wisen enough to realize how little B&B cared for him, make friends with one of his science teachers and run out the High School clock in a life of dignified loneliness before getting into a good school and learning that the only thing better than watching The X-Files at 3 AM by yourself is doing so stoned with a bunch of friends. Too bad the show was animated, I guess.
Little Known Fact: Stewart’s legendary Winger t-shirt–permanently sealing the band’s metal punchline status–was created out of vindication. Had Kip Winger not so incensed Mike Judge by bitching about the boys’ cruel disregarding of his band’s videos, “Miles Away” and “Headed for a Heartbreak” might at least currently be karaoke perennials. As is, I think we need at least another 20 years.
Played By: Peri Gilpin
Born to Lose: A relatively smart, sneakily attractive and comparatively earthy working girl, Roz might’ve been an unqualified winner if she had better luck (or taste) in dudes. Forever harboring a penchant for ex-frat boys, Roz was perpetually in and out of bad relationships, including glorious scumbag co-worker Bulldog, a college student that ends up knocking her up, and on at least one regrettable occasion, ol’ bossman Frasier himself. Not that Frasier and Niles always had impeccable taste either, as the latter especially flirted with romantic loserdom over the course of the show, but somehow it was always Roz who ended up on the losing end of the bad jokes. She ends up relatively successful as a station manager and single mom, but while everyone else on the show seemed to couple off by the end, Mr. Right never did quite show up for Roz. Maybe she ended up giving Noel a chance after getting drunk on her 50th birthday or something.
What We Almost Lost: Before she went on to frolic around a fountain and listen to The Rembrandts, Lisa Kudrow was famously groomed for the role of Roz. Ironically, the actress who would go on to define aggressively quirky sitcom acting in the 90s was cut from the show because Grammar “overpowered her” in scenes together.
Played By: Jorge Garcia
Born to Lose: It wasn’t just that Hurley was a loser by nature–nature made damn sure at every possible turn that Hurley never actually won. With a ~400 lb gait, a slacker’s demeanor and Cheech Marin as a father, he was never going to be much of a go-getter, but even winning the lottery turned out to be nothing but a huge curse for Hurley. Maybe he thought he had escaped his bad luck on the Island, making some friends, going on some nifty missions and even getting a little girlfriend for a little while, but there’s no escaping The Numbers, and not only does his belle ends up getting murdered by one of his friends, his potentially automatic weight loss is offset by bountiful rations of food getting dropped on the island (DAMMIT!). And though we don’t know why yet, the fact that he ends up back in the mental hospital, haunted by his dead islandmates, probably doesn’t bode too well for Hurley’s fortune turning around any time soon.
Moment of Triumph: In the proud tradition of fat guys everywhere, Hurley turns out to be a master ping-pong player, schooling a predictably cocky Sawyer in a Season Three episode. Too bad there are no bowling alleys or bar trivia contests on the island.
Voiced By: Alvaro J. Gonzalez
Born to Lose: “Hey Daria.” God bless the 90s for allowing a show where a character like Trent could not only avoid being comic relief, but could actually be a veritable pixilated heartthrob–girl losers wanted him, and guy losers wanted to be him. A post-adolescent with no considerable aspirations beyond singing and playing guitar in his band Myystic Spyyral (but they’re thinking about changing the name), Trent was the animated poster boy for the soy un perdido decade. He was scruffy, he was rail-thin, and he was laid back to the point of near-sonnambulism. Unlike live-action slackers-in-arms like Jordan Catalano or Daniel DeSario, though, Trent was actually a pretty cool guy, not nearly as emotionally inept as the former or as insiduously manipulative as the latter. He was just sapping up the glory of those last few years of youthful aimlessness before 25 squelched his passion and he ended up as a “townie doing Doors covers.”
Legacy of Loserdom: The similarly guitar-fixated, van-driving, lax-demeanored (not to mention exceptionally more talented) Dwayne from Home Movies owes much to Trent’s shining example. He’d merit a place on the list himself were he not amidst such stiff competition from his co-stars.
Played By: Gabrielle Carteris
Born to Lose: Oh, Andrea. There’s not a single character on this list less enjoyable to watch than Andrea Zuckerman–she was shrill, she was boring, she was an impediment to just about everything good that 90210 had going for it. But it would be heavily remiss of me to not at least pay some low-seeded respect to the first loser girl of the teen soap genre, a tricky archetype that almost 20 years later, has arguably still yet to be perfected. And oh boy, was Andrea a loser–stressing about safe sex while remaining a virgin herself, taking her high school newspaper far too seriously, and harboring a (mostly) unreciprocated infatuation with co-writer (and in many ways, co-loser) Brandon. But rather than being cute and endearing for her dorkiness, Andrea was just kind of a wet blanket, looking and acting like she should be handing out tardy slips or Scarlet Letter lesson plans instead of pretending like she was one of the gang–unsurprising, given that in real life she was about a decade older than many of her co-stars.
Breaking the Cycle: Ironically, Andrea would appear to reverse-age as the show went on and she started dressing and getting into soapy entanglements more like the rest of the cast, evolving her character from irritating to redundant. Whether this was an upgrade is (possibly) a subject of great debate.