The embarrassing beginning: nine comedians’ roles they’d probably like to forget

As anyone in show business can attest to, the entertainment industry can be horribly cutthroat and demoralizing. Everyone has to pay their dues, do their time, and otherwise work their way from relatively uninspiring, embarrassing, or generically shitty roles and jobs. Of course, any occupation requires working up from the bottom, but the entertainment industry makes that journey a public one.

And, sometimes, well-established actors have a dry spell and have little choice but to take a role that they might prefer not to, lest they fade into obscurity. Aside from the occasional “Where Are They Now?” cable TV special, of course. The volatility of the industry, however, is good for all of us on the sidelines. We can take heart in – and giggle at – the fact that some incredibly successful comics and actors started with some ridiculous roles at the dawn of their careers. Or are forced into ridiculous roles in the middle or end of their careers. Hey, everyone’s gotta eat, right? So, without further ado, we present to you a compendium of 10 comics’ embarrassing roles.

Robert Kelly, The Job (2001)
Eleven years ago, we were lucky enough to be graced with a comedy-crime TV series called The Job, created by and starring Denis Leary. Also appearing was a very young and suave Robert Kelly playing a dude named Lou.

Robert Kelly on WhoSay

Garry Shandling, Mother Goose Rock ‘n Rhyme (1990)
Holy shit, this movie is still one of my favorites ever. My brother and I watched it all the time as kids, knowing nothing of the insanely famous cast. In what other fiction movie would you ever see, on the same cast, Little Richard, Cyndi Lauper, Teri Garr, Art Garfunkel, Shelley Duvall, Woody Harrelson, Bobby Brown, ZZ Top (all of them!), Brian Setzer, Paul Simon, Jean Stapleton, Katey Sagal, and more? That’s what I thought. That cast also includes comic legend Garry Shandling as a blue-haired Jack, of Jack and Jill fame. He bickers incessantly with Jill and they inevitably fail to fetch a pail of water. Surprise of the century. Check it out at 3:42, or watch from the beginning to see Howie Mandel portray Humpty Dumpty.

Chris Hardwick, Singled Out (1995)
My introduction to MTV – and, by extension, Chris Hardwick, head of the lovely Nerdist podcast – was in watching the weirdly addicting game show called Singled Out. If you weren’t lucky enough to see this on the air, the premise basically has a single contestant narrowing down a pool of 50 eligible bachelors (or bachelorettes) by selecting various generic qualities they’d like, and eventually singling out a final date. Hosting the show was a long-haired Chris Hardwick, who looks totally 90s. That doesn’t stop me from having a crush on him, though.

Sarah Silverman, Star Trek Voyager (1996)
Sarah Silverman got her start in the stand-up circuit at a young age, but also found the occasional bit part on TV programs – and not just comedies. Here she is driving a VW bus in an action-packed episode of Star Trek Voyager. Unfortunately this German-dubbed version is the best we can do. Es tut mir leid!

George Carlin, Shining Time Station (1991)
This show was a favorite in my household, thanks to my brother’s love of trains and machines. These days, though, I wonder what my parents thought when they saw George Carlin playing the decidedly not foul-mouthed Mr. Conductor, the miniature patron saint of the train station. Or what Carlin was thinking when he decided to take the role, filling in for Ringo Starr. As a side note, if you’re keeping along at home, Jason Woliner, executive producer of Human Giant and Eagleheart, appeared as a kid named Matt in 22 episodes. How far he’s come.

Jerry Seinfeld, Benson (1980)
It’s hard to imagine Jerry Seinfeld in a role that doesn’t require him to play himself. Before he landed a deal to make Seinfeld, though, he portrayed an obnoxious neighbor named Frankie in the early 80s program Benson. This clip, wonderfully enough, has Frankie telling some jokes. Benson is not impressed.

Bobcat Goldthwait, Are You Afraid Of The Dark? (1991)
If you’ve been paying attention to your TV or Facebook, you’ve probably noticed that TeenNick has started airing old school 90s Nickelodeon shows weeknights at midnight EST. Here’s hoping they start airing old episodes of the show that scared the shit out of every kid at the end of Snick, Are You Afraid Of The Dark? The show, aside from being absolutely terrifying, offered a few notorious guest stars, one of whom was Bobcat Goldthwait. Here he is playing the Sand Man – and I gotta say, it’s perfectly cast. That voice!

Dave Chappelle and Jim Breuer, Home Improvement (1991)
Before the dynamic duo of Chappelle and Breuer bestowed us with the ultimate stoner movie Half Baked, they both appeared in an episode of Home Improvement as dudes who always get in trouble with their girlfriends. If only we knew then what comedic gold the two would soon offer. Also, Chappelle’s fleece is wonderful.

Ricky Gervais, Seona Dancing (1980)
Technically, this last one isn’t a role, but it wouldn’t be a compilation of early career hilarity without it. Before Ricky Gervais was making waves on the comedy scene through The Office, Extras, and The Golden Globes, he met with moderate success fronting an 80s new wave music group called Seona Dancing. His hair could cut diamonds.

Carrie Andersen

In addition to writing for Laughspin, Carrie is a graduate student in Austin, Texas, where she researches popular culture, new media, music, and social movements. When not reading or writing in any official capacity, she spends her time playing the drums, watching crappy TV, and eating copious amounts of tacos and barbecue. She also blogs sporadically at

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