The Dress Up Gang: A Criminally Underrated Web Series

I wasn’t looking for laughs when I clicked onto The Dress Up Gang’s Vimeo channel, but boy, did I find them.

My entry point into this criminally underrated series was a video simply titled ‘Toothpick.’ In it, the subtly brilliant Donny is the focus of his friend group’s concern (and ultimate intervention) when he won’t give up his ‘arrogant’ toothpick habit. The performances were understated and the one-liners were brilliant. And so, I clicked on their next episode ‘Cute House.’

When I say this seven-minute episode is genius, I mean it. The episode starts with three guys discovering a ‘cute’ house, and ends in a men’s support group addressing the generational trauma of Frankie, who’s reeling from a childhood exchange with his tia where she refused to call him cute. (Highlights include when Kirk, a white man who’s play-acting the role of his tia screams, ‘What’d you say to me, mijo?!’) The whole thing’s cute as shit and it made me wonder—why have I never heard of The Dress Up Gang before?

The answer to that is perhaps due to the web series’ hot-cold history with TV network TBS, who ordered 10 half-hour episodes of The Dress Up Gang off the strength of their original web series and pilot. But after a merger with AT&T and Time Warner that saw management reshuffling, TBS cancelled the show as it was in the final stages of post-production. Bummer.

So, the show’s creator decided to upload the series to the internet themselves. But wait! The flipping flopping continued, and in May of 2020, TBS decided to reverse their decision and stream the series after all. There’s a whole bank of their episodes on both YouTube and Vimeo though, so TBS or no TBS, you’ve got a whole archive to dig through.

Like the best understated comedies, the plot lines don’t veer into the outrageous and they’re not longer than they need to be. Episode storylines include a friend who’s been in the pool for two hours and six beers and is suspected of having peed in the pool, an abusive fiddle leaf fig owner who gets called out at the park, a friend who’s only pretending to take shots with the boys, and the search for a friend on a bad mushie trip.

Going off my own experience, it’s never too late to join The Dress Up Gang: check out their stuff on Vimeo or YouTube.  

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