At age 23, in 2020, Greenhill School alumnus Cooper Raiff won the top prize at the SXSW Film Festival on a movie called Shithouse.

It was all almost too easy. He had made an early version of the movie with his college buddies and tweeted a link to one of the famous Duplass brothers, Jay (the one in Transparent), who loved it and helped Raiff launch a career that is going very very well.

It was then that I first heard of Raiff, from his uncle Jeff Wade, who you may know as one half of the Ben and Skin radio show.

Shithouse, a coming of age about a young adult (played by Raiff himself) who calls his mom crying from college (among other plot lines), made me weepy and hit me close to home. It also included a few nods to home, which is endearing if you’re from Preston Hollow or attended Greenhill — for example, in the film he wears two different Greenhill School hoodies (one reads Greenhill Wolves, which is not actually the school’s mascot, which the young filmmaker explains in this Slant interview with a grad from a rival school) and also dons a Mavs “The Time is Now” T.

We all felt a little sorry for Cooper Raiff in one respect, because that year SXSW was basically a publicity bust due to a national health crisis.

But there is no need to feel sorry for him now. The 2015 Greenhill grad is on a Hollywood “hot streak,” They say.

Apple TV just purchased his latest feature film, Cha Cha Real Smooth, for $15 million.

That marks the highest purchase yet for this year’s virtual Sundance market.

In Cha Cha, Raiff plays a directionless twenty-something recent grad in New Jersey who gets in over his head in a relationship with a young mother (played by Dakota Johnson) and her autistic teenage daughter as he works a job as a “party starter” at bar and bat mitzvahs. His mom’s played by Leslie Mann, and his day job (the parties being a side hustle) is at a food-court joint called Meat Sticks.

Critics reacting to Cha Cha are comparing Cooper Raiff’s arrival on the scene to that of Steve Carell, Seth Rogen, Emma Stone and Adam Sandler.


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