Bar mitzvahs, older women, and the Apple TV+ streaming wars: Welcome to Cooper Raiff’s Hollywood

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Cooper Raiff had big plans for his breakthrough international press tour. The 25-year-old Texas-raised multihyphenate (writer/director/actor/editor/producer) is currently riding a wave of buzz for his second feature, Cha Cha Real Smooth, a rom-com that follows aimless college graduate Andrew (Raiff) as he finds love with an older woman (Dakota Johnson) while working New Jersey’s bar-mitzvah party circuit. After premiering at this past January’s Sundance Film Festival, Cha Cha was picked up for a cool US$15-million by Apple TV+, cementing Raiff’s enlistment in the high-priced streaming wars.

But just as Raiff was heading to Toronto for Cha Cha’s Canadian premiere, a passport snafu left him temporarily stuck in New York – a “pretty big bummer” of a situation that also sounds like something Andrew himself might get mixed up in. Which is all part of Raiff’s filmmaking charm: There seems to be only a thin line separating the filmmaker from his creations, including Alex, the lovesick college student that Raiff played in his first film, the sweet-despite-its-name 2020 dramedy, S#!%house.

Ahead of Cha Cha Real Smooth’s streaming premiere this weekend on Apple TV+, The Globe and Mail spoke with Raiff (virtually) about growing up with the whole indie-film world watching.

How much of you is there in Cha Cha’s Andrew? Or for that matter, S#!%house’s Alex?

A lot. With Alex, it was my feelings embedded in a person. And with Andrew, I share a lot of his mommy issues. I find it more comfortable to be with another person than to spend time in a room by myself. With Andrew, it was someone who is 22 years old, a time when you can really figure out who you are, but he’s a person who desperately wants to be 32.

Andrew wants to be older, and your films have the do-it-yourself confidence of someone much older than you are, too. Do you feel like you’re trying to constantly get ahead of your own age?

No, because when I’m 32 I’ll want to be 32 forever. It’s not about not being present, but not being afraid of feeling. With Cha Cha, I was trying to get to a place of making that age, your 20s, joyful. The original idea was just Dakota’s character, the mother of a young disabled daughter. But then I thought it would be nice to show this 22-year-old about to enter this phase that her character just didn’t get because she had her child so young. So they’re helping each other get strong.

The concept of home is central to these films. In your first film, Alex is reticent about leaving home for college. In Cha Cha, Andrew is forced to return home after college. You’re now making your temporary home in Los Angeles. Do you miss your own nest?

I wrote the script for Cha Cha about two months after I’d gone home during COVID. And going home after leaving is this specific feeling of having to relate in entirely different new ways that are not comfortable at all. I never wanted to do a scene that was on-the-nose with Andrew and his mom. My mom and I, we have a complicated history, but we don’t go back in time ever. We keep the conversations right here, in the moment. And that’s what Andrew and his mom do in Cha Cha. I just want to say, though, that I love my mom.

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I’ll just say that I’m glad that there’s finally a movie about the bar-mitzvah circuit. But you aren’t Jewish ...

The original idea I had was to just find a way for this 22-year-old guy and 32-year-old mother to keep coming into contact with each other. The bar-mitzvah idea was a bit silly, but I did have a lot of experience. I went to a small school in Dallas that was heavily Jewish, from kindergarten to 12th grade. That didn’t mean anything until I walked into my first synagogue service, which I went to for every Saturday in seventh grade for all these bar and bat mitzvahs. I also dated a girl in high school for three years who was Jewish. Which meant a lot of Shabbat dinners where I desperately wished I knew the prayers.

The last time that Apple TV+ bought a movie at Sundance was 2021′s CODA, which went on to win Best Picture. Do you feel any pressure in being their next big acquisition?

I really hope that people don’t watch this movie thinking about CODA winning an Oscar. People can realize that this movie is called Cha Cha Real Smooth and think of it as the summer movie starring Dakota Johnson. I haven’t put any pressure on myself. But it is hard not to think about, “Oh God, don’t watch it through that lens, please.”

This interview has been condensed and edited

Cha Cha Real Smooth is now streaming on Apple TV+

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