Cooper Raiff Debut Won SXSW & His ‘Cha Cha Real Smooth’ Is Sundance Buzz Title Now: Will Covid Ever Allow Him To See His Work In A Crowded Theater?

Mike Fleming Jr

EXCLUSIVE: Cooper Raiff can’t seem to catch a break from Covid. A hyphenate who comes into Sundance with one of the buzziest acquisitions titles in Cha Cha Real Smooth, Raiff is coming off the debut Shithouse — it’s more thoughtful than it sounds — that won the Grand Jury Prize at 2020 SXSW. Unfortunately, it was also the first major festival forced to cancel in-person events by Austin when Covid exploded. Raiff has made another charming confused young man comes of age film that he wrote, directed, produced and starred in. And now has run smack into Covid Delta’s sequel, Omicron. Which means he’ll keep intact his festival streak of being unable to experience his film playing in a crowded theater, a disadvantage since he makes crowd-pleasing films. The film, which stars Raiff, Dakota Johnson, Leslie Mann, Brad Garrett, Vanessa Burghardt and Evan Assante, makes its virtual Sundance debut tomorrow. The hope is that by the time the film gets released, Raiff’s work can be discovered in a theater. “Cooper’s magic is that his vision remained consistent, only deeper because of his interactions with the actors,” said producer Erik Feig, whose Picturestart co-financed the film with Endeavor Content. “Cooper is a true humanist fully of empathy that is infused in every frame of this film.”

DEADLINE: Your second film gets accepted into a major film festival after your first won the SXSW prize, and once again, Covid rears its ugly head. How are you taking this?

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COOPER RAIFF: Well, I’m sad. I was really over the moon about Sundance. It was a big goal for us, when my producer Ro Donnelly and I were making Cha Cha, that this was the perfect film to see in a theater at the film festival. So it’s a major bummer, to still not know what that experience feels like.

. - Credit: Courtesy Cooper Raiff
. - Credit: Courtesy Cooper Raiff

Courtesy Cooper Raiff

DEADLINE: Despite the SXSW setback, how did the first movie play out for you?

RAIFF: Great. Everything on that first movie felt like such luck. It was really hard to feel anything negative, because it felt like everything was going that movie’s way. Honestly, I just thought it would be my friends and my family seeing that movie. When IFC bought it, it felt great, all the way through.

DEADLINE: You’ve taken a real jump with Cha Cha, mining a more sophisticated and emotional storyline. There aren’t that many filmmakers who handle as many jobs on their early films as you do. Do you have a North Star, a filmmaker or film that sparked you to mine this relationship drama with comedic overtones?

RAIFF: The Duplass Brothers, for sure. I’m close with Jay, who helped me make Shithouse. Growing up, they were the guys; I watched all their movies and fell deeply in love with everything they were doing. I just watched Jay’s pilot, Somebody Somewhere for HBO. I flew to LA yesterday, watched it on the plane, and I bought wi-fi just so I could tell him how amazing it was. He didn’t write that one, but everything he touches feels like magic to me. He will always be the guy I get fanboy about. My real North Star is, I want to care so deeply about what I’m working on because this is so much work and I really want to be super in love with all the characters I’m writing. I want people to fall in love with them. Someone who does that is Greta Gerwig. Everything I watch from her, I can feel that she adores everyone on camera. She’s trying to make something appealing but when you go deeper, what she’s really doing is making you love the characters as she does.

DEADLINE: How tough was it to pull together Cha Cha Real Smooth, made in a moment when every production was more expensive because of Covid protocols and completion bonds and things like that?

RAIFF: Making any movie is a little miracle. Everyone I’ve worked with on this movie was so passionate. It had its bumps and was a rollercoaster, but it didn’t feel like I was getting pushback, ever. Covid sucks, and making movies with masks on is hard and it’s a gigantic cost. But it was nice to be in that with people like my producer Ro Donnelly; she fought the entire time for this movie to get made sooner than later. I never felt like I was by myself on an island. So many people wanted to see this happen.

DEADLINE: Even though it loomed over Shithouse and Cha Cha Real Smooth with their festival premieres, were you able to make the film without being shut down?

RAIFF: We didn’t shut down, at all. We got out totally alive. No one got Covid on set, which felt like a miracle. I joked the other day in an interview that maybe the third time will be the charm, because both my first two experiences didn’t turn out well with an in-person festival, and I got mad at myself. Because it feels like a miracle when you get a film made, and it might never happen again. Don’t you want to take a moment, a beat, and see the fruits of your labor? It’s easy to joke, but having made a movie during Covid and having it turn out watchable, feels like an accomplishment.

DEADLINE: Covid has hovered over the premieres of your two films. Have you personally been able to avoid a Covid bout?

RAIFF: Crazily, yes. I haven’t gotten it, yet.

DEADLINE: So the hard part is not experiencing that moment where you see your film play Eccles, and you can feel when they are reacting to what you and your cast worked so hard to bring to life. When will you be able to experience this, in a room with people?

RAIFF: Hopefully, somebody, but not this week. They’re doing a Q&A after the screening Sunday, and Dakota, Vanessa and I are getting all the tests to make sure we are safe, but we’re going to be in a room together to watch the movie and do the Q&A together. That will be nice. Vanessa plays Lola in the film. Hopefully it will be other festivals, later in the year

DEADLINE: Your movie has as much buzz as any acquisition title here, and this is a game for optimists. Some have said that by the time these movies are released, maybe Omicron will have run its course and moviegoers will be more comfortable going back to theaters.

RAIFF: I am so looking forward to that. But it’s hard to complain, because I’m getting to make movies and that’s what it’s about. Making something that means something, with people that mean a lot to me. But that experience of seeing my movie with a crowd, that will be super badass.

DEADLINE: You seem to have arrived to this place quickly. How did you get here?

RAIFF: I wasn’t making movies as a kid. I loved movies, but was into acting and theater in high school. My senior year, when everyone was talking about college, I decided I wanted to write, in college. I wrote a play my senior year and acted in it. That was the first time I really felt like I enjoyed making something, and being the author of it. When I got to college, I started writing a lot and realized how hard it was to get important people to read any of it. So I took the Duplass Brothers path; just make it, because the cavalry isn’t coming. So I made a very small movie and that’s what I sent to Jay. We met and the rest is history.

DEADLINE: Is The Trashers up next for you?

RAIFF: Yes, that’s my next movie I’ll work on. It’s with 30West and Tom McNulty and Andrew Morrison, and we’re now in the middle of trying to cast it.

DEADLINE: It’s your first non-fiction film, about a Connecticut-based businessman who bought the city’s minor-league hockey team in 2004 and assigned his teenage son to run it. While the youth turned the team around, it ended when his father was arrested on 72 criminal charges.

RAIFF: It was the most exciting thing, to make a movie about real subjects that have nothing to do with my life. This is one I’m not going to act in and it feels very freeing, being able to just focus on directing and doing right by the story. I still have to find a personal way in, and that is the father-son story. I haven’t made a relationship about that and I’m antsy to do that. This relationship is based on a hockey bond. This was their bond for so long and then as he’s graduating high school, they realize, this big factor in our relationship is about to be gone. He’s not going to be able to play hockey after this. It’s something I had with my dad, where you go, what are we going to do when we don’t have the sports to bond over? And then his dad goes and buys him a hockey team, because he doesn’t want that bond to be over. It’s an emotional story with a huge heart and I found a very personal way into it. It will be a relationship story, but a bit larger than life and crazy.

DEADLINE: What will make this a successful, virtual Sundance for you?

RAIFF: It will be Vanessa…

DEADLINE: Who plays the autistic daughter of Domino (Dakota Johnson)…

RAIFF: I want her to love it. If she does love it, and she enjoys doing the press, that’s going to make me feel very animated. And I will be very excited about that.

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