Jay Duplass Cast His New Biographical Movie’s Lead On A Dare

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Jay Duplass directed the new film See You When I See You, and he used a surprisingly unconventional method to find his main actor.

This movie, inspired by Adam Cayton-Holland’s memoir Tragedy Plus Time (which he also wrote and produced), tells the story of Aaron, a comedian grappling with the loss of his sister, Leah. As he struggles with PTSD, his family rallies around him, and they all begin to work through their grief as a unit.

Cooper Raiff, known for Cha Cha Real Smooth, stars in See You When I See You alongside Kaitlyn Dever (The Last of Us), David Duchovny (The X-Files), and Hope Davis (Perry Mason). Lucy Boynton (The Pale Blue Eyes) and Oscar nominee Kumail Nanjiani, who also produced the film with his wife Emily V. Gordon, round out the cast. The dramedy premiered at the 2026 Sundance Film Festival and has received mostly positive reviews, currently holding a 71% rating on Rotten Tomatoes.

To celebrate its premiere at the festival, ScreenRant‘s Ash Crossan spoke with Jay Duplass, Adam Cayton-Holland, and Cooper Raiff in our SXSW studio about See You When I See You. When discussing how Duplass and Raiff first connected, the actor remembered sending the director/producer a link to a college short film he’d posted on YouTube, challenging him with, “I bet you’ll be curious enough to watch this and see what I have to say.”

I have to admit, Raiff really got me with this one! He jokingly said it was all a brilliant marketing ploy to get me to watch his film, and honestly, it worked. I get so many tweets sent my way that I just don’t have time to watch them all. But I clicked the link he sent, and it turned out to be a full 50-minute film! We were cracking up, calling something that length a ‘schlong’ – basically a long short. But the biggest surprise? I genuinely loved it!

I often find myself intrigued within the first 10 seconds of watching something new. There was this one time I immediately thought, “Hmm, this could be something,” and called my wife in to watch. She agreed there was potential. It turned out to be a very low-budget film his girlfriend and he had made, and I was drawn to it because it felt like a raw, personal home movie that could actually work as a feature film. I wasn’t sure what it was, but I really liked the vibe.

Although Raiff has acted in several projects, including his upcoming TV series Hal & Harper, See You When I See You, directed by Duplass, is the first time he’s appeared in something he didn’t both write and direct. Raiff explained that Duplass sent him the script for the dramedy long before he was considered for the role of Aaron, hoping to get his opinion on whether or not he should take the part.

Cooper Raiff and I had a really in-depth talk about the idea that if you’re not pursuing your passions, what are you doing with your life? So when he offered me the role of Aaron, I thought, ‘If I turn this down, what else would I even be doing?’

Duplass Had A Unique Goal In Mind For Building See You When I See You’s Cast

ScreenRant asked how the team first came together, noting that the project drew heavily from Adam’s autobiography.

I wrote the screenplay, and because I’m close with Kumail Nanjiani and Emily Gordon – who were incredibly open and honest in ‘The Big Sick’ – they helped me be equally honest in my own script. Once it was ready to share, Emily suggested Jay might be a good director. Kumail passed the script to him, and he loved it right away. It was a lucky break – finding the perfect director who was enthusiastic about the project so quickly. That kind of thing doesn’t happen often, and I’m really grateful it did.

ScreenRant complimented Jay on his talent for dark comedy, comparing it to the style of the movie The Big Sick. They then asked what specifically attracted him to the script he’d been given.

Jay Duplass: I mean, the truth is I’ll direct anything.

ScreenRant: I got a script.

Adam Cayton-Holland: Put that out there.

Absolutely. I’ve always directed projects I came up with myself, so this was new territory for me. Kumail and Emily are incredibly talented and I really trust their vision. When I read the script, it immediately resonated with me – it was both funny and deeply moving. Honestly, it felt so ambitious and larger in scope than anything I’d tackled before, I wasn’t sure I knew how to direct it. But I felt strongly that I needed to be involved, that it was a really important story to tell, and it pushed me in a good way – it was a scary, but exciting, challenge.

ScreenRant asked about how the filmmakers visualized the character’s inner thoughts, praising the beautiful and creative way they were brought to life.

The film really began with Adam’s experiences and what he went through personally. I found it fascinating how he portrayed the internal events as almost physical struggles. He wrote Aaron’s inner turmoil so well, which was great because I generally avoid flashbacks – they rarely work for me. I’ve tried using them and ended up cutting them. This film is an ensemble piece, a family movie with humor, but at its core, it’s about a man overcoming PTSD, even though he doesn’t initially recognize it. We approached this journey visually, and that’s where our cinematographer, Jim Frohna, really came into his own. A key moment was realizing this wasn’t something from the past, but something Adam was actively experiencing. We wanted the audience to feel that same immediacy, so we focused on creating visuals that felt present and real, avoiding anything that felt like a traditional flashback.

You know, as a total movie buff, it was honestly wild seeing my life – or, a version of it – up on the screen. But experiencing it with an audience? That was something else entirely. It felt incredibly surreal, like watching a dream unfold, and I kept thinking, ‘Is this really happening?’

It’s a really odd movie, but in a beautiful way, especially those detailed scenes we were discussing. I’ve watched it so many times now – around fifty – and I still notice new things each time. For example, when Aaron starts watching himself in one of the earlier scenes, the way Jay and Jim developed that EMDR sequence felt really authentic – like a moment where you start to understand something and the intensity begins to lessen. But honestly, I love watching it with an audience. Ultimately, though, I’m a comedian, so I’m most interested in what makes people laugh. I know the emotional moments are coming, and I welcome them, but I’m really listening for the laughter.

ScreenRant asked about the actors joining the project, noting the strong cast including Lucy Boynton, David Duchovny, and Kaitlyn Dever. They were curious if the interviewer had collaborated with any of them previously.

I’d only worked with Kaitlyn previously, having made a film called ‘Outside In’ with her. She’s truly exceptional. When it came to the rest of the cast, Fred and I were very selective. Once Cooper joined the project, he suggested Lucy, who I wasn’t familiar with. We were all looking for talented, emotionally open, and funny people who could understand the delicate balance we were aiming for—making audiences both laugh hysterically and cry. It took time to assemble the right group, especially since this was an independent film and nobody was expecting to get rich from it. We built the cast gradually, and I’m incredibly happy with how it turned out. A big challenge was creating a believable family dynamic. I think Cooper and David look like they could be father and son, Lucy resembles Hope’s daughter, and Kaitlyn falls somewhere in between. That kind of authenticity is really important to me. I experienced its power while acting on ‘Transparent,’ where my on-screen sisters resembled me, and I saw how much it resonated with viewers. If you believe in the family, you’re invested in the story, and that’s what really matters.

ScreenRant asked what projects everyone is currently developing. They were curious if there was anything new in the works that could be shared, knowing the team is busy.

I’m really excited about a project I’m working on right now! It’s a buddy movie with my friend Rory Scovel – he’s a hilarious comedian, and we both think it’s going to be something special. We’re eager to share it with everyone when it’s finished.

I’m really looking forward to people seeing my new movie! I’m currently filming ‘Buy Nothing,’ directed by Bob Byington, who’s a filmmaker from Austin. It’s actually the first time I’ve been back to Austin to work on a project since I moved away in 2003.

Cooper Raiff: I’m directing a movie in New Mexico soon, but I can’t say anything about it yet.

Be sure to dive into some of ScreenRant‘s other SXSW coverage with:

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  • The Fox Review
  • I Love Boosters Review
  • Dead Eyes Review
  • One Another Review
  • Kill Me Review
  • Ready or Not 2: Here I Come Review
  • The Saviors Review
  • Family Movie Review
  • Power Ballad Review
  • Seekers of Infinite Love Review
  • Mike & Nick & Nick & Alice Review
  • Over Your Dead Body Review
  • Sender Review
  • Normal Review
  • Brian Review
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2026-03-23 23:51