Jay Duplass on Returning to Directing, AI’s Ethical Dilemmas and His Sundance Film ‘See You When I See You’

Jay Duplass is back where he always wanted to be — behind the camera.

In the early aughts, Jay and and his brother Mark exploded on the indie scene with low-budget mumblecore offerings like “Cyrus,” “Baghead” and “The Puffy Chair” that were produced for a fraction of the price of most features. The siblings were scrappy self-starters with an entrepreneurial streak, and, for awhile, they embodied a kind of DIY filmmaking that paved the way for other directors to operate outside the studio system. In recent years, however, the brothers found themselves in greater demand as actors. Mark Duplass appeared in everything from “Zero Dark Thirty” to “The Morning Show,” while Jay Duplass scored raves for his supporting turn in “Transparent.”

But deep down, Jay Duplass still wanted to be calling the shots. In 2025, he directed “The Baltimorons,” a comedy about a man in desperate need of emergency dental surgery that won the Audience Award at SXSW before getting picked up by IFC and Sapan Studios. It was the first movie he directed in 13 years and one of the only ones he made without Mark.

“It felt like a comeback,” Duplass says during a recent sit-down at Variety‘s midtown Manhattan office. “And it felt good to be doing what I really love again.”

Duplass has followed that up with “See You When I See You,” an adaptation of Adam Cayton-Holland’s memoir “Tragedy Plus Time: A Tragi-Comic Memoir.” The film dramatizes a comedy writer dealing with his sister’s suicide and stars Cooper Raiff, one of the Duplass’ directing protegés, as well as David Duchovny, Hope Davis and Kaitlyn Dever. “See You When I See You’s” mixture of humor and tragedy resonated at the Sundance Film Festival, where the film earned a standing ovation at its world premiere.

“I cried really hard when I read the script and I laughed really hard too,” Duplass says. “This is a family that is very intelligent and very good at navigating life in general. But this is so much bigger than them and it really sends them spinning. And I think a lot of people can relate to that feeling.”

Over a wide-ranging conversation, Duplass talked about orchestrating “See You When I See You’s” tonal shifts, as well as the struggles of making personal films in an industry that loves to sand off all the edges.

Until “The Baltimorons” was released last year, you took a long break from directing features. What was behind that gap?

The last movie Mark and I made together was in 2012 with “Jeff, Who Lives at Home.” Mark started to become kind of a famous actor around that time. Then the mini-major studios where we worked were going away as TV and streaming were becoming bigger. So we did “Togetherness” for HBO as a TV show, and then I became an actor accidentally when I was hired for “Transparent.” So that set me down this path of acting in other people’s movies and shows. At a certain point I realized, I miss making movies. That’s actually where my heart is. It’s always been there.

What appealed to you about “See You When I See You”?

It is a little bit of an heir to “The Big Sick,” but the humor is darker and it’s more tragic, because someone has died in this story. This movie is about when terrible things happen, are you going to be able to climb out of it? Some people talk about it as a grief movie, because this family is grieving the loss of the daughter. But that’s not really what the plot is about. The plot is about this kid who has PTSD, and he doesn’t know it.

What made you think of Cooper Raiff for the lead ?

A long time ago, Cooper tweeted at me, “You’re my favorite filmmaker! I dare you to watch this thing I made.” And I watched this little documentary and eventually I helped him develop that into his first movie, “Shithouse.” So I was kind of like ghost producer movie dad for him and we’ve been close ever since. Now, “See You When I See You” is not a cheap movie, so most companies would probably want somebody famous in that role. And even though Cooper is known, he’s not selling territories overseas. But, he has this very unusual combination of having emotional access to everything, and being very funny and willing to laugh at himself. I just couldn’t find anyone else with that level of confidence and as well that level of vulnerability. It had to be Cooper.

You used to direct as a duo with your brother Mark. Do you still work together?

Mark and I are still super close. Even though we’re not directing together, we’re running a production company. We’ve been able to consciously uncouple as writer-directors. We’re actually getting along better now than ever. There’s something about being a director team, that puts you on this forced march. You’re spending so much time together. It was weird to go to a party and have somebody be like, “where’s your brother?” It’s like, “I am a full fledged human being.” I don’t need someone to finish my sentences, even though that’s what we will do if we are together. Now, we’re still sharing ideas, but when we get together, it’s because we decide to get together.

Does one of you like directing more than the other?

Honestly, it took us like 13 or 14 years to figure out that I can’t live without directing and that he is not that interested in it at all. He’s definitely much more of a producer. He likes to have a lot of things going on and to apply a light touch to all of them. I just want to do one thing. I want to pour all my concentration into that project.

Has your experience acting changed the way you direct?

It’s taken the preciousness out of it. It’s made me more comfortable with actors and acting.

When you started out, you got a lot of attention for making micro-budgeted movies. Your first film, “The Puffy Chair,” cost $15,000. Digital technology has made it possible to make movies cheaply and platforms like YouTube have made it easier to distribute work. But is it harder to get attention for the movies people make today?

It is harder to get movies seen overall, just because there are so many more movies being made. It’s so competitive. That said, it’s incredibly difficult to make a good movie. Everything has to come together. It’s wonderful that we have democratized the process and that people feel more empowered. I just don’t know if people have enough fear and respect for how hard it is to really pull it off. It’s a very complex art form. Buyers have told me there are a lot of movies out there, but there aren’t a lot of good movies.

What are your thoughts about AI? Obviously, it’s very disruptive and it could lead to fewer jobs, but it also has the potential to lower costs, which could result in more artistic freedom.

It’s scary, and it’s scary exciting. There’s a movie that I would like to make that cost $12 million and it’s been hard to set it up. And someone recently proposed to me that that movie could easily cost $6 million if I used AI for the complex, big, sweeping scenes I want to shoot. And I was like, “Well, I don’t want to take the jobs away from people that would get that job.” And they were like, “Well look at it this way. If you can’t get the movie made, nobody is going to get any jobs.” I don’t know how I feel. Ethically, it’s something that I’m still mulling over.

What about AI generated movies? Do those scare you?

Not really. AI is taking all these elements that audiences have liked before and putting them all together. It’s like audiences like dogs and flying people and cities exploding. We’ll throw them in one script. But when you combine all those things it just feels cookie cutter.

I keep reading obituaries for cinemas. Do you feel optimistic about the state of indie film?

I do. I think audiences are starting to come back. It’s still tough out there. We’re competing with TikTok and streaming. That’s what we’re all up against. But I have faith. This is the art form I grew up on. You know what my least favorite word in our industry is? “Content.” I’m not making content. I’m making a fucking movie. I’m making a piece of art.