Josh Safdie Cast Shark Tank Judge Kevin O’Leary in Marty Supreme for a Reason — You’re Not Supposed to Like Him

Josh Safdie just premiered his new movie at the New York Film Festival, and he brought a truly wild bit of casting with him: Kevin O'Leary. Yes, Mr. Wonderful from Shark Tank. Safdie says he wanted someone you instinctively bristle at, which is... quite a way to talk about your own star, but also kind of the point here.

• Title: Marty Supreme
• Director: Josh Safdie
• Writers: Ronald Bronstein, Josh Safdie
• Premiere: New York Film Festival
• Release: December 26, 2025
• Genre: Sports comedy drama
• Cast highlights: Timothee Chalamet, Gwyneth Paltrow, Odessa A'zion, Kevin O'Leary, Tyler Okonma
• IMDb: 7.6/10 (as of now)

So why Kevin O'Leary?

Safdie explained the choice pretty bluntly. He wanted someone the audience is pre-loaded not to like, and O'Leary comes with that built-in from years of Shark Tank.

"I needed someone who you did not like, and did not like in a deep, unconscious way."

- via The Hollywood Reporter

He also basically said O'Leary is the guy on Shark Tank who leans into being the resident jerk, and that part of the fun for viewers is watching him be that guy. It is a gamble, though, because this is O'Leary's first actual acting role.

Who O'Leary plays

O'Leary shows up as Milton Rockwell, a swaggering, insanely wealthy ink-pen magnate. Think sleek boardrooms, expensive pens, and that cold corporate energy. He is not just rich; he is a looming threat in the story, a walking billboard for slick greed who complicates life for the film's lead, Marty (Timothee Chalamet). Gwyneth Paltrow plays Kay, who factors into Marty’s orbit as well.

Early reactions out of NYFF say the casting actually works and that O'Leary clicks on screen with Chalamet and Paltrow. If you are scoring this like a startup pitch: risky ask, surprising return.

The Shark Tank of it all

This whole move banks on O'Leary's TV persona. Over the years, he has built a brand around being blunt to the point of icy, often brushing off contestants' feelings and telling people straight up that their dreams are worthless. Some viewers love that he does not sugarcoat. Others, not so much.

There are moments that are tough to defend, like when he once questioned why anyone would buy a cheap cat testing kit if getting a new cat is cheaper. Or those offers so aggressively tilted toward him that the entrepreneur walks away with nothing meaningful. That reputation is exactly what Safdie is plugging into here.

Does the bet pay off?

From the first wave of responses, kind of yes. O'Leary taps the persona people already know and amplifies it for a character who is supposed to make your skin crawl. It is inside-baseball casting, for sure, but it sounds like Safdie knew exactly what he was doing.

Release plan

Marty Supreme opens December 26, 2025. If you want a refresher on O'Leary's TV vibe in the meantime, Shark Tank is streaming on Hulu in the U.S.