“I’m starting to think this a—hole thing’s working for me.”

Kevin O’Leary was cast in *Shark Tank *and Marty Supreme for the same reason

"I'm starting to think this a--hole thing's working for me."

By Mike Miller

Mike Miller

Mike Miller is the executive editor on the movies team at . He previously worked as a writer-reporter for PEOPLE and TMZ.

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December 26, 2025 11:00 a.m. ET

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Kevin O'Leary in 'Marty Supreme'. Credit:

- Kevin O'Leary says *Marty Supreme *director Josh Safdie approached him for the role of Milton Rockwell in a remarkably similar fashion to how he was cast on *Shark Tank *nearly 20 years ago.

- O'Leary says he refused to read for the part in New York City as requested, instead insisting Safdie travel to meet him at his lake house in Canada.

- The reality star, who says he already has multiple offers for other acting roles, reveals what it would take to get him back on a movie set.

When Hollywood needs a rich a--hole, they know who to call.

Whether it's reality TV or A24's latest awards hopeful, provocative multimillionaire venture capitalist Kevin O'Leary is happy to be of service.

While recounting how he landed his big screen debut opposite Timothée Chalamet and Gwyneth Paltrow in Josh Safdie's *Marty Supreme*, O'Leary couldn't help but point out the similarities to his casting in the show that made him famous, *Shark Tank.*

"Over a year ago, I got a phone call from Josh, and he said, 'I am casting for a movie called *Marty Supreme*, and there's a role in it called Milton Rockwell," O'Leary tells *.* "He's the richest man in America in 1952, and we're looking for a real a--hole — you're it.'"

Not everyone would take that as a compliment, but for O'Leary, it brought up good memories.

"I heard that before, 20 years earlier at a place called Shutters, very close to where I am now in L.A. It's a hotel on the beach where I met Mark Burnett for the first time," he recalls. "They were casting for the *Shark Tank *format, and they invited me for breakfast...He said, 'Look, I'm casting for *Shark Tank, *and I'm looking for a real a--hole, and you're it." **

Kevin O'Leary and Timothée Chalamet in 'Marty Supreme'.

Courtesy of A24

Laughing at how history repeats itself, he jokes, "I'm starting to think this a--hole thing's working for me."

On *Shark Tank*, a show where would-be entrepreneurs pitch their products to a panel of investors, O'Leary filled a role similar to that of Simon Cowell on *American Idol*, providing brutally honest feedback with a cocky, know-it-all bravado that often led to entertaining clashes with his fellow Sharks, particularly his foil, billionaire Mark Cuban. The show has won five Primetime Emmys and, by its sixth season, was reaching nine million viewers per episode.

One of those loyal viewers is Ronald Bronstein, Safdie's co-writer on *Marty Supreme. *

"Ronnie is a huge *Shark Tank* fan," O'Leary shares. "I think he's seen every episode because he asked me about products from like 10 years ago. I remember all the products. I don't necessarily remember the people, but I certainly remember the products."

See Timothée Chalamet transform into a ping-pong hero in the trailer for Josh Safdie's 'Marty Supreme'

'It always starts with the face': Building the 'Marty Supreme' ensemble cast, from pros to newbies

The story of how he first met Bronstein sounds a lot like one of Rockwell's interactions with Chalamet's titular ping-pong champion in *Marty Supreme.*

When Safdie asked him to come to New York to read for the part, O'Leary was enjoying his summer vacation and didn't feel much like traveling: "I said, 'I get very little time off. I have a lake house up in Canada where I like to hang out on the dock. I'm there now…I don't want to get on a plane to New York. I'll send a plane for you; you come and see me on the dock.'"

So, Safdie, Bronstein, and producer Eli Bush got on O'Leary's plane and flew to him.

Before his guests arrived, O'Leary printed out the *Marty Supreme* script to familiarize himself with the role. But, he says, "Then we had a big dinner party, and I forgot about it, and it was left sitting on the bar."

Mark Cuban, Jamie Siminoff, Kevin O'Leary, Lori Greiner, and Daymond John on 'Shark Tank'. Eric McCandless/ABC

The next morning, he found one of his guests sitting outside reading it. "He looks up, and he says, 'Kevin, have you read this thing? And I said, 'No.' He said, 'This is the craziest f---ing story I have ever read. This is sick. The guys who wrote this are twisted."

That "berserk" reaction "from a completely random guy" is part of what convinced O'Leary to take the role. "I think that is the whole story of the movie, because you can get that kind of a reaction independently without any prompting of any kind, which is what happened there," he says.

But not everyone in O'Leary's circle was convinced he should take the leap to the silver screen.

Recalling a conversation with his agent, O'Leary says he was warned, "You might s--- the bed… You don't know what the f--- you're doing as an actor. You've never done it. You don't know scripted."

In typical Rockwell fashion, O'Leary says he replied, "I don't give a s---. I'm gonna do it."

It was a risky decision, especially for someone who says he never considered dramatic acting. "I'm a very fortunate guy," he admits. "I don't need more money. I need more time. And I want to use my time to do things that are extraordinary. I want to try things I've never done that are well outside of my comfort zone. And this certainly was."

Timothée Chalamet in 'Marty Supreme'.

Once he signed on, he had no regrets. But, he admits, "What I was concerned about going into it, having never done scripted, was: Could I immerse myself in the moment, so that I wasn't acting?"

He adds, "Because I've never taken any acting lessons. I don't know what the rules of acting are. I'm never gonna take acting lessons. But I know what it's like in reality TV when I just lose sight of the cameras and everything, and I'm just in the moment, shooting *Shark Tank*. I've been doing that for almost 18 years now. But I said, 'When is that gonna happen to me on this? At what moment am I no longer conscious of being on a film set?'"

O'Leary credits Safdie for creating an environment where he could easily slip into Rockwell's skin. "I was never in a situation where I didn't feel totally in the moment," he says. "I was always right in it. I was not acting."

Plus, performing alongside an actor like Chalamet also helped. "His method, at least in front of me, was to get up and go find his character," he says of the *Dune *star. "He would just do a circle around a light stand or something and just come back in character. I'm not kidding, like *in character*. Boom, sparks are flying off his fingertips."

Timothée Chalamet and Kevin O'Leary in 'Marty Supreme'.

He jokes, "It's real easy to be Milton when I've got that little a--hole in front of me doing his thing."

Now that he's had this experience and is earning rave reviews for his performance, might he answer the call if there's another famous director in need of a rich a--hole?

"I've been offered two scripts," he reveals. "I haven't read 'em yet."

But, he adds, "I'd like to ride this one out for a while first and see where it goes and all the rest. Scheduling's a bitch for this filmmaking stuff."

If he does find the time, he says he'll look for a script that gives him the same type of reaction his friend had on the dock. "It's the story at the end of the day," he says. "If the story isn't good, how could the movie be good?"

Spoken like a true actor.

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