Kevin O’Leary has been called a lot of things in his life — “Mr. Wonderful,” TV personality, entrepreneur — but “real asshole” might be the most unexpectedly useful.
It’s the description director Josh Safdie gave him when offering the role of Milton Rockwell in Marty Supreme. And it’s not even the first time O’Leary has been cast that way. When Shark Tank launched 20 years ago, producers told him they were looking for a real asshole and thought he’d be perfect.
“So this theme has been working for me for a long time,” the 71-year-old Canadian businessman laughs to Yahoo. “It’s sort of full circle.”
Full circle, but with a twist.
O’Leary never expected to find himself starring opposite Gwyneth Paltrow and Timothée Chalamet in one of the buzziest films of the year, let alone emerge as one of its most-talked-about performances. Yet somehow, improbably, he fits. As a billionaire socialite with a razor-sharp tongue, O’Leary doesn’t just make a cameo — he hijacks the screen.
How did Kevin O’Leary end up in this movie?
The path from Shark Tank to the Safdie-verse didn’t involve an audition or a Hollywood lunch. Instead, it started at O’Leary’s lake house.
Safdie and cowriter Ronald Bronstein had written the role of Rockwell and were still searching for the right person when O’Leary entered the picture. According to O’Leary, the part had been difficult to cast — so he made them an offer: Come to him. He wasn’t flying to New York. If they wanted him, they could sit on his dock and read the script together.
Before they arrived, O’Leary printed the script — “the size of telephone books” — and left it on the bar. A longtime friend staying at the house woke up early, started reading and couldn’t stop. Marty Supreme tracks a charismatic hustler (Chalamet) navigating money, power and ambition — with competitive Ping-Pong at the unlikely center of it all. O’Leary plays Paltrow’s onscreen husband.
“He said, ‘Kevin, have you read this thing? This is insane. You’ve got to be Milton. This Milton guy is a bad guy, and he’s you,’” O’Leary recalls.
That endorsement sealed it. When Safdie, Bronstein and producer Eli Bush arrived, they didn’t just read the script — they began shaping the character around O’Leary himself.
“I started to say to them, ‘Look, if I was Milton Rockwell, 52, a billionaire, richest man in America, I wouldn’t say that. I would say this,‘” O’Leary says. His own net worth is estimated to be around $400 million, according to Forbes.
“They were quite flexible in crafting the story to the way I saw it to kind of melt into the character,” he continues. “And it made it very easy for me to just slide into that role because, you know, I know how to be a billionaire in 1952. That’s not too far from what I do every day. … This is [who] I am.”
O’Leary, center, as Milton Rockwell in a scene from ‘Marty Supreme.” (A24/Everett Collection)
Relinquishing control
O’Leary is not accustomed to being anything but the most powerful person in the room. For decades, whether in the boardroom or on the Shark Tank set, he’s been the one calling the shots — the investor with the final word, the dealmaker whose approval everyone else is chasing. Even in television, he’s built a persona around authority and control.
Marty Supreme required something entirely different. For the first time in his career, O’Leary wasn’t at the top of the call sheet. He wasn’t the boss. He was part of an ensemble … and working for someone else.
“Yeah, that took a while,” he admits of no longer being the one in charge. “I’ve never worked for anybody. So that’s very difficult.”
The adjustment wasn’t just about ego; it was about trusting a process that was fundamentally not his own. At first, O’Leary bristled at the number of takes, the constant recalibrating, the refusal to move on from a scene until every detail was locked.
“But then I realized — hey, I’m with the best guys in the world here,” he says of Safdie. “Why don’t I just chillax and let them tell me what to do?”
Once he let go, the results spoke for themselves.
“I’m pretty happy with the way that worked out,” he says.
That willingness to surrender control extended beyond the set — even into territory where O’Leary is famously meticulous: money.
O’Leary with costars Gwyneth Paltrow and Timothée Chalamet. (John Nacion/Variety via Getty Images)
While Shark Tank viewers know him as a relentless negotiator, he didn’t handle his own deal for Marty Supreme. Instead, he trusted his longtime agent at UTA, Jay Sures, with whom he’s worked for years without a formal contract. (“I just have a handshake,” he says.)
Sures didn’t sugarcoat the risk.
“He did say to me, ‘Kevin, you’ve never done scripted. You could shit the bed on this,’” O’Leary recalls. “And I said, ‘How do I know I’m going to shit the bed unless I try?’ He said, ‘You could really f*** it up.’”
O’Leary’s response was blunt: “I said, ‘I don’t give a shit. I’m going to do it anyway.’”
Even now, he couldn’t tell you what his paycheck was.
“What I got paid, I have no idea,” he says. “I mean, I’ll be honest with you. I don’t know. Whatever I got, they negotiated it. I’m sure I’ll find out one day, but I don’t really give a shit.”
If relinquishing control was the leap, Safdie’s filmmaking style was the safety net. O’Leary speaks about the director with a mix of awe and amusement — particularly his obsession with precision.
“He’s a perfectionist,” O’Leary says. “If one light isn’t perfect, he can’t start.”
The process could be maddening in the moment. Takes stretched on. Scenes were rebuilt repeatedly, sometimes for 40 takes. At times, Safdie and Bronstein would argue so intensely they’d “go yell at each other in the street.”
“It was fantastic,” O’Leary laughs.
Kevin O’Leary in ‘Marty Supreme.’
No acting required
Marty Supreme hasn’t turned O’Leary into an actor. If anything, it convinced him he never was one.
“I actually don’t think I was acting,” he says. “I don’t know what acting is. I don’t know what the rules of acting are.”
He didn’t take acting lessons for the role and says he has no plans to start now. Instead, O’Leary relied on preparation and instinct. He read the script repeatedly to understand the story inside and out, but says, “I never memorized the lines.”
“I’m dyslexic. I’m really shitty at memorizing anything,” O’Leary says. He believes the learning disability is a “superpower” that has helped him succeed in business, and now, on set.
“I knew where we were in the story,” he says. “I knew what was happening in the room. I could read the room.”
As for what comes next, O’Leary isn’t rushing to define it. He says he’s already been sent two other scripts — though he hasn’t read them yet — and for now, he’s more focused on enjoying what he just accomplished.
“How do I get better than this?” he asks. “To me, this is the pinnacle of filmmaking.”
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