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.”
