Kevin O’Leary Was Proud to Play a “Real Asshole” in ‘Marty Supreme’
Written by admin on December 21, 2025
“We’re looking for a real asshole, and you’re it.” That’s how director Josh Safdie tried to convince Kevin O’Leary of Shark Tank fame to play an intense ink-pen tycoon in Safdie’s 1950s-set sports dramedy Marty Supreme. O’Leary, the entrepreneur and investor known as “Mr. Wonderful,” was unfazed. He had heard the same thing 17 years earlier, when Mark Burnett’s production company recruited him for the American version of a Japanese reality TV show.
“I say this asshole thing’s starting to work for me,” O’Leary jokes about making his acting debut opposite Timothée Chalamet and Gwyneth Paltrow. “I am not an asshole. I just tell the truth, and some people don’t like it. I think maybe I’m going to become the honorary chairman of all assholes everywhere after this. And it’s a job I’m happy to take.”
Marty Supreme is filled with dynamic visuals, 1980s synth-pop needle drops, and other arresting non-actors, including Isaac Mizrahi, Abel Ferrara, and John Catsimatidis. But O’Leary steals most of his scenes as Milton Rockwell, a no-nonsense New York multimillionaire in a loveless marriage to trophy wife Kay Stone (Paltrow), a former Hollywood star. Chalamet’s pushy Lower East Side ping-pong prodigy Marty Mauser—who is still living with his Jewish hypochondriac mother (Fran Drescher), schtupping his married ex-girlfriend (Odessa A’Zion), and grifting with his pal (Tyler Okonma, a.k.a. Tyler, The Creator)—sees the patrician couple as a means to realizing his dream of becoming the world tennis-table champion.
Milton is taken with Marty’s talent, but he’s no easy mark. Marty’s a hustler with chutzpah; when talking about an opponent who’s a Holocaust survivor, he boasts to a journalist, “I’m gonna do to Kletzski what Auschwitz couldn’t.” Yet Milton tells Marty that he can “smell bullshit from a mile away.” The CEO wants Marty to throw a series of company-sponsored exhibition matches against his deft rival, Koto Endo (Koto Kawaguchi, the real-life winner of the Japanese National Deaf Table Tennis Championships), in Japan. But the ambitious competitor just can’t agree to the deal.
“What I love about this film is it’s a chronicle of the birth of the American dream right after the optimism of the Second World War,” O’Leary tells me. “Yes, it’s got a crazy, kinetic roller-coaster [energy]. But Marty’s like every Shark Tank hustler.”
It helped that Safdie and co-writer Ronald Bronstein tailored the role to O’Leary’s strengths. After O’Leary’s initial Zoom meeting with Safdie, the pair asked him to come to Manhattan. Instead, the 71-year-old venture capitalist flew them to his lake house north of Toronto—and gave them script notes. Unlike Paltrow, who was unfamiliar with the Safdie oeuvre, O’Leary had seen and loved Uncut Gems (cowritten by Bronstein and codirected by Safdie with his brother Benny Safdie) and thought the creatives were “sick puppies, but in a good way.” Working with them only increased his (rare) praise. “They were willing to make changes, which I had a lot of respect for because I know who Milton is. I am Milton.”
So it was easy for the bombastic businessman—who sports glasses and a bit more hair in the movie—to get under Milton’s skin. “I’m just being myself,” he says. There was no need for him to hire an acting coach, or to create a backstory for the character. He didn’t even solicit acting advice from pros Chalamet or Paltrow. (Safdie has said that on Paltrow’s first day of shooting, he was “shocked” to hear her quietly say, “I hope I remember how to do this.”)
O’Leary did, however, take note of Chalamet’s process. During their first meeting in Safdie’s office, “we read two or three lines together. [He’s] pretty amazing….He gets out of the chair, walks away for a second, and he gets into character, and [then] he comes back with sparks flying off him. He’s not Timothée Chalamet anymore. So I saw that happen, and I was totally comfortable with it, and that made it much easier for me to be Milton Rockwell.”
Still, there was one audacious scene, shot at four in the morning that gave O’Leary pause—at least initially. At a black-tie party in the Rockwells’ Fifth Avenue duplex, a contrite Marty begs Milton’s forgiveness for passing on the exhibition matches. Milton tells him that “there are no second chances in life.” When Marty begs, Milton orders the young athlete to drop his pants and bend over. Then he whacks Marty’s bare ass—more than once—with a ping-pong paddle. O’Leary broke the first fake paddle on a stand-in. When it was replaced with a real paddle, Chalamet insisted on doing the scene himself. “I said, ‘Timmy, you don’t want me to hit you—‘cause Josh really wanted it to be intense.” But Chalamet was resolute. O’Leary belted him so many times that “his ass went red, and had the imprint of the paddle on it….I mean, you gotta hand it to the kid. He’s authentic.”
Also authentic were the pricey period timepieces that the script called for Milton to wear. O’Leary, a well-known watch collector, didn’t want replicas—so he had Patek Philippe and Seiko respectively track down a vintage red-band 1952 model and a 1950s-era Super. Seiko actually gave O’Leary its rare watch, with a Japanese flag on the back case. (O’Leary also sports the brand’s watches on Shark Tank.) “I’m gonna bring them in my coffin with me,” he says.
Before that happens, he wants to clarify a few things. A vocal Donald Trump supporter in the run-up to the 2024 election, O’Leary has changed his tune a bit: “I don’t shill for politicians, even Trump. I shill for their policy. So there are Trump policies I agree with, and there are Trump policies I don’t agree with. I did not agree with Trump on banning foreign students. I don’t like the $2,000 free money [for health insurance].” The Montreal-born entrepreneur also doesn’t endorse making Canada the 51st state. Still, he thinks the economies of Canada and the US should be merged, without tariffs, to make both nations more competitive with China. “I took the premier of Alberta down to meet Trump at Mar-a-Lago before the inauguration, [and] they got to know each other,” he says. “And it was a good thing, because there’s no tariff on that oil anymore.”
A couple of months ago, O’Leary also made headlines for saying Marty Supreme could have saved millions of dollars if “AI agents” were used in the film. He’s seemingly had a change of heart: O’Leary now says that AI is merely good for generating background players in scenes that don’t call for them to interact with any human performers.
Having established himself as a principal player—he’s already getting new scripts—O’Leary has been spoiled by his Marty Supreme experience. He wants to work with Safdie and Bronstein again. But he’ll never alter his personality for the sake of a film. “I just try to be authentic. My mother told me years ago [to] always tell the truth,” he says. ”Some people won’t be happy; some will. So that’s what I do. And that’s really what Milton does. Yeah, he’s a dick, but so what? He’s successful because he understands what is signal and what is noise.”
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