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How Kevin O’Leary Made His ‘Marty Supreme’ Character More Cutthroat

January 4, 2026
in News
How Kevin O’Leary Made His ‘Marty Supreme’ Character More Cutthroat

The director Josh Safdie’s first call to the “Shark Tank” judge Kevin O’Leary was blunt.

After Safdie explained the part he was trying to cast in his new table tennis drama, “Marty Supreme,” O’Leary, 71, said the filmmaker told him, “We’re looking for a real [expletive], and you’re it.”

It wasn’t a small role, either: O’Leary, a.k.a. Mr. Wonderful, the Canadian investor known for his candid, no-nonsense reality TV persona, would play Milton Rockwell, a wealthy businessman holding the purse strings for Timothée Chalamet’s Marty Mauser, a confident hustler with big dreams.

“I read the script, and I was like, ‘This is extraordinary,’” O’Leary said in a recent interview.

O’Leary, who is making his film debut in the role, was among a cast of around 150, including several musicians, comedians and other nonactors like the rapper Tyler, the Creator; the basketball star Tracy McGrady; and the fashion designer Isaac Mizrahi.

They were assembled by the casting director Jennifer Venditti, a longtime collaborator of both Josh and his filmmaker brother, Benny. “What Josh and I are always looking for — whether it’s an actor or someone who’s never acted before — is someone whose real life informs their character,” Venditti said in a recent video interview. “Kevin was a perfect example.”

In an interview, O’Leary discussed the reasons he decided to try film acting, the changes he suggested to make his character more ruthless and a deleted scene he wishes had made the final cut. These are edited excerpts from the conversation.

What was your first meeting with Josh Safdie like?

Eli Bush, a producer on the film, said, “We’d like you to come down to New York.” And normally, I would have said yes, but I was hanging out on my dock [in Ontario]. My family and friends were up from all around the world. So I said, “How about this? I’ll send a plane down for you. You guys fly up here.” I was surprised when they said, “Let’s do it.” They got up really early, and by 7:30 in the morning, we were watching the sun rise on my dock and reading the script.

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What was your first impression of the material?

They sent me the PDF three or four days before, and I printed two copies because I wanted to make notes. A longtime friend of mine, the banker Gene McBurney, decided to drop in. He got up at 5 a.m. to watch the sunrise, and the two copies of the script were sitting on the bar. He took one and started reading it out on the deck. A little later I got up, and I said, “Gene, what are you doing?” He said, “Kevin, have you read this script? This thing is insane. This guy, Milton Rockwell, it’s got to be you. This is crazy — crazy! — whoever wrote this is a very sick person.”

Why that mattered to me is that this random guy reads the story and goes nuts. I thought, “OK, there is an index for you about where this thing could go.” Then others in my family read it and had the same reaction, and by the time the guys showed up, I had the same feeling.

How are you like and not like the character?

I don’t consider myself acting in that role as much as just reading the room, being myself and being what I knew I would be if I were in 1952. I mean, I am Milton Rockwell today, and I would have been Milton Rockwell back then. I didn’t find it hard. I also would give credit to Safdie and [the co-writer Ronald] Bronstein on this, but I was reading it, scene by scene, and saying, “If it was ’52, I wouldn’t say that. I’d say this,” or “I don’t think this is right here.” They would listen and make modifications.

Even my wife made a change. In the bedroom scene where Gwyneth [Paltrow, who plays O’Leary’s character’s wife] is on the phone with Marty, and I walk out and ask if she’d used my razor, that was originally a Q-Tip. But she said, “You guys are idiots. It would never be a Q-Tip. She would have used the razor and made it dull. He would have cut his face. That’s what women do” Ronnie said, “Yeah, that makes sense.”

What are some other changes you suggested?

I had lots of fights with Ronnie — well, not fights, but I said, “Guys, this Marty Supreme guy, I would never let anybody [expletive] me over like this. This would never happen to me, ever. And he is not paying an adequate price.” This is when we’re reading it on the dock. “I’m a vampire. I would bite his neck to put him in hell in perpetuity for what he’s done to me here.” And Ronnie said, “That’s sick. Let’s think about that.” I’m glad that kind of got in there.

I’ve read that you provided the watches your character wears. Tell me about them.

I’m a known watch collector. I don’t wear other people’s watches, and I don’t wear props. I’ve got to have a real piece. I would never, ever wear a fake watch or some prop — I would go to hell if I did that within the watch-collecting community. So when I understood what was required after our dock meeting, I went to work. I called up Rolex, and I said, “Guys, I’m going to need on my left wrist, New York time. I want a Patek Philippe from the ’50s. It’s got to be functioning. And I want to buy it. Go find it.” We scoured the friggin’ Earth for that watch.

Then for the brands out of Japan, there was no Grand Seiko or Credor in 1952, but there was Seiko, and they had a watch called the Super. It was for collectors at the time, and we could not find one in the secondary market. But then Seiko found one — it might have come from some museum — and they gifted it to me.

So in the movie, on my left hand, I’ve got New York time, and on my right I have Tokyo time, which Milton would have done, because he’s doing business in both locations. I’m wearing them now as I’m speaking to you.

There’s a scene that didn’t make the cut — I want to see it one day — where I’m saying to Marty, “If you listen to what I’m telling you, and you do what I say, one day, you too will be able to wear two watches, with two time zones. You will be so successful.” I love that scene. Obviously, Josh didn’t.

Do you want to do more scripted roles?

Yeah, I’m really intrigued because my agent, Jay Sures, had initially said to me, “Look, Kevin, I have to be transparent. You are not an actor. You’ve never done scripted. You could [expletive] the bed.” And I said, “Jay, how do you know unless I try this?” I like to try things outside my comfort zone. I’m very fortunate in life. I don’t need more money; I need more time, and I want to use my time to do things that are extraordinary. I’d read the script, and I was charged up, so I said, “I’m gonna do it.”

Sarah Bahr writes about culture and style for The Times.

The post How Kevin O’Leary Made His ‘Marty Supreme’ Character More Cutthroat appeared first on New York Times.

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