After the Great Safdie Brothers Split of 2024, movie fans were keen to see how the filmmakers’ solo ventures would pan out. Josh Safdie’s “Marty Supreme” enjoyed some of the loudest buzz of 2025 (sorry, Benny and “The Smashing Machine”). A big part of that came thanks to business personality Kevin O’Leary having been cast in the movie.
The twist: He didn’t just nab a role; O’Leary co–stars as main antagonist Milton Rockwell, a rich sourpuss who alternatively sponsors and menaces ping-pong pro Marty Mauser (Timothée Chalamet), and his performance is winning rave reviews.
The casting made sense. O’Leary has long played the villain on reality-TV hits “Dragons’ Den” and “Shark Tank,” and is a polarizing figure off-screen as well.
He had a failed run for the Conservative party leadership in Canada in 2017, and he is a vocal supporter of Donald Trump’s pro-business policies. Last month, he appeared with the U.S. president and Nicki Minaj at an event promoting Trump’s children’s investment account plan.
“I am not a shill for any politician at all,” O’Leary told the Star. “What I endorse or don’t endorse, whether it’s Carney or Trump or any politician, is policy, because policy outlasts politicians.”
In 2019, O’Leary and his wife Linda’s boat collided with another on Lake Joseph, killing two of the other boat’s passengers. Charged with careless operation of a vessel, Linda was found not guilty in 2021. A flurry of civil suits and countersuits stemming from the incident were settled recently, while this week O’Leary won $2.8 million in a defamation judgment against a crypto influencer who called him a “murderer” online and posted his private phone number.
With “Marty Supreme” vying for nine Oscars and “Shark Tank” swimming into the back half of Season 17, we caught up with O’Leary via video call.
How did Safdie first approach you?
One of the producers reached out to (my lawyer) and said, “How do we get a hold of Kevin O’Leary?” I get a lot of these requests and usually they’re little funky chickens. Then (my agent) called me up and said, “Before you say yes to this, remember you’re a reality-TV star, you’ve never done scripted, and you’re not an actor. You’re just a guy on TV and we’ve built a nice business with you over 17 years, so some of us think there’s risk that you’ll s—t the bed.”
And I said, “Well, how do you know I’m gonna s—t the bed? How do I know I’m gonna s—t the bed unless I try it?” Because I have this theory watching all these successful entrepreneurs that I invested in: many of them spend a fair amount of their time outside their comfort zone doing things that they’ve never done before, just to exercise the big muscle of your brain, just to try something new. And that was the whole thesis upon which I did it.
Were you mad that he said you might s—t the bed?
It’s motivational to hear someone say, “Yeah, I don’t think you can do it.”
I heard you flew Safdie up to your lake house to discuss it. Did you do any typical Muskoka things with him? Did you offer him a Caesar, or go jet-skiing, or did you just vibe on the dock?
These cottages are big party zones for friends and family for those six weeks of the summer you’re up there, and I have countless people just hanging around. That week there was a guy named Gene McBurney, who just drops in when he feels like it from the Bahamas. I forgot I printed the script. I left it on the bar and I hadn’t even read it yet, and he picked it up and read it one morning on his own. He knew nothing about Safdie or the movie and he said, “Wow, Kevin, whoever wrote this is a very disturbed individual, but I can’t stop turning the pages — and you’ve gotta be Milton Rockwell.”
I said, “Who’s that?” He said, “Read it: you’re gonna see you’re the guy.”
And this is a data point: somebody who knows nothing about it, is riveted by the story — that, I think, is the essence of every project. If you have a s—t story, you have a s—t movie. And so (Safdie and I) just riffed on the script that day. Safdie just said, “This works for us; you’re gonna get an offer,” and then he got back on the plane and went to New York. The next day, boom, I’m in the movie.
What was the hardest part of the prep? How did you memorize your lines?
My neighbour’s Harry Hamlin. So I went over to see Harry and I said, “Look at the size of this freaking telephone book, how am I gonna memorize this?” And he said, “Here’s how it works, big guy. You’re gonna pull all the scenes that you’re in and you’re gonna memorize everybody’s lines, not just your own, scene by scene by scene.”
What was the biggest challenge in switching from TV to film?
The cinematographer would spend an hour lighting what was gonna be four seconds in the movie. It’s just mind-numbing how long it takes, so it just drove me out of my freaking mind.
And one day I said to Josh, “OK, Josh, we just did 10 takes, I think we got it, we can move on,” and the whole set just froze. I looked around and said, “Oops, did I say something wrong?” A film set is not a democracy. You never say that because the director decides when you move on, and he just laid into me.
What was it like working with Gwyneth Paltrow?
I knew her: we met three years earlier on the set of “Shark Tank,” when she was a guest shark. So it was easy. Even though we were adversaries and she was an unfaithful, nasty wife to me, it was easy to play that role with her.
She has a remarkable talent that a lot of people don’t know until you see it in person: she acts without saying anything. Like when she walked into the living room in that 1950s robe, she looked like a classic star from the early Hollywood era: straight, really tall, really beautiful, and she didn’t even say anything. All of a sudden you knew you were in the 1950s, and it was so easy to just imagine she was my wife at the moment, and we’re fighting about something.
You’ve led a very interesting life, but what was going through your mind when you’re standing there, beating this famous actor with a ping-pong paddle during the famous spanking scene?
Well, excuse my French, but I remember exactly what I was thinking. I said to myself, “How the f—k did I get here?” It’s surreal. It’s 3:30 in the morning, by the way. Chalamet decided that he didn’t want the stunt ass; he wanted his own ass. He wanted to immortalize his own ass in this movie.
And Josh at that hour wasn’t getting what he wanted. He said, “You’re faking it, you’re holding back — it doesn’t look real. You’ve got to hit him.” And I said to Timmy, “You really want me to do this? I mean, the stunt guy’s still here.” He said, “I want it. Hit me.”
I whacked his left cheek so hard that it imprinted the brand of that paddle on his ass. We kept rotating cheeks because one would get really red and we’d have to let it calm down and then hit the other cheek. It was take after take after take because it’s a single camera.
I remember when that thing was over, at 7:00 or maybe 6:45, and I went back to Casa Cipriani on the water where I was staying. They start breakfast at 6:30 and I got there right at the beginning. I said to the guy, “Look, I want the scrambled eggs. I want the salmon. And I want you to go downstairs and get me a 2002 Puligny-Montrachet out of the cellar.” He said, “Sir, it’s seven in the morning.” I said, “Not for me, it’s not.” And I called my wife and said, “Look, I got Montrachet going up here with scrambled eggs.” And she said, “What are you, nuts?” I needed something to calm down. My head was exploding and I was just — it was so crazy what we had done. But now that I see it in the movie, it really worked.
What still sits with you about the experience?
You are suspended in this surreal world. I got right into it. I mean, it was really magical. And I think that must be what acting is, because I’ve never taken any acting lessons. I probably never will, but I got the bug now. I’m doing this again for sure.
Are you going to attend the Oscars?
I’m going to every event. I’ve gone to every opening. I figured, I worked so hard on it, why wouldn’t I finish this journey? I’ve had a really interesting time, getting to know Josh and Ronnie (Bronstein), those sick puppies who wrote this story, so we talk a lot, text every day about all the things that are happening.
Also, this is what I’ve learned: there’s a pecking order in Hollywood. The bottom single-cell amoeba is music. One above it is television. Way above that are feature films. And the reason feature films are at the top of the pecking order is I’ve noticed the food is better, the parties are better. Every single fashion brand on Earth is trying to dress me in their clothes. And jewelry brands and watch brands. I’m a kid in the candy store. I just did a fitting in New York at Dolce (& Gabbana). I’m just going crazy with this stuff. It’s just too much fun.
What makes you happiest these days?
I don’t need more money, I need more time. So I want to do things that are extraordinary. I’m very fortunate I get to do whatever I want. I want to be a better guitarist, for example. I was very fortunate to meet John Mayer. He’s a big “Shark Tank” fan. I learned a lot from him. I’m never gonna be as good as he is, but I could try, and so that keeps me busy.
I know millions of people know me, but my core inner circle is no more than 20 people that I care about. People say, “How do you deal with all the hate mail and all the stuff you get being controversial?” I don’t care! I have never found that getting people to like me is a goal.
The only thing I ask for is respect. The people I respect the most are the ones that write me two-page essays about how much they hate me and then put it out on social media. I actually respond to them because they invested their personal time in that diatribe and they actually invested in me that way.
I mean, you gotta respect that.
This interview has been edited for length and clarity.
