Kevin O’Leary is trying something completely different. The sharp-edged face of Shark Tank is making his first major move into acting with Marty Supreme, a ping-pong-centered drama film directed by Josh Safdie starring Timothée Chalamet as the titular lead. Kevin plays the character of Milton Rockwell in the movie.
Kevin O’Leary’s Hollywood Acting Debut
In the movie, O’Leary plays a rich businessman who is very dislikeable. The role evidently leans into his tough public image without directly copying it. It is a surprising shift from the boardroom to the big screen for Mr. Wonderful, who appears alongside ex Shark Tank celebrity investor Gwyneth Paltrow.
Several familiar Shark Tank faces showed up at the premiere. Barbara Corcoran, Robert Herjavec, Daniel Lubetzky, and former Shark Tank investor Mark Cuban posed for photos with Chalamet and Safdie, among others.
The scene carried over into the after-party, where Hollywood regulars mixed with New York personalities. Guests included Mayor Zohran Mamdani, Anna Wintour, Tyler Gregory Okonma, Jack Harlow, Julia Fox, Chloë Sevigny, and The Dare. Barbara Corcoran even posted a story for Kevin O’Leary and captioned it “A star is born!”
Acting Leaves Kevin O’Leary Wanting More
O’Leary also took to Instagram to thank his Shark Tank crew. He thanked his Shark Tank mates for showing support for his acting debut. He also leaned into the humor, teasing whether this new chapter might lead to some unexpected celebrity pitches down the line.
O’Leary said in an interview with The Hollywood Reporter that the role came naturally because he did not try to become someone else. He just leaned on his natural instinct. The idea of acting rules or formal training does not interest him, and he says it never has. He even joked that if he had been alive in the early 1950s, that character would have looked a lot like him.
The Shark Tank investor was quick to say in the same interview that his blunt Shark Tank image is not something he puts on for the camera. That is just how he is. When told that Safdie cast him because he wanted someone audiences instinctively dislike, he took it as a compliment.
Kevin responded by saying, “I love it. I cannot please everybody. I just tell the truth.”
It is safe to say that Mr. Wonderful quite enjoyed his acting experience. After his first big-screen role, he said acting has him hooked. It even changed his views and perception of the arts and creative pursuits.
Kevin O’Leary on Creativity, AI, and the Filming Process
Filming the movie also shifted how Kevin thinks about AI and creative work. Being surrounded by top-tier craftspeople had a lot to do with it. Working alongside veterans like production designer Jack Fisk and cinematographer Darius Khondji gave him a front-row seat to how much care goes into every detail.
The slower pace caught him off guard. “We didn’t shoot until Darius was happy with everything, and I thought, what a pain,” he said. Kevin was comparing the ordeal to his reality TV experience. He said, “I’m used to reality TV. We bang out multiple episodes in one day.”
He further added, “What specifically changed my view was the fact that so much of the improvised lines made it into the final cut. That only happens in the magic of 4 a.m., when somebody says something that the other actor riffs off of.”
The Meaning Behind Marty Supreme According to Josh Safdie
Director Josh Safdie explained his project, saying, “This movie is about belief — belief in others, belief in self, more than anything. It’s about dreams. It’s a heist film in some ways.”
He went on to add that “It’s about how a dream can, you know, take a heist on faith. It’s about trying to control your fate, and A24 really, really, really, from the very beginning, were one of the believers. … They were one of the squad cars that helped, you know, try to heist the ‘bank of faith.’”
Safdie took a moment to talk about what it meant to premiere the film in New York, a city where parts of Marty Supreme were shot and where many of his earlier projects came together in a much scrappier way.
The director also spoke at length about the crew, calling out individuals and sharing small notes about how they helped bring the film together.
He then brought co-writer Ronald Bronstein onstage, followed by the cast. Gwyneth Paltrow, Odessa A’zion, and Kevin O’Leary each stepped forward as Safdie introduced them to the audience.
A Different Stage for Kevin O’Leary
For someone known for staying firmly in control, this was a rare detour. Kevin O’Leary leaned into a role far removed from his usual world and came out enjoying the process. The experience seems to have opened a new door. Whether he walks through it again or not, this first step already made an impression.
