Kevin O’Leary: A New Chapter Beyond the Tank
Kevin O’Leary, the famously blunt and shrewd investor known for his roles on Dragons’ Den and Shark Tank, has surprised audiences with a captivating performance in Josh Safdie’s critically acclaimed film, Marty Supreme. The business mogul isn’t just dipping his toes into acting; he’s fully immersed, earning rave reviews for his portrayal of Milton Rockwell, a wealthy and often antagonistic figure in the film.
The Unexpected Role
Following the creative split between the Safdie brothers in 2024, all eyes were on their individual projects. Josh Safdie’s Marty Supreme quickly became a frontrunner for awards buzz, largely thanks to O’Leary’s unexpected casting. He embodies Milton Rockwell, a character who both sponsors and torments ping-pong prodigy Marty Mauser (Timothée Chalamet). The role feels surprisingly natural for O’Leary, given his established on-screen persona.
“I get a lot of these requests and usually they’re little funky chickens,” O’Leary shared in a recent interview. “But this one felt different.”
Why Acting? Embracing the Challenge
Despite his success in the business world, O’Leary was drawn to the challenge of acting. He explained his philosophy: “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.” He saw acting as an opportunity to push his boundaries and explore a new creative outlet.
His agent initially expressed reservations, fearing the risk to his established brand. However, O’Leary was undeterred. “How do I know I’m gonna s—t the bed unless I try it?” he countered.
Behind the Scenes with Safdie
O’Leary recounted a pivotal moment when he discussed the script with Safdie at his lake house. A guest, Gene McBurney, picked up the script and, without knowing anything about the film, declared, “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.” This unsolicited feedback solidified O’Leary’s decision.
The Demands of Filmmaking
Transitioning from reality television to film presented unique challenges. O’Leary was struck by the meticulous nature of filmmaking. “The cinematographer would spend an hour lighting what was gonna be four seconds in the movie,” he noted. He also learned quickly that a film set operates differently than a television studio. “A film set is not a democracy. You never say that because the director decides when you move on.”
The Infamous Spanking Scene
Perhaps the most talked-about scene in Marty Supreme involves O’Leary’s character physically disciplining Chalamet’s. O’Leary revealed that Chalamet insisted on performing the scene himself, without a stunt double. “He wanted to immortalize his own ass in this movie,” O’Leary chuckled. The scene required multiple takes, and O’Leary admitted to needing a celebratory glass of Puligny-Montrachet and scrambled eggs afterward to decompress.
Beyond the Film: A Newfound Passion
With Marty Supreme garnering nine Oscar nominations and Shark Tank continuing its run, O’Leary is embracing this new chapter. He’s enjoying the perks of Hollywood, from designer clothes to exclusive parties. But beyond the glamour, he’s discovered a genuine passion for acting. “I’m doing this again for sure,” he affirmed. He’s also continuing to pursue personal interests, like improving his guitar skills with guidance from John Mayer.
A Lasting Impression
Kevin O’Leary’s foray into acting has proven to be a resounding success. He’s not seeking validation or approval, but rather respect for his willingness to take risks and explore new horizons. As he puts it, “The only thing I ask for is respect.”
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