When audiences flock to theaters on December 25, 2025, to see the much-anticipated film Marty Supreme, they may be surprised to learn that one of its stars, Kevin O’Leary, almost turned down the role. The reality television personality, best known as a judge on Shark Tank, found himself in an unexpected position, contemplating a career shift into acting.
O’Leary revealed that he received the script nearly a year before production began but accidentally overlooked it. “I first got the script about a year ago, then I forgot about it,” he shared. It seems fate intervened when a guest at his lake house stumbled upon the script and was drawn in. “By the time I got up at 9:30, he was still flipping the last pages,” O’Leary recalled. The guest’s enthusiasm prompted O’Leary to reconsider his initial hesitation.
Once convinced of the script’s potential, O’Leary met with director Josh Safdie, known for his work on Uncut Gems. Safdie made it clear that the role of Milton Rockwell, a wealthy businessman in 1952, required a character with a certain edge. “The first thing Josh said was, ‘Look, we need a real a**hole for it and you’re it,'” O’Leary recounted.
Despite the appeal of the role, O’Leary faced skepticism from his talent agent, who cautioned against the risks involved. “They said, ‘Kevin, we built a pretty big franchise for you. We’re not all 100 percent behind this idea of you taking a scripted role,'” he explained. Nevertheless, O’Leary pushed back, emphasizing his desire to explore opportunities outside his comfort zone.
As filming commenced, O’Leary found himself sharing scenes with Timothée Chalamet, a noted method actor. The preparation for their first scene was an eye-opener for O’Leary. “We talked for a couple of minutes before we started about the cadence of what we were about to do,” he said. Chalamet’s ability to immerse himself into character made it easier for O’Leary to embrace his role. “Once he’s the kid, and I’m Milton, it became simple to play off him.”
Despite his lack of formal training in acting, O’Leary approached the role with confidence. “I don’t know what the rules of acting are. I don’t care. I’ve never taken acting lessons,” he stated, leaving the judgment of his performance to the critics.
As Marty Supreme prepares to debut, O’Leary’s unconventional choice to step into a scripted role may not only surprise audiences but also mark a significant moment in his career. The film promises a unique blend of humor and drama, showcasing a dynamic story that challenges the norms of both the film industry and O’Leary’s established persona.
With his performance drawing both intrigue and skepticism, O’Leary is ready to face the consequences of his bold decision. Whether his venture into acting will pay off remains to be seen, but one thing is certain: audiences will witness a different side of the entrepreneur when Marty Supreme hits theaters this Christmas.
