From Shark Tank to A24: Why Kevin O’Leary is Hollywood’s New Favorite “Billionaire Villain”

When Hollywood needs a rich a--hole, they know who to call. But it's not every day that a reality TV star lands a major film role using the exact same insult that launched his career 20 years ago. Kevin O'Leary, the man known as 'Mr. Wonderful' on Shark Tank, is making his big-screen debut in A24's upcoming awards contender, Marty Supreme.

The Same Pitch, Two Decades Apart

According to Entertainment Weekly, director Josh Safdie reached out to O'Leary with a specific vision. He needed someone to play Milton Rockwell, the wealthiest man in America in 1952. Safdie's pitch was blunt: "We're looking for a real a--hole—you're it." O'Leary recalled hearing those exact words from producer Mark Burnett back in the early 2000s when casting for Shark Tank. "I'm starting to think this a--hole thing's working for me," O'Leary joked.

Power Moves and Private Jets

O'Leary didn't follow the typical Hollywood path to casting. When asked to fly to New York for a reading, he refused, insisting the production team visit him at his lake house in Canada instead. He even sent his private plane to fetch Safdie and co-writer Ronald Bronstein. Despite warnings from his agent that he might "s--- the bed" due to his lack of acting experience, O'Leary embraced the role, performing alongside Timothée Chalamet. He noted that he didn't need acting lessons because he simply "immersed himself in the moment," much like his 18 years on reality TV.