Kevin O’Leary, aka “Mr. Wonderful” from Shark Tank, is stepping off the boardroom and into Hollywood — and yes, he’s starring alongside Timothée Chalamet in the highly anticipated film Marty Supreme.
On a recent appearance on TMZ Live, O’Leary explained just how he went from pitching sharks to sharing the big screen with one of Hollywood’s hottest stars. And the answer? He may have been typecast as the ultimate ahole** — and he’s leaning into it.
“The director and the writer came to me looking for a real a**hole to play Milton Rockwell, one of the wealthiest men in America in 1952,” O’Leary told us.
Playing a 1950s Tycoon With Star Power
O’Leary’s character, Milton Rockwell, isn’t just any businessman — he’s married to a glamorous movie star, played by Gwyneth Paltrow, and holds the keys (literally) to Timmy’s Marty Supreme’s dreams.
Marty, Chalamet’s character, is the hustler we all root for — using Rockwell’s plane, resources, and cash to chase his ping pong ambitions.
“It was surreal stepping onto sets that recreated 1952 NYC — Times Square, the Plaza Hotel — everything transported me back in time. I even got to wear a few authentic 50s watches, not just props,” Kevin shared, showing off his timepieces from the film.
Praise for Timothée Chalamet
Far from just a cameo, Kevin had lots of face time in the trailer, leaving fans intrigued about his role.
He didn’t hold back when talking about working with Chalamet:
“Timmy is incredible. Honestly, that performance is Oscar-worthy. He’s got such dedication, and it made my job as the rich, difficult guy that much more fun.”
Kevin’s admiration doesn’t stop there — he hinted that his first foray into film may not be his last.
“If this is the start, I’m definitely open to more roles. It’s a blast getting out of the boardroom and onto set.”
Behind the Scenes: Hollywood Meets Wall Street
O’Leary also described the movie sets and costumes, emphasizing the attention to detail that brought 1950s New York to life. From classic hotels to vintage watches, it was a fully immersive experience.
“The level of craftsmanship on set was amazing. It felt like stepping into a time machine,” he said.
Fans of both O’Leary and Chalamet are already buzzing about this unexpected pairing — a real-life “shark” and an indie Hollywood darling — and how their chemistry translates to the screen.
What’s Next for Kevin O’Leary?
While O’Leary’s Hollywood debut is getting plenty of attention, he’s keeping his options open. His role as a wealthy, cantankerous tycoon could just be the start of a new side hustle in film.
Stay tuned for more updates on Marty Supreme and exclusive insights from Kevin O’Leary’s journey from Shark Tank to the big screen.
Call-to-Action:
What do you think of Kevin O’Leary teaming up with Timothée Chalamet? Drop your thoughts below and tell us if you’re excited to see him play a 1950s tycoon!
