Kevin O’Leary Talks Playing a “Real A*hole” in Timothée Chalamet’s New Movie

Kevin O’Leary is making the jump from Shark Tank to the big screen — and he admits his latest role might be a bit of typecasting.

The investor stars in the upcoming Timothée Chalamet film Marty Supreme, where he plays Milton Rockwell, one of America’s richest men in 1952. Speaking on TMZ Live, O’Leary said the film’s director and writer specifically approached him to play “a real a***hole,” and he was happy to take it on.

In the movie, Rockwell is married to a glamorous film star played by Gwyneth Paltrow. Chalamet’s character, Marty Supreme, is a hustler with big dreams of becoming a ping pong champion — and he needs Rockwell’s private plane and money to make it happen.

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O’Leary said filming on location at spots like Times Square and The Plaza Hotel truly transported him back to 1950s New York. He even wore authentic luxury watches from the era — not just movie props — during his scenes.

The Shark Tank star had nothing but praise for “Timmy” Chalamet, calling his performance Oscar-worthy, and said working alongside him was a highlight. As for whether this marks the start of an acting career, O’Leary didn’t rule it out, hinting that more movie roles could be on the horizon.

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