
Kevin O’Leary is a well-known businessman, crypto evangelizer, Donald Trump enthusiast and “mean judge” on NBC’s Shark Tank. So, yes, he’s busy enough. But somewhere between trips to Mar-a-Lago and cable news appearances, he found time to shoot a movie. And not just any movie: a super-buzzy, high-budget Oscar contender co-starring Timothée Chalamet and Gwyneth Paltrow.
This is not a cameo. Marty Supreme is set in the 1930s and based on the real-life story of a ping-pong whiz kid (played by Chalamet). O’Leary is fourth on the call sheet. His character, Milton Rockwell, seems to be based on a real tycoon and is married to Paltrow’s character. In the trailer, he’s positioned as the bad guy who gets a kick out of crushing dreams. If you’re thinking, Well, that sounds like some pretty on-the-nose casting, you are not alone.
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Back in August, O’Leary told TMZ that he’d been approached by director Josh Safdie, who had said, “We’re looking for a real a**hole, and you’re it.” Safdie has confirmed the story in a new Hollywood Reporter interview that coincided with the film’s surprise world premiere at the New York Film Festival on Monday. “I needed someone who you did not like, and did not like in a deep, unconscious way,” Safdie said. “I looked at a lot of real businessmen and people who have no history of being on camera. Kevin in particular on Shark Tank is always the guy who’s going to be an asshole. But that’s what’s so fun about him—you enjoy watching him be a dick.”
Did O’Leary have to take acting lessons? Of course not—he’s spent the past 50 years method-acting this part to perfection. And based on the reviews that are rolling in, the decades of practice were well worth it. All of which is to say: yes, Mr. Wonderful will almost certainly be a red-carpet fixture come awards season.
Let the race for best supporting [expletive] begin!
Courtney Shea is a freelance journalist in Toronto. She started her career as an intern at Toronto Life and continues to contribute frequently to the publication, including her 2022 National Magazine Award–winning feature, “The Death Cheaters,” her regular Q&As and her recent investigation into whether Taylor Swift hung out at a Toronto dive bar (she did not). Courtney was a producer and writer on the 2022 documentary The Talented Mr. Rosenberg, based on her 2014 Toronto Life magazine feature “The Yorkville Swindler.”