Kevin O’Leary is sharing some behind-the-scenes insight into an infamous scene with Timothée Chalamet in 2025’s acclaimed film Marty Supreme.
The Canadian businessman of Shark Tank fame made his acting debut in the A24 ping-pong drama, in which he plays Milton Rockwell, a wealthy businessman married to Gwyneth Paltrow’s character.
O’Leary, who is also known for unabashed MAGA views, received acclaim for his role despite having little acting experience. O’Leary told TMZ that director Josh Safdie came to him because they were seeking a “real a--hole” for the part of Milton.
In an interview with CNN’s The Lead, O’Leary opened up about his acting debut and working with co-star Chalamet, specifically the paddle scene in which Milton publicly hits Chalamet’s character Marty Mauser.
When Marty crashes a party hosted by O’Leary‘s character, Milton agrees to give Marty a second chance for an upcoming ping-pong tournament in Tokyo. The only catch: Milton gets to spank Marty’s bare a-- with a table tennis paddle.
“The idea of having to spank, with a paddle... the backside of the most famous person in all of Hollywood—was that daunting?" asked CNN anchor Phil Mattingly.
O’Leary responded, “We had a stunt a--. I told Timmy, ‘I don’t have to do this to you.’ He wanted to immortalize his a--. He wanted to do something that no one had ever done before. Put his own a-- on screen, immortalize it.”
“I hit him so hard. I mean, I don’t know how he took it,” O’Leary continued, revealing that the paddle broke on the first hit. O’Leary added that he left an imprint of the paddle on Chalamet’s “rear-end.”
“It was unbelievable what he took. But what an amazing scene.”
Marty Supreme broke box-office records in its opening week. The film, about ambition, greed, and sportsmanship, is being touted as one of Chalamet’s best performances to date.
