Shark Tank' Star Says He Broke Prop Spanking Timoth

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.”