Timothée Chalamet's Oscars loss costs Kevin O'Leary $1K

'Marty Supreme' co-star Kevin O'Leary loses Oscar bet

By TCP News Desk March 16, 2026
Timothée Chalamet's Oscars loss costs Kevin O'Leary $1K
Timothée Chalamet's Oscars loss costs Kevin O'Leary $1K

Kevin O'Leary bets against Timothée Chalamet and loses the bet when the latter loses the Oscar.

The Canadian businessman and TV personality has lost his grand to believing in his Marty Supreme co-star.

The 71-year-old actor believed that the American-French actor would become the winner of Best Actor on Sunday at the Oscars so much that he bet $1,000. 

Michael B. Jordan received the trophy instead as Sinners.

In an interview with CNN at the red carpet, O'Leary dismissed the point that the recent opera and ballet remarks by the 30-year-old potentially damaged his fortune. 

He remarked at the moment, "I know the voting stopped long before that controversy happened."

The comments made by Kylie's beau when he said that no one cares about the art forms are a good joke that was used throughout the ceremony. 

Host Conan O'Brien joked of being attacked by the ballet and opera circles, and saying they were simply unhappy you did not include jazz.

In the shot, captured by the camera, Chalamet and his girlfriend, Kylie Jenner, were laughing at the jab.

On a 2025 film Marty Supreme by Josh Safdie, O'Leary stars next to Chalamet, where the younger star portrays Marty Mauser. 

Although he lost the bet, it still indicates that O'Leary is confident of the future of his co-star.