“The kid is a great kid,” the “Shark Tank” star said of his “Marty Supreme” castmate.

Kevin O’Leary lost this much money betting on Timothée Chalamet to win the Oscar for Best Actor

"The kid is a great kid," the "Shark Tank" star said of his "Marty Supreme" castmate.

By Wesley Stenzel

Wesley Stenzel

Wesley Stenzel is a news writer at **. He began writing for EW in 2022.

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March 15, 2026 10:32 p.m. ET

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Kevin O'Leary at the 2026 Academy Awards. Credit:

ANGELA WEISS / AFP via Getty

- Kevin O'Leary said he bet $1,000 on Timothée Chalamet to win the Oscar for Best Actor in a Leading Role.

- The *Shark Tank* star acted alongside Chalamet in *Marty Supreme*.

- O'Leary also said he thought his costar's controversial comments about ballet and opera wouldn't affect his chances: "He took a bum rap on that."

Kevin O'Leary bet big on his *Marty Supreme* costar at the Oscars.

The *Shark Tank* star revealed that he went so far as to wager money on Timothée Chalamet to win the Academy Award for Best Actor in a Leading Role.

"He's a really great guy," O'Leary said in a red carpet interview with *Variety*. "I just put 1,000 bucks on Kalshi walking in here that he's going to win."

Unfortunately for O'Leary, Chalamet lost the award to *Sinners*' Michael B. Jordan.

Timothée Chalamet at the 2026 Academy Awards in Los Angeles on March 15, 2026.

ANGELA WEISS / AFP via Getty

Also nominated for the honor were *The Secret Agent*'s Wagner Moura, *One Battle After Another*'s Leonardo DiCaprio, and *Blue Moon*'s Ethan Hawke.

At the start of the Oscars ceremony Sunday, Jordan had the likeliest odds to win Best Actor on Kalshi, with a 58 percent chance of victory, while Chalamet was in second place with 33 percent. The payout for O'Leary if Chalamet had won the award would have been somewhere around $3,000.

O'Leary, who portrayed the villainous businessman Milton Rockwell in *Marty Supreme*, said on the red carpet that he remained confident in Chalamet despite the backlash the young actor received for his comments about the dwindling popularity of opera and ballet.

"I know the voting stops long before that controversy happened," he said. "The kid is a great kid. He took a bum rap on that. And by the way, gave a lot of promo to opera houses and ballet."

Timothée Chalamet in 'Marty Supreme'.

O'Leary also told the outlet about why he joined the ensemble of the table tennis drama alongside Chalamet and Gwyneth Paltrow.

"I always feel you should get out of your comfort zone as often as you can, because you exercise the most important muscle in your body, your brain," he said. "I really enjoyed it. I was working with A-listers like Gwyneth, and Timmy was amazing. Even my agent said, 'Don't do this. You don't know how to act.' I said, 'Why don't I try it?'"

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O'Leary indicated that he's open to continuing his acting career. "Now I'm going to try and do one a year," he said.

*Marty Supreme* received nine nominations at the 2026 Oscars: Best Picture, Best Actor, Best Director, Best Writing (Original Screenplay), Best Casting, Best Cinematography, Best Film Editing, Best Production Design, and Best Costume Design.

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O'Leary previously told ** about his experience working with Chalamet. "His method, at least in front of me, was to get up and go find his character," he explained. "He would just do a circle around a light stand or something and just come back in character. I'm not kidding, like in character. Boom, sparks are flying off his fingertips."

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