Kevin OLeary Loses $1,000 Bet on Chalamet

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's Marty Supreme co-star Kevin O'Leary lost a $1,000 bet after the lead star walked away without the Best Actor trophy at Sunday night's Oscars.

The 71-year-old actor, who appears as Milton Rockwell in Josh Safdie's 2025 film, was certain Timothee - who played Marty Mauser - was going to scoop the top prize for the role.

But Timothee, 30, lost out to Sinners star Michael B. Jordan in the end at the star-studded ceremony.

Kevin noted at the event how Timothee's opera and ballet controversy happened way before voting closed so that would have no impact on his chances as he defended him following the comments. 

Speaking to on the red carpet at the bash, Kevin said: 'He's a really great guy...

'I just put 1000 bucks on Kalshi walking in here that he's going to win, because I know the voting stops long before that controversy happened. 

'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.'

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Host Conan O'Brien couldn't resist poking fun at Timothee as he opened the .

During his opening monologue he took a playful swipe at the star's recent comments that 'no one cares' about the art forms.

He quipped: 'Security is very tight tonight. There's concerns about attacks from the ballet and opera communities. They're just mad you left out jazz.'

The camera cut to Timothee and his girlfriend Kylie Jenner, and he was seen laughing at the jibe.

One Battle After Another ended the 2026 awards season by winning Best Picture on a night where  and earned top acting prizes at the Oscars.

Jordan, 39, shocked the world at the 98th as he upset  to win Best Actor for Sinners as Buckley, 36, took home Best Actress for her work in Hamnet at the event held at the Dolby Theatre in .

Paul Thomas Anderson accepted the top prize of the night alongside Teyana Taylor and the rest of the cast and crew as the film earned the most wins of the night with six. 

The American black comedy action-thriller film triumphed over a massive, competitive, field including: Bugonia, F1, Frankenstein, Hamnet, Marty Supreme, The Secret Agent, Sentimental Value, Sinners, and Train Dreams.

The Leonardo DiCaprio-led film One Battle After Another is centered around a group of ex-revolutionaries who reunite to rescue the daughter of one of their own as their enemy resurfaces after 16 years.

The most talked about moment of the night will surely be that Jordan earned the top honor Best Actor for his leading role in Ryan Coogler's film Sinners.

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