Timothee Chalamet's Marty Supreme co-star Kevin O'Leary loses a $1,000 bet after lead star walked away without the Best Actor Oscar

Timothee Chalamet'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 CNN 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.'

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

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 Michael and Jessie Buckley earned top acting prizes at the Oscars.

Jordan, 39, shocked the world at the 98th Academy Awards as he upset Timothee 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 Los Angeles.

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.

He upset the favorite throughout award season, 30-year-old Chalamet, who starred in Marty Supreme, as the field included: Leonardo DiCaprio - One Battle After Another, Ethan Hawke - Blue Moon, and Wagner Moura - The Secret Agent.

Jordan was in disbelief as he walked up to the stage and was greeted by last year's winner Adrien Brody.

Sinners is centered around two brothers who return to their hometown to start again only to discover that an even greater evil - in the form of vampires - is waiting to welcome them back. 

Jordan portrayed both brothers in the film: older and more serious twin Elijah 'Smoke' Moore in addition to younger and more cheerful sibling Elias 'Stack' Moore.

Jessie Buckley continued her winning ways as she earned Best Actress for her role in Hamnet.

The 36-year-old Irish actress beat out Rose Byrne - If I Had Legs I'd Kick You, Kate Hudson - Song Sung Blue, Renate Reinsve - Sentimental Value, and Emma Stone - Bugonia.

One Battle After Another was the biggest winner of the evening as Paul Thomas Anderson earned both Best Director and Best Adapted Screenplay. 

Meanwhile, Sean Penn was not in attendance as he earned his third Oscar.

The 65-year-old A-lister's name was announced by Kieran Culkin for the Best Supporting Actor Award for his work in One Battle After Another but he was not in the building to accept.

Amy Madigan took home the first award at the Oscars 2026 on Sunday night. 

The 75-year-old veteran actress earned Best Supporting Actress for her work in Zach Cregger's supernatural mystery horror film Weapons.

It was one of the most contentious categories of the night as she was up against Elle Fanning - Sentimental Value, Inga Ibsdotter Lilleaas - Sentimental Value, Wunmi Mosaku - Sinners, and Teyana Taylor - One Battle After Another.

Ryan Coogler finally earned his first win in the Best Original Screenplay category for his epic Sinners. 

One of the most touching wins of the night came when Autumn Durald Arkapaw won Best Cinematography for Sinners. 

The second award of the night was groundbreaking as KPop Demon Hunters earned Best Animated Feature Film.