Kevin O'Leary's $1,000 Bet Backfires as Timothee Chalamet Loses Best Actor Oscar
In a surprising turn at the 98th Academy Awards, actor Kevin O'Leary found himself out of pocket after losing a $1,000 bet on his co-star Timothee Chalamet winning the Best Actor trophy. The 71-year-old, who appears alongside Chalamet in the 2025 film Marty Supreme, was confident that the 30-year-old star would clinch the top prize for his role as Marty Mauser.
Michael B. Jordan Upsets Favourite Timothee Chalamet
However, the award went to Michael B. Jordan for his performance in Sinners, shocking many at the star-studded ceremony held at the Dolby Theatre in Los Angeles. O'Leary, who plays Milton Rockwell in Josh Safdie's film, defended Chalamet on the red carpet, telling CNN that the controversy surrounding Chalamet's comments on opera and ballet occurred after Oscar voting had closed, thus having no impact on the outcome.
O'Leary stated: '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 Pokes Fun at Chalamet
Host Conan O'Brien couldn't resist mocking Chalamet during his opening monologue, referencing the actor's recent remarks that 'no one cares' about opera and ballet. O'Brien 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 Chalamet and his girlfriend Kylie Jenner, who were seen laughing at the joke.
Oscar 2026 Winners Overview
The night was dominated by One Battle After Another, which won Best Picture and earned six awards in total, including Best Director and Best Adapted Screenplay for Paul Thomas Anderson. Key winners included:
- Best Actor: Michael B. Jordan - Sinners
- Best Actress: Jessie Buckley - Hamnet
- Best Supporting Actor: Sean Penn - One Battle After Another
- Best Supporting Actress: Amy Madigan - Weapons
- Best Original Screenplay: Ryan Coogler - Sinners
- Best Animated Film: KPop Demon Hunters
Jordan's win was a major upset, as Chalamet had been the favourite throughout the awards season. The field also included Leonardo DiCaprio for One Battle After Another, Ethan Hawke for Blue Moon, and Wagner Moura for The Secret Agent. Jordan portrayed dual roles as brothers in Sinners, a film about vampires haunting a hometown return.
Other Notable Moments and Winners
Jessie Buckley continued her successful awards run with Best Actress for Hamnet, beating out strong contenders like Emma Stone and Rose Byrne. Sean Penn was absent when he won Best Supporting Actor, while Amy Madigan took home the first award of the night for Best Supporting Actress. Ryan Coogler's win for Best Original Screenplay marked his first Oscar, and Autumn Durald Arkapaw's Best Cinematography award for Sinners was a touching highlight.
The ceremony also saw groundbreaking wins, such as KPop Demon Hunters for Best Animated Feature Film. The full list of winners underscores a competitive year in cinema, with films like Frankenstein and Sentimental Value also earning multiple accolades.
