Entertainment & Celebrity News Today | 2 Min News | The Daily News Now! - Kevin O'Leary Bets on Timothée Chalamet at Oscars

Episode Date: March 16, 2026

Shark Tanks Kevin OLeary placed a $1,000 bet on Timothée Chalamet for Best Actor at the 2026 Oscars, narrowly missing out on a potential $3,000 payout. Despite the loss, OLeary remains enthusiastic about his acting career, aiming for one film per year to hone his skills. Support the show:Get a discount at https://solipillow.com/discount/dnn. Advertise on DNN:[e-mail] This is an automated, high-level news summary based on public reporting.Report issues to [e-mail]. View sources & latest updates:https://sources.thednn.ai/91b3aa0b981e6b65

You're listening to Entertainment and Celebrity News Today, powered by the Daily News Now. Shark Tank star Kevin O'Leary made a bold move at the 2006 Oscars by betting $1,000 on his Marty Supreme co-star. Timothy Shalameh to snag best actor. He placed the wager on the prediction market, Kalshi, right before the ceremony kicked off on March 15th in Los Angeles. Salome came close, but lost out to Michael B. Jordan from sinners. Jordan entered as the favorite with 58% odds, while Shalemay trailed at 33%. A win for O'Leary would have paid out around $3,000. On the red carpet, O'Leary praised Shalemay as a great talent who deserved better,

noting the voting wrapped up before any recent drama hit. He shrugged off the loss with his usual confidence. The bet stem from their time on Marty Supreme, which racked of nine nominations, including Best Picture and Best Director. O'Leary jumped into acting, despite warnings from his agent and love pushing his limits alongside A-Listers like Gwyneth Paltrow. Now O'Leary is eyeing more roles, aiming for one movie a year to keep sharpening his skills. Even with the bed bust, his Hollywood adventure is just getting started.

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