Chelsea Handler Hilariously Roasts Leonardo DiCaprio for Yachting with Jeff Bezos at Critics Choice Awards 2026

Chelsea Handler kicked off the Critics Choice Awards 2026 with a funny jab at Leonardo DiCaprio. The comedian, who hosted the event for the fourth year in a row, made the joke during her opening monologue on Sunday, Jan. 4, at the Barker Hangar in Santa Monica, California.

“Leo’s here,” Handler said, pointing to the 51-year-old actor in the audience. “Thank God. Leo almost didn’t make it tonight because he was trapped on a boat in St. Bart’s. It was just like the Titanic, but worse, because Jeff Bezos was there.” The crowd laughed loudly at the remark.

Chelsea Handler roasts Leonardo DiCaprio for being stuck on a boat in St. Barts: “It was just like the ‘Titanic’ but worse because Jeff Bezos was there.” #CriticsChoiceAwards pic.twitter.com/wjjAzogkcw

— Variety (@Variety) January 5, 2026

Handler’s joke referred to DiCaprio’s recent vacation in St. Bart’s with friends, including the billionaire, which left him unable to attend the Palm Springs International Film Festival due to air restrictions in the Caribbean after the U.S.-Venezuela conflict. At the festival, DiCaprio was set to receive the Desert Palm Achievement Award for his role in One Battle After Another, for which he is also nominated at this year’s Critics Choice Awards.

This year, the ceremony highlighted the best movies and TV shows of the past year. Sinners led the film categories with 17 nominations, while Netflix’s Adolescence topped the TV nominations with six. The Critics Choice Association also introduced four new awards this year: Best Variety Series, Best Stunt Design, Best Casting and Ensemble, and Best Sound.

The 2026 ceremony follows a challenging 2025 event, which was postponed twice due to the devastating Los Angeles fires in January.

When the delayed ceremony finally took place in February, Handler and the audience gave a standing ovation to firefighters and volunteers. Handler said at the time, “My hope for tonight is to take our time here together, and use it to remind each other and everyone watching of the resilience and determination that is within all of us when we come together as a community, with a huge debt of gratitude to our honored guests tonight, the firefighters, Red Cross and Habitat for Humanity volunteers.”

Handler’s mix of humor and respect for serious issues once again set the tone for a memorable night of awards.

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