Chelsea Handler Opens Critics Choice Awards 2026 with Sharp Dig at Leonardo DiCaprio's Jeff Bezos Vacation

Chelsea Handler kicked off the 2026 Critics Choice Awards with a sharp and playful joke aimed at Leonardo DiCaprio, instantly setting the tone for the night and drawing loud laughs from the audience at the Barker Hangar in Santa Monica, California.
Hosting the ceremony for the fourth year in a row, Handler wasted no time during her opening monologue.
According to People, spotting DiCaprio in the crowd, she pointed him out and joked about his recent travel troubles. "Leo's here," she said, before adding that he almost missed the show because he was "trapped on a boat in St. Bart's."
She then delivered the punchline that brought the room down: "It was just like the Titanic, but worse, because Jeff Bezos was there."
The joke referenced DiCaprio's recent vacation in St. Bart's, where he was photographed spending time with celebrity friends, including Amazon founder Jeff Bezos.
Due to air restrictions in parts of the Caribbean following the US-Venezuela conflict, the actor was unable to leave the island as planned.
As a result, he missed the Palm Springs International Film Festival, where he was scheduled to receive the Desert Palm Achievement Award for his performance in "One Battle After Another."
DiCaprio, 51, took the moment in stride. Cameras caught him smiling sheepishly as the audience erupted in laughter. He is nominated at the Critics Choice Awards for the same film that earned him the Palm Springs honor he could not attend.
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
Chelsea Handler Reflects on Community Strength
Handler, 50, delivered the monologue on Sunday, Jan. 4, as the awards show aired live from Santa Monica.
The event marked the official start of awards season, with the Critics Choice Association celebrating the best films and television shows of the past year.
Film contender "Sinners" led the movie nominations, while Netflix's "Adolescence" topped the television categories, DailyMail reported.
This year's ceremony also introduced four new award categories, including Best Variety Series, Best Stunt Design, Best Casting and Ensemble, and Best Sound, reflecting the group's growing focus on behind-the-scenes talent.
The 2026 show followed a challenging year for the awards. The 2025 Critics Choice Awards were postponed twice due to devastating Los Angeles fires and were eventually held a month later than planned.
At that ceremony, Handler opened the night with a standing ovation for firefighters and spoke about community strength and gratitude.
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