Chelsea Handler Roasts 50 Cent’s Diddy Documentary, Jeff Bezos at CCAs

Chelsea Handler Roasts Leonardo DiCaprio Over Yacht Getaway in Monologue at Critics Choice Awards

Of course Chelsea Handler went there during the 2026 Critics Choice Awards. (She also went there, there and there.) But are you surprised?

Hosting the event for the fourth straight year, the comedian had an embarrassment of riches to work with as she kicked off awards season Jan. 4 at The Barker Hangar in Santa Monica, Calif. (See all the stars from the Critics Choice Awards red carpet.)

Chelsea started off with a little low-hanging fruit, cracking that, while Timothée Chalamet—a Best Actor nominee for his balls-to-the-wall performance as a roguish table tennis whiz in Marty Supreme—trained for seven years and Sinners star Miles Caton (an early winner for Best Young Actor) learned how to play blues guitar, Sean Penn took Cialis to rise to the occasion in One Battle After Another.

She then proceeded to invite Penn’s OBAA costar Benicio del Toro up to her hotel room.

“Stop being so selective about what you do,” Handler encouraged the Best Supporting Actor nominee, who was seated next to the film’s there-in-the-nick-of-time Best Actor lead, Leonardo DiCaprio. “I need you in more movies, in more TV shows, in room 708 at the Andaz Hotel tonight.”

“It was just like the Titanic, but worse,” she quipped, “because Jeff Bezos was there.” (DiCaprio and girlfriend Vittoria Ceretti were on a yacht with Bezos and his wife Lauren Sánchez, whose summer nuptials the actor attended, and was late getting back to California.)

Sinners led the field heading into the night with 17 nominations, including Best Picture, Best Director and Best Original Screenplay for Ryan Coogler, Best Actor (Michael B. Jordan) and Best Supporting Actress (Wunmi Mosaku), so of course it was in for a gentle ribbing.

Handler noted that blue music was “used to fight vampires,” while K-pop was used to fight demons.

And, speaking of which, “the cast of KPop Demon Hunters is here,” Handler noted. She quickly added, invoking the hot-button docuseries of the year Sean Combs: The Reckoning, which happened to be produced by her ex, “Not to be confused with Netflix’s other music movie, ‘50 Cent: Diddy Hunter.'”