Leo DiCaprio Reacts to Chelsea Handler’s Critics Choice Monologue Yacht Joke

Host Chelsea Handler brought the laughs to the 2026 Critics Choice Awards with her rousing monologue — and even left Jean Smart speechless.

The comedian, 50, kicked off the Sunday, January 4, awards show at Barker Hangar in Santa Monica, California, with jokes about the film and television industry. Handler did not hold back when calling out several stars, but Leonardo DiCaprio took it on the chin — and even seemed to enjoy it — when his name came up.

“Leo’s here, thank God,” Handler quipped. “Leo almost didn’t make it tonight because he was trapped on a boat in St. Barts. It was just like the Titanic, but worse, because Jeff Bezos was there.”

DiCaprio, who is nominated for his movie One Battle After Another, could be seen laughing as the camera focused on him. While discussing the same film, Handler noted that her “p**** absolutely pops” for Teyana Taylor. The comedian also hit on the film’s star Benicio del Toro.

“Benicio, you’ve had a phenomenal year this year, and we need to see more of you, OK?” she said. “Stop being so selective about what you do. I need you in more movies, in more TV shows, in room 708 at the Andaz Hotel tonight.”

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Handler also made her traditional jabs, even taking at shot at Nicki Minaj‘s political affiliation, “White Hollywood” and the feud between Kevin Costner and Taylor Sheridan. She hilariously referred to Timothée Chalamet as “a labubu” and on the more relatable end, praised Jacob Elordi‘s height. (He comes in at a tall 6-foot-5, ladies.) Things also took a more somber turn when Handler brought up the recent death of director Rob Reiner before starting to hand out awards. (Rob’s son Nick has been arrested and charged with the death of the director and his wife, Michele Reiner.)

“Everyone in this room knows that the nicest guy in Hollywood was Rob Reiner,” she said. “Anyone who ever spent time with Rob Reiner knows that the minute that you met him, he felt like an old friend. When you were in a conversation with him, he was present, focused and funny and asked you tons of questions.”

This marked Handler’s fourth consecutive year hosting the Critics Choice Awards, which gives critics and journalists the opportunity to honor achievements in film and television.

“Chelsea Handler is the best awards show host in the world,” Critics Choice Association CEO Joey Berlin said in a November 2025 press release. “We are absolutely thrilled to have her back on our stage, mixing her trademark mix of humor and heart in front of hundreds of stars who enjoy her as much as we do. Recognizing and celebrating the most deserving achievements in film and television is important, but it’s also great fun and Chelsea is the perfect person to lead the parade.”

Handler added in her own statement: “Kicking off the year with the Critics Choice Awards feels right — nothing says ‘new beginnings’ like a room full of critics ready to tell you how you did last year.”

Since making her Critics Choice Awards hosting debut in 2023, Handler has made headlines for her jokes at the ceremony on more than one occasion. During the 2025 broadcast, she made light of Blake Lively and Justin Baldoni’s It Ends With Us legal drama.

“I want to acknowledge that we’ve been through a lot lately, not just here in Los Angeles, but our entire country,” she said in her monologue at the time. “It is important in times like these to have a distraction and that’s why I want to personally extend my gratitude to Justin Baldoni and Blake Lively. Thank you for providing us with that distraction. I’m grateful; I think we’re all grateful and I think we’re good.”

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“I think everyone in the room, no matter whose side you’re on, we can all agree to accept that there’s probably not going to be a sequel,” she added. “It ends with us, guys.”

One year later, Lively, 38, and Baldoni, 41, are still awaiting the trial — which is scheduled to begin in May — concerning her December 2024 lawsuit that accused him of sexual harassment and a smear campaign against her, which he has denied.

As for Handler, she opened up about her ongoing personal evolution shortly after hosting the 2025 Critics Choice Awards.

“You want to get rid of the bad behavior that’s hurtful to others or hurtful to yourself, and also adopt this new version of you,” she exclusively told Us Weekly in her February 2025 cover story. “I don’t want to lose all the edge I was naturally born with — that’s who I am — so it’s a bit of Whack-a-Mole. You’re like, OK, I’m auditioning different versions of myself, seeing which ones make the most sense for this improved version of me.”