UNSINKABLE

Chelsea Handler Roasts Oscar Winner for Hanging Out on Jeff Bezos’ Yacht

Leonardo DiCaprio and his 27-year-old girlfriend spent New Year’s on a superyacht with the Amazon boss.

Chelsea Handler mocked Leonardo DiCaprio for spending New Year’s Eve aboard a half-billion-dollar superyacht with one of the richest men in the world.

The comedian opened the Critics Choice Awards in Santa Monica on Sunday night, taking aim at Hollywood’s A-List nominees. She didn’t spare Titanic star DiCaprio, who was nominated for his performance in the action thriller One Battle After Another.

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

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Handler’s comments come just a few days after DiCaprio, 51, and his girlfriend, Vittoria Ceretti, 27, were pictured spending New Year’s Eve on Bezos’ superyacht, Koru, with the Amazon billionaire and his wife, Lauren Sánchez. The 417-foot three-masted yacht features a Titanic-style statue of Sánchez on its prow.

DiCaprio was shown laughing at Handler’s remarks. The actor ran into travel issues this past weekend after bringing in the new year with Bezos on the Caribbean island of St. Barts. He failed to appear at the Palm Springs International Film Festival awards on Saturday night, as a result of the chaos that unfurled after President Donald Trump ordered American forces into Venezuela.

After airspace closures, DiCaprio was forced to send a recorded acceptance speech for the event, where he was set to be honored with the Desert Palm Achievement Award for One Battle After Another.

While DiCaprio didn’t win the Best Actor accolade at the Critics Choice Awards, the Hollywood icon represented One Battle After Another as the film was honored with Best Picture. Director Paul Thomas Anderson also took home Best Director for his latest feature.

Handler, in her opening monologue, also roasted Warner Bros. Discovery CEO and President David Zaslav, made a controversial comment about artist Nicki Minaj, and honored the legacy of director Rob Reiner.

DiCaprio and Bezos have reportedly been friends “for a while,” according to a source speaking to Page Six in 2021.

The Oscar-winning actor was among the Hollywood faces present at Bezos and Sánchez’s high-profile wedding in Venice last summer, estimated to have cost around $50 million. DiCaprio was in attendance along with Ceretti, an Italian model whom he has been dating since 2023. Ceretti and DiCaprio were spotted with Bezos, 61, and his wife, 56, in August 2025, too, on a double date in Ibiza.

DiCaprio’s frequent appearances on yachts—and his well-documented friendship with Bezos—have called into question his long history as a climate activist.

Meera NavlakhaEntertainment Reporter

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