Leonardo DiCaprio made it just in time to attend the Critics Choice Awards 2026, where he lost the Best Actor trophy to Timothee Chalamet for his role in Marty Supreme. DiCaprio was nominated for his role in One Battle After Another.
Hollywood’s big award night was hosted by Chelsea Handler. This was her fourth time hosting, and she made the most of it by putting some celebs on the spot. Yes, we are talking about Leo.
Chelsea Handler took a dig at Leonardo DiCaprio during the 2026 Critics Choice Awards. pic.twitter.com/Ygh5ZrB7z9
— Page Six (@PageSix) January 5, 2026
She roasted Leonardo DiCaprio and namechecked his billionaire friend Jeff Bezos during her opening piece. “Leo’s here,” Chelsea Handler said, greeting the Oscar-winning actor.
“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,” Chelsea Handler jokingly said.
The surprise strike on Venezuela on January 3, 2026, led by Donald Trump, almost put a halt to Leonardo DiCaprio’s award night roster as the 51-year-old actor was stuck on the Caribbean island of St. Barts, which happens to be 600 miles northeast of Caracas.
At the beginning of 2026, Leonardo DiCaprio was pictured near St. Barts, on a yacht alongside Amazon CEO Jeff Bezos and his wife Lauren Sanchez. Also clicked in the viral yacht pictures were retired NFL quarterback Tom Brady and DiCaprio’s 27-year-old girlfriend, Vittoria Ceretti.
Bae Leonardo DiCaprio, Vittoria Ceretti and Tom Brady were spotted on Jeff Bezos’ yacht in St Barts on Thursday (Jan 1).#LeonardoDiCaprio#VittoriaCeretti#TomBrady pic.twitter.com/bpN5m2aL57
— Daily Leo DiCaprio (@dailyleodicapri) January 2, 2026
While the Titanic star did make it to the Critics Choice Awards, he ended up being MIA from the 37th edition of the Palm Springs International Film Festival Awards Gala, where he was supposed to be honored with the Desert Palm Achievement Award for his One Battle After Another performance.
In his acceptance speech, DiCaprio said, “I’m stuck on the East Coast. I wish I were there to celebrate with all of you. I’m truly grateful to be a part of it, even from a distance.”
Due to air restrictions, bae Leonardo DiCaprio couldn’t attend The Palm Springs International Film Awards to receive his Desert Palm Achievement Award for One Battle After Another, so a pre-recorded message from him was played urging the fight to save cinema.#LeonardoDiCaprio pic.twitter.com/zLetQlI3xj
— Daily Leo DiCaprio (@dailyleodicapri) January 4, 2026
The actor is frequently pictured with Bezos and Sanchez. The trio was pictured together at the amfAR Gala last year. Leonardo was also one of the many guests at Jeff Bezos and Lauren Sanchez’s starry wedding in Venice last year. The two got married in June last year. The whopping $ 10 million wedding was headlined by celebrities such as Kim Kardashian, Katy Perry, and Oprah Winfrey, to name a few.
Back in 2021, a video of DiCaprio and Bezos went viral, in which the Amazon CEO’s then-girlfriend, Lauren Sanchez, was seen swooning over the actor. Bezos playfully teased DiCaprio with a meme on X, which he captioned, “Danger! Steep cliff. Fatal drop.” He added, “Leo, come over here, I want to show you something.”
Meanwhile, another highlight of the Critics Choice Awards was Best Actor winner Timothee Chalamet thanking his “partner” (his words), Kylie Jenner. “Lastly, I’ll just say, thank you to my partner of three years, thank you for our foundation. I love you. I couldn’t do this without you. Thank you from the bottom of my heart,” he said. Kylie was seen mouthing “I love you too” after Timothee’s speech at the award ceremony. Chelsea Handler also gave a moving tribute to Rob and Michele Reiner during the show.
DiCaprio recently found himself trending after a segment of his interaction with Don’t Look Up co-star Jennifer Lawrence went viral. In the clip, Jennifer is seen cryptically shading the actor for his dating life. The actor is known to allegedly break up with his partners after they turn older than 25.
“I’d really love seeing you to be a dad. I’m so sad that you don’t have a teenage daughter. You look great with one,” said Jennifer Lawrence, referring to his character in the film One Battle After Another. He played a father named Bob Ferguson to Chase Infiniti’s character onscreen.
