Chelsea Handler Shades Timothée Chalamet’s Latest Hollywood Moment

Chelsea Handler is never one to bite her tongue, and Timothée Chalamet just became her latest target. The comedian hopped on the "Not Skinny But Not Fat" podcast and didn’t waste time weighing in on Chalamet’s latest "Marty Supreme" press tour, questioning whether the actor has been taking the whole awards-season moment a little too seriously. And that wasn’t the only topic she had opinions on. Chelsea Handler also dove into Timothée Chalamet’s very public romance with Kylie Jenner, calling one of his recent shoutouts “ridiculous” and admitting she’s still not convinced what’s really going on with the couple.

Chelsea Handler Targets Timothée Chalamet’s ‘Marty Supreme’ Press Tour

Handler blasted Chalamet’s "Marty Supreme" press tour on the podcast on Tuesday, January 13. When host Amanda Hirsch asked whether the actor took the promotion “too seriously,” Handler agreed. “It seems so.”

The 50-year-old explained what stood out to her about Chalamet’s approach. “He seemed pretty serious about winning and getting acknowledged for his great acting," she added.

While Handler clarified she does believe Chalamet is “a great actor,” she also admitted the tone can be a lot. “It’s hard to hear someone talk about how great they are at acting," the comedian said.

Handler Also Side-Eyes Chalamet’s Kylie Jenner Romance

Elsewhere in the episode, Hirsch and Handler discussed Chalamet declaring his love for his girlfriend, Kylie Jenner, during his acceptance speech at the Critics’ Choice Awards 2026. The comedian, who hosted the January 4 awards show, admitted she’s still confused by the relationship. “I don’t understand what that situation is," she revealed. "Is that a real situation? Are they in love? Are they a couple?”

After Hirsch explained why Chalamet’s public shoutout was a major deal for fans, she brought up one particular line in his speech: “I couldn’t do this without you.” Handler wasn’t buying it, calling this “ridiculous” and “stupid” because “obviously he could do [his career] without” Jenner.

The former "Chelsea Lately" host shrugged off the excitement surrounding the couple, adding, “I don’t know what’s f-cking going on with these people, OK?”

Chelsea Handler Calls Tom Brady A 'Total Dud' Amid Alix Earle Rumors

Handler has also been making headlines for her brutally blunt take on a very different celebrity topic, none other than Tom Brady’s rumored romance with TikTok star Alix Earle. The pair fueled rumors while ringing in the New Year in St Barts, where they were spotted getting cozy at an ultra-exclusive beach party surrounded by celebrity friends. Videos showing Earle rubbing Brady's back and the NFL commentator pulling her in by the waist quickly went viral, sparking intense online speculation.

While appearing on SiriusXM’s Page Six Radio, the comedian didn’t hold back when asked about the buzz surrounding the retired NFL star and the 25-year-old influencer, delivering a scathing assessment of Brady’s appeal. “I have no interest in Tom Brady. I don't find him dynamic, hot, interesting, or fun. Like, and I don't, I find him so boring,” Handler said.

She then doubled down, adding, “I think he's a total dud. I couldn't, I mean, so I don't have any thoughts, and I don't really know that enough about Alix Earle. So, I don't care to answer your question. Do I need to expound?”

Handler Roasts Leonardo DiCaprio After He Nearly Missed Critics Choice Awards

Handler also made waves during her hosting gig at the 2026 Critics Choice Awards, and Leonardo DiCaprio found himself in her line of fire. During her opening monologue at Santa Monica’s Barker Hanger on January 4, the comedian ran through the night’s biggest nominees and kicked things off with DiCaprio, who stars in one of the year’s most talked-about films, “One Battle After Another.”

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

Just days before Handler’s joke went viral, DiCaprio and his girlfriend, Vittoria Ceretti, were spotted in St. Barts aboard a superyacht with Jeff Bezos and Lauren Sánchez. Although the actor did make it to the Critics’ Choice Awards, he was notably absent from the Palm Springs International Film Festival Awards Gala the night before, after being unable to fly due to FAA air traffic control issues in the aftermath of the attack on Venezuela.

Chelsea Handler Takes Aim At Warner Bros. CEO David Zaslav With ‘Sinners’ Joke

Handler didn’t stop with Leonardo DiCaprio. She also took a sharp swipe at Warner Bros. CEO David Zaslav while referencing the blockbuster hit “Sinners.”

“‘Sinners’ is the story of brothers who start this really fun place for entertainment, and then vampires show up, suck the life out of everybody and burn it all to the ground,” she began. “Fun fact, the original name of the main vampire was David Zaslav.”

From awards-season shade to celebrity romance rumors, Handler’s latest commentary continues to make headlines.