Chelsea Handler slams Timothée Chalamet’s “stupid” Kylie shout-outs — calls his “winner mentality” over the top

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Chelsea Handler has zero interest in pretending she is charmed by Timothée Chalamet’s awards‑season lovefest with Kylie Jenner. The comic has been ripping into his gushy speeches and self‑congratulatory “winner” talk, arguing that the whole performance feels more like a brand campaign than a movie star coming into his own. Her critique has turned into a full‑blown referendum on how thirsty an A‑list actor is allowed to be in public before the cool factor evaporates.

At the center of it all is Chalamet’s very loud affection for Kylie, which has followed him from the Critics Choice Awards to the Golden Globes and through the Marty Supreme press tour. Handler is not just rolling her eyes at the romance, she is calling his repeated shout‑outs “stupid” and his “winner mentality” over the top, and she is using that discomfort to draw a sharp line between what she sees as real movie‑star mystique and reality‑TV‑style oversharing.

Chelsea Handler/Rhys Nicholson

How a gushy awards season turned into a roasting

Timothée Chalamet’s run through this year’s awards circuit was supposed to be a coronation, and in many ways it was. He arrived as the 30‑year‑old front man of Marty Supreme, a table tennis caper that has him chasing an Oscar while already beating names like Leonardo DiCaprio and George Clooney at the Golden Globes, and he leaned into that momentum with a confident, almost swaggering tone about his own trajectory as Chalamet, 30, continued. Onstage, he mixed that ambition with a very public romance, turning what could have been a standard victory lap into a running bit about how much he adores Kylie Jenner.

The moment that really set the tone came at the 31st annual Critics Choice Awards, where Chalamet declared his love for partner Kylie Jenner and told the room he could not have done it without her, a sentiment captured in his Critics Choice Awards. Earlier coverage of that night highlighted how he thanked her again in follow‑up comments, a pattern that continued when he mentioned Kylie in another televised acceptance, which was noted in a separate Bentley Maddox Online. For fans, it was a swoony confirmation that the relationship was serious. For Handler, it was the beginning of a running joke that quickly turned into a pointed critique.

Handler’s “stupid” verdict on the Kylie shout‑outs

Handler’s problem is not that Chalamet is in love, it is that he keeps turning his romance into a recurring awards‑show punchline. On her podcast appearance, she flatly called his Kylie references “stupid,” arguing that insisting he could not have delivered his performance without Jenner makes him sound unserious about his own craft. She zeroed in on that line, saying her main issue was Chalamet claiming he could not have done it without Jenner and pushing back with a blunt “Well, that is not true,” a reaction detailed in coverage of how Handler’s main issue. To her, that kind of line cheapens both the work and the relationship, turning a partner into a prop in a campaign for likability.

She did not stop at one offhand jab. In another segment, Handler was described as bashing his “stupid” Kylie Jenner shout‑outs at awards shows and contrasting him with what she called “real movie stars,” a category where she explicitly placed Leonardo DiCaprio while saying Chalamet is nothing like that, according to a recap of how Chelsea Handler BASHES. That comparison is doing a lot of work: she is not just annoyed, she is setting up a hierarchy where the old‑school leading man keeps his private life mostly off the podium, while the new guy cannot stop name‑checking his girlfriend.

“Winner mentality” and the Marty Supreme press tour

Underneath the eye‑rolling about romance is a deeper frustration with how Chalamet has talked about his own success. Handler has repeatedly taken aim at what she calls his “winner mentality,” a phrase that popped up as she dissected his Marty Supreme press run and the way he seemed to be manifesting trophies out loud. During an appearance on the Not Skinny But Not Fat podcast, she agreed with host Amanda Hirsch that his comments about being a winner and chasing greatness sounded over the top, a moment captured in a piece noting that appearance on the unpacked his attitude. For Handler, there is a fine line between confidence and self‑mythologizing, and she clearly thinks he crossed it.

Her critique is not happening in a vacuum. Chalamet’s Marty Supreme campaign has been unusually splashy, with stunts that include wearing matching orange outfits to the premiere with Kylie Jenner, jumping on a remix of a rap song tied to the film, and leaning into social media moments that keep his name trending, all of which were described in a breakdown of how stunts included wearing. Handler has mocked that whole approach, saying he seemed pretty serious about winning and getting acknowledged for his great acting, a tone summarized in coverage that noted Chelsea Handler Shaded for how intensely he chased that validation. In her eyes, the combination of big talk, orchestrated couple moments and constant Kylie references adds up to a campaign that is trying way too hard.

Dragging the romance and questioning what is “real”

Handler has also made it clear she is skeptical of the relationship itself, or at least of how it is being packaged. On the same podcast, she and Hirsch joked about whether the Kylie Jenner romance is a “real situation,” with Handler laughing as she asked if anyone actually understands what is going on with these people, a reaction captured in a write‑up that quoted how Handler also took became the butt of the joke. She is essentially saying the whole thing feels like a PR storyline, not a love story, which is a harsh read given how publicly Chalamet has staked his feelings.

That skepticism lands even harder when contrasted with reports that Kylie Jenner and Timothée Chalamet’s parents approve of their romance after those awards show shout‑outs, with family members said to be impressed by his talent and humble nature, as noted in a piece that folded in how Chelsea Handler Slams while also mentioning that approval. Handler, for her part, is not buying the wholesome narrative. Elsewhere in the episode, she side‑eyed the romance again, with Hirsch and Handler discussing how odd it is to watch such highly produced relationships play out in the public eye, a dynamic described in coverage that highlighted how Handler Also Side, unpacked their doubts. The message is blunt: she thinks the public is being sold a storyline, and she is not afraid to say so out loud.

The DiCaprio comparison and the “real movie star” debate

Handler’s sharpest line of attack might be the way she keeps dragging Leonardo DiCaprio into the conversation. She has repeatedly said “Leo would not do that” when talking about Chalamet’s Marty Supreme antics, using DiCaprio as shorthand for a certain old‑school cool. One recap of her comments noted how she mocked the way Timothee Chalamet promoted Marty Supreme and punctuated it with that exact phrase, captured in a piece headlined around how Chelsea Handler Mocks. For Handler, DiCaprio represents the “real movie star” who lets the work speak and keeps the thirst traps off the awards‑show stage.

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