Oscars 2025: Conan O'Brien Takes Aim at Timothée Chalamet, Karla Sofía Gascón and More in Monologue

Unsurprisingly, hosting the 2025 Oscars fit Conan O'Brien like a golden glove.

The perennially youthful 61-year-old had a plethora of topics to choose from to kick off the funny March 2 at the Dolby Theatre in Los Angeles—Best Actor nominee Timothée Chalamet channeling Bob Dylan, Emilia Pérez drama, drastic lengths to prevent aging as seen in The Substance, The Brutalist's 215-minute running time (really long movies, always a classic)—and sure enough he touched on all of it.

He started, in a pre-taped bit, by crawling out of Demi Moore in a nod to The Substance, then joked about his own lack of plastic surgery. The Best Actress nominee agreed, once O'Brien got to the stage, that their intimate interaction was indeed a bit "awkward." (See all the stars from the 2025 Oscars red carpet.)

And as O'Brien ticked through the most honored and talked about movies of the year, he acknowledged that Emilia Pérez star Karla Sofía Gascón, a history-making Best Actress nominee, was in attendance after her awards season hit a snag.

"I loved Anora, I really did," the host noted. "Yeah, true story. Little fact for you, Anora uses the F-word 479 times. That's three more than the record set by Karla Sofía Gascón's publicist." Miming an outraged rep, he exclaimed, "'You tweeted what?!'"

He followed that with a little soft-shoe tap dance, quipping, "I'm having fun."

"Karla Sofía Gascón is here tonight," he continued, and the camera finally flashed to the sanguine-looking actress, who acknowledged the mention with a little bow and prayer hands from her seat. "And Karla, if you are going to tweet about the Oscars, remember, my name is Jimmy Kimmel."

Gascón laughed as she leaned over to chat with someone in a nearby seat.

Moving on to Chalamet, who was sitting hand-in-hand with date Kylie Jenner, O'Brien complimented the actor's "amazing" buttercup-yellow Givenchy suit, assuring him, "You will not get hit on your bike tonight. Safe!"

And "Bob Dylan wanted to be here tonight," O'Brien added, "but not that badly." 

O'Brien likes to have a running ruse, and for this ceremony it was the threat of a cut to Conclave star John Lithgow looking "slightly disappointed" if an acceptance speech ran too long. (The night's first winner, Best Supporting Actor Kieran Culkin, took note.) Or, O'Brien countered, perhaps the idea of seeing one's old head shot would be enough of a deterrent, as he offered up old pics of Guy Pearce ('80s-era mullet), Zoe Saldaña (pretty adorable) and Chalamet (a sonogram image of a fetus in utero).

The host also got an assist from Adam Sandler, who pretended to be offended for being called out for dressing too casually in a sweatshirt, shorts and sneakers. On his way out of the theater, Sandler invited everyone in attendance to play 5-on-5 basketball and he offered an enthusiastic "Chalamet!" to the nominee, closing the comedic arc that began with a similarly goofy Golden Globes shout-out.

O'Brien helmed the Emmys in 2002 and 2006, but the 97th Academy Awards marks his first time steering what, at the end of the Internet-splintered day, is still Hollywood's biggest night.

In fact, the late-night talk show veteran and host of the podcast Conan O'Brien Needs a Friend had never even attended the Oscars before.

"This was the only way I could get invited," he quipped to the New York Times in a Feb. 25 interview.

But he said yes, he shared, because "to be a part of it is meaningful to me. I don’t think of it as a thankless task—even if I just do it once, and no one’s interested in me doing it again, it will have been a meaningful experience for me. My parents aren’t here to see it, but I know it would have been a huge deal to them."

His hosting gig was announced back in November, and he lost both of his parents the following month, his 95-year-old dad Thomas O'Brien and 92-year-old mom Ruth O'Brien dying within three days of each other.

O'Brien also acknowledged having to throw out the usual ba-dum-dum playbook once wild fires tore through L.A.'s Pacific Palisades and Altadena neighborhoods in January, destroying thousands of structures. He has been living in a hotel since his family was forced to evacuate from their home in the Palisades, while his longtime assistant and podcast sidekick Sona Movsesian lost her house in the Eaton fire.

“The strategy is my writers and I and the team that I’m working with at the Oscars, who are fantastic, the producers, everyone, we’ve got all of our sensors out,” O'Brien told The Hollywood Reporter toward the end of January. “I couldn’t tell you right now what the show is going to be. We have a million ideas, but which ones will we use? What’s going to be appropriate? What’s the right tone? Like I said, the tone might shift somewhat. You never know one way or the others."

Of course, that's where being in show business for almost 40 years comes in handy.

"Nothing’s in stone,” he told the NY Times less than a week before the Oscars. “I’m leaving every possibility on the table. I have choices right now, and we’ll see what happens.”

Conan O'Brien kept it classic in a simple black tuxedo to kick off the show, and keep scrolling to see the all the red carpet fashion at the 2025 Oscars:

In Schiaparelli. 

In custom Saint Laurent and Cartier jewelry. 

In custom Ralph Lauren and Stuart Weitzman heels. 

In custom Louis Vuitton and FoundRae jewelry. 

In Chanel. 

In Thierry Mugler and De Beers jewelry. 

In Prada and Tiffany & Co. jewelry. 

In Christian Dior and Tiffany & Co. jewelry. 

In Gucci, David Yurman jewelry, and Jaeger-Le Coultre watch. 

In Christian Siriano and Pomellato Jewelry. 

In Valentino. 

In custom Dior. 

In Chanel. 

In Giorgio Armani. 

In custom Tamara Ralph Haute Couture and LAGOS jewelry. 

In custom Valentino and Persol Ida sunglasses. 

In Giorgio Armani, David Yurman jewelry, IWC Watches watch and Santoni shoes.

In Dolce and Gabbana. 

In custom Loro Piana. 

In Balenciaga. 

In Zegna, Fred Leighton and Kwiat jewelry, and Omega watch. 

In custom Rachel Gilbert and Marco Bicego jewelry.

In Ashi Studio and Tiffany and Co. jewelry. 

In Dolce & Gabbana. 

In custom Louis Vuitton. 

In Alexander McQueen. 

In custom Balmain, Messika High Jewelry, and Amina Muaddi shoes. 

In Giorgio Armani. 

In Chanel.