Late-night royalty Conan O’Brien found his way to the 97th Oscars stage in his signature audacious fashion, teasing Hollywood’s brightest with his quick wit and slapstick comedic style.
O’Brien’s role as host came one year after fellow late-night host Jimmy Kimmel took his fourth crack at hosting. Many had grown critical of Kimmel due to an uncomfortable exchange with Robert Downey Jr. the year prior.
The former writer for “The Simpsons” and “Saturday Night Live” elevated the legacy of this year’s event with a masterclass in crowd work and timing, delivering punchlines both tame and controversial.
The entrance was initiated by an absurd depiction of O’Brien in his locked dressing room, crawling out of the back of a caricature of Demi Moore, whom he would humorously apologize to moments later. The visual itself drew inspiration from “The Substance,” the 2024 film for which Moore was nominated for best actress.
O’Brien notably set his sights on best actress in a leading role nominee and “Emilia Pérez” star Karla Sofía Gascón, who had recently garnered bad press for offensive tweets that began to surface.
“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,” O’Brien said.
Amid an ongoing debate about the usage of AI in media — namely, its use in both “The Brutalist” and “Emilia Pérez” — O’Brien also gave his perfectly crude and sarcastic two cents on the matter as it related to the show: “We did not use AI to make this show. We would never do that. We use child labor.”
In a playful sense, O’Brien flexed his penchant for Fred Astaire-style dancing by breaking into song with a cane and a slew of backup dancers. Making this moment all the more legendary was the sandworm from “Dune: Part Two” playing the piano and Deadpool dancing in the background in costumes.
As if this weren’t enough, O’Brien’s monologue was topped with a surprise appearance from fellow SNL alum Adam Sandler. Sandler endeared with his famous underdressed look, sporting a blue hoodie and basketball shorts. With a spotlight directed to his area, Sandler heckled O’Brien from the crowd before sauntering up to “A Complete Unknown” star Timothée Chalamet, hugging him profusely and exclaiming, “Chalamet!”
This was a callback to Nikki Glaser’s 2025 Golden Globes joke that claimed Chalamet sounded like something Sandler would say in his iconic cadence.
Other memorable moments outside of the monologue included the halfway point of the show, where O’Brien claimed, “It’s time for Kendrick Lamar to come out and call Drake a pedophile”; the return of the multi-instrumentalist sandworm playing the harp; O’Brien honoring the firefighters of Los Angeles and getting them to tell jokes from the teleprompter; and narrator Nick Offerman interrupting O’Brien by saying, “A challenge this big coming so late in one’s career must weigh on a man’s soul.”
O’Brien would double down on the Drake jab by saying he was “lawyered up,” and even take comedic fire at the great Bob Dylan by allowing LA Fire Department pilot Jonith Johnson to read a teleprompter joke.
“To play Bob Dylan, Timothée Chalamet learned how to sing,” Johnson read. “In fact, his singing was so good, he almost lost the part.”
In one exchange, O’Brien urged Offerman to stick to the script, to which Offerman obliged, calling O’Brien “one of the great comedians of our time.”
And right Offerman was with this conclusive statement, humorously intended or not, as the comedy icon reminded everyone that O’Brien sits atop the mountain with few other living great comedians.
