This article contains mentions of pedophilia, racism, and sexual assault.
Conan O’Brien hosted the 2025 Oscars, offering up many jokes that pushed the limits and leaned into controversial topics. The Oscars are the most-anticipated event of the year for Hollywood, and the 2025 show was the best in years. I could feel the love and appreciation that the participants had for the art of making movies. The night included some genuine surprises, such as Flow’s Best Animated Movie award. Additionally, one of the biggest factors that contributed to the success of the 2025 Oscars was Conan O’Brien hosting the event.
As the host of two late-night talk shows, Conan O’Brien’s speaking abilities and humor aren’t anything new. He has a charisma that draws audiences in. However, I still found myself deeply impressed by O’Brien’s willingness to take risks with his jokes while hosting the Oscars. Though he included some lighthearted jokes in the Oscars’ opening monologue about Timothee Chalamet’s yellow suit and Jeff Bezos’ Amazon package getting stolen, he also wasn’t afraid to dole out some deep jabs that few others would get away with.
6 The Joke About Gascón’s Tweets
Conan O’Brien Layed Into Karla Sofía Gascón In The Oscars Intro Monologue
One of the funniest Conan O’Brien jokes that lean into controversy is his prolonged bit about Karla Sofía Gascón’s tweets. At the end of January, old tweets from Gascón resurfaced, expressing racist and Islamophobic sentiments, including victim-blaming George Floyd and degrading former Oscar winners. The movie Emilia Pérez was already in controversy before Gascón’s bigoted tweet resurfaced, but the lead actress’s social media history might have ruined the movie’s chance at gaining more awards. Despite having the most nominations of the night, Emilia Pérez only took home two out of their 12 possible awards. O’Brien said this during his monologue:
“Little fact for you: Anora uses the F-word 479 times. That’s 3 more than the record set by Karla Sofía Gascón’s publicist. ‘You tweeted what?!’ Karla Sofía Gascón is here tonight, and, Karla, if you are going to tweet about the Oscars, remember, my name is Jimmy Kimmel.”
While most of the other controversial jokes were either directed at a group or made at the expense of people not present, Karla Sofía Gascón sat in the audience watching the digs at her. The jokes about Gascón were probably planned with the thought that she wouldn’t show up. The likelihood of her appearing seemed slim after she missed the BAFTAs and the Oscars Red Carpet.
5 The Brutalist AI Joke
Conan O’Brien’s AI Joke Took A Jab At Both The Brutalist And The Child Actor Industry
In Conan O’Brien’s opening monologue for the 2025 Oscars, he made many jokes about the individuals and movies nominated for awards this year. One of the jokes served primarily as a dig at The Brutalist, a movie nominated for Best Picture, using AI in their film.
The movie landed in hot water after editor Dávid Jancsó shared that the creative team used generative AI to make Felicity Jones’s and Adrien Brody’s accents sound more authentic when they spoke Hungarian. Rumors have also floated around about the blueprints and buildings using AI, though director Brady Corbet denies those allegations to Vanity Fair. During Conan O’Brien’s speech, he said this:
“Before we go any further, we did not use AI to make this show. No AI. We would never do that. We used child labor. Hey, they’re still people!”
Other than the apparent commentary about AI usage, his joke also seems to include a second layer that’s equally controversial. The ending of his joke comes across as a dig at the ongoing problem with child actors in Hollywood. In the last few years, many child actors have shared their troubling experiences in the business, raising conversations surrounding the ethics and safety. The doubled layer of the joke makes it even funnier and more brilliant than it would’ve been if he had ended it with the part about not using AI.
4 The Joke About The Catholic Church Scandal
Conan O’Brien Reassures Viewers That Conclave Isn’t THAT Kind Of Catholic Church Movie
One of the nominees for the 2025 Oscars was the movie Conclave – a dramatic thriller about a member of the clergy named Cardinal Lawrence (Ralph Fiennes) who’s tasked with running the secretive process of picking the next pope along with the Church’s most senior members. During the opening monologue, Conan O’Brien drops a hilarious, albeit edgy, joke about the previous films centered around the Catholic Church. He said, “The movie Conclave is up for Best Picture tonight. If you haven’t seen Conclave, its logline is, ‘A movie about the Catholic Church…but don’t worry!’”
Most Oscar-nominated films about the Catholic Church, like Doubt (2008) and Spotlight (2015), center on storylines of sexual abuse. Though they fictionalize the controversy, these films have continued to portray deep, disturbing truths that reflect negatively on the Church. The Conan O’Brien joke simultaneously acknowledges the past trend while quelling the nerves of potential viewers who might get concerned about the film. Unlike its predecessors, Conclave doesn’t have any earth-shattering revelations about the clergy members acting in evil ways. Additionally, the joke feels more lighthearted than others because it isn’t picking on a single individual but an institution.
3 The Joke About Bob Dylan’s Singing Voice
Conan O’Brien’s Joke About Bob Dylan Will Ruffle Some Feathers With Fans
One of the controversial jokes that is least likely to shock or offend people relates to A Complete Unknown, Timothee Chalamet, and Bob Dylan. A Complete Unknown had Timothee Chalamet sing all of Bob Dylan’s songs throughout the filming, giving the movie a degree of authenticity that many musical biopics lack. However, he faced a challenge – learning to sing like Bob Dylan, who has a distinctive voice. Conan O’Brien instructs a firefighter to read the teleprompter, which says, “To Play Bob Dylan, Timothee Chalamet learned how to sing. In fact, the singing is so good, he almost lost the part.”
RelatedWhile there were not too many surprising parts of the 97th Academy Awards, a select handful of wins were truly stunning, especially for Best Actress.
While it might surprise some readers, I’ve learned through my research and coverage of A Complete Unknown that the debate about Bob Dylan’s singing voice is alive and well in the year 2025, with people arguing strongly on both sides. As such, it’s much more controversial than it seems to the casual viewer. Ultimately, a firefighter might have delivered the line, but it has the tone, wit, and timing of a Conan O’Brien joke. It reads like the comedian wrote the jab, so I’ve made the judgment call to include it.
2 The Drake-Kendrick Lamar Feud Joke
Conan O’Brien Hits Hard At Drake Halfway Through The 2025 Oscars
At the halfway point in the Oscars, Conan O’Brien delivered what is one of the 2025 Oscars’ most memorable jokes. He said, “Well, we’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile. Don’t worry, I’m lawyered up.” This is a very overt reference to the ongoing feud between the two rappers, leading to Kendrick Lamar’s incredible Super Bowl halftime performance and Drake’s lawsuit. The two rappers started out as collaborators but began feuding sometime around 2013. The issue became more prominent in 2024 when they started trading diss tracks back and forth.
During Super Bowl LIX, Lamar gave a powerful halftime show, which included the Grammy Award-winning diss track “Not Like Us.” The lyrics include the line, “Certified Lover Boy? Certified pedophile.” This references allegations against Drake about him having a relationship with girls, which he has denied. The choice to include this song in the halftime show was bold, considering Drake filed a defamation and harassment lawsuit because of “Not Like Us.” This litigious nature is why O’Brien mentions being lawyered up at the end of the joke.
1 The Joke About Anora Standing Up To Russians
Conan O’Brien Gives A Verbal Gut Punch To Trump
Most of Conan O’Brien’s jokes kept the political messaging as subtext, except for one – the Anora joke. Part of the way through the awards show, O’Brien gives praise to Anora, the film that won the most 2025 Oscars, for its successes. The movie follows a young sex worker named Ani who impulsively marries a billionaire Russian man. When his parents try to force them into an annulment, she must fight back against them to keep her money.
RelatedAs per usual, all kinds of records were broken at the 2025 Oscars. So, here is a full breakdown of each record that was broken at the Academy Awards.
During the speech, O’Brien says, “You know, Anora is having a good night. That’s Great. Two wins already. I guess Americans are excited to see somebody finally stand up to a powerful Russian.” His deadpan expression afterward makes the already-hilarious joke even funnier. This is an obvious slam against Donald Trump that will piss off the MAGA crowd. The leader is known for his close relationship with Vladimir Putin, calling the backlash against the Russian leader a “witch hunt” (via The Independent). Viewers quickly labeled the Anora joke the best of the Oscars 2025, and I couldn’t agree more.
