AceShowbiz - Conan O'Brien has long established himself as a standout figure in the world of award show hosting. Over the years, he has taken the stage to lead numerous ceremonies, including the prestigious 2025 Academy Awards. His approach combines sharp wit, heartfelt moments, and a knack for engaging with audiences both on and off the stage.

Discussing the preparation involved in hosting the Oscars, O'Brien revealed on a March 2026 episode of Michelle Obama's "IMO" podcast how he meticulously crafts his performance. "There are many elements to preparing for the Oscars," he explained, "You start brainstorming sketches, considering what pre-taped bits might work, and planning the production numbers. But above all, you focus on the jokes."

Testing those jokes is crucial, and O'Brien shared that one of his key strategies is to perform impromptu sets at comedy clubs. He tries to involve the audience in the process, asking them to honestly react to his material. "You say, 'If you laugh at a joke that's not good, you might convince me to include it, which could be fatal on Oscar night, so please be honest,'" he said. "Sometimes they laugh at parts where I’m not even reading a joke yet, and I find that hilarious."

Thankfully, the effort paid off. The jokes that O'Brien chose to deliver during the ceremony landed well, earning him the honor of hosting the 2026 Oscars. His years of experience and careful preparation have cemented his reputation as a master of award show hosting.

Looking back at some of his most memorable award show moments gives insight into why O'Brien is so highly regarded. Starting with the 2025 Oscars, where he couldn’t resist playfully teasing nominee Timothée Chalamet. "Timmy Chalamet is up for Best Actor tonight, you’re amazing and you look amazing. I love that suit," he quipped about Chalamet’s bold yellow tuxedo. "You will not get hit on your bike tonight."

This remark referenced an incident earlier that year when Chalamet was fined for taking a rideshare bike to the London premiere of his film A Complete Unknown. O'Brien continued poking fun at the young actor, joking about his portrayal of Bob Dylan, his youthfulness, and the complex storyline of Dune 2. Trying to smooth things over after the jokes, he added, "It’s fine, we’ll hang after this," only to acknowledge, "That was a no."

However, the 2025 Oscars were not all lighthearted. O'Brien took a moment to address the devastating wildfires that had recently impacted Los Angeles. Opening the show with a solemn tone, he said, "The people of Los Angeles have clearly been through a devastating ordeal and this needs to be addressed. In moments such as this, any awards show can seem self-indulgent and superfluous, but what I want to have us do is remember why we gathered here tonight."

He went on, "Even in the face of terrible wildfires and divisive politics, the work—the work this is about—continues. And next year, and for years to come, through trauma and joy, this seemingly absurd ritual is going to be here ... the magic, the madness, the grandeur and joy of film worldwide is going to be with us forever."

Earlier in his hosting career, O'Brien demonstrated his ability to blend comedy and creativity in other award shows. At the 2006 Emmy Awards, he began with a pre-taped sketch featuring a visit to Dunder Mifflin, the fictional office from The Office. In the sketch, O'Brien descended from the ceiling into the office, where the cast was busy working.

John Krasinski's character Jim remarked to the camera, "No, I did not have Conan O'Brien fall through the ceiling." Meanwhile, Steve Carell's Michael Scott emphasized the importance of practice, but O'Brien was distracted by Pam, played by Jenna Fischer. In a confessional, O'Brien admitted, "Pam is very attractive, no question. If I didn’t have an award show to host, I could easily see having two to three seasons of will-they-won’t-they sexual tension that ultimately goes nowhere."

In that same ceremony, O'Brien used humor to keep the show on schedule. He joked about placing beloved TV icon Bob Newhart in an airtight container with just enough air for three hours, warning the audience that if the Emmys ran even a second over time, Newhart would die. (In reality, Newhart passed away nearly two decades later in 2024.)

He also poked fun at NBC’s programming woes by parodying the song "Trouble" from The Music Man. Singing, "Well, we got trouble, my friends, yes we got trouble right here at NBC with a capital ‘T’ and that rhymes with ‘G’ as in ‘Gee, we’re screwed’," he lamented the network’s shrinking audience following the end of hits like Seinfeld and Friends.

Going further back, O'Brien hosted the Emmy Awards in 2002 with an opening sketch featuring Ozzy Osbourne, Sharon Osbourne, and their family. The sketch depicted a chaotic morning as O'Brien asked Ozzy why he overslept and wasn’t ready for the ceremony. "I’m hosting the Emmys," O'Brien reminded him, to which Ozzy replied with frustration, "I didn’t f***ing know, man. I’m not your f***ing keeper. You’re in my f***ing house."

Meanwhile, Sharon tried to resolve the situation by asking about O'Brien’s suit, only to discover it had been shredded by the family dogs. The chaos continued as O'Brien knocked on the bathroom door, where a teenage Jack Osbourne was "burning something" in the sink. Kelly Osbourne later assisted O'Brien with makeup, which led to another humorous quarrel.

Through all these moments, it’s clear that O'Brien has a unique ability to blend humor with sincerity, making him one of the most memorable hosts in award show history. From playful jabs at celebrities to heartfelt acknowledgments of real-world issues, his hosting style continues to resonate with audiences.

As the 2026 Oscars approach, fans and industry insiders alike eagerly anticipate what fresh and entertaining moments O'Brien will bring to the stage, confident in his proven talent to navigate the complexities of live award ceremonies with charm and wit.