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Conan O\u2019Brien<\/a> has proved to be the king of awards shows.<\/p>\n O\u2019Brien has hosted many award ceremonies through the years, including the 2025 Academy Awards<\/a>.<\/p>\n \u201cThere\u2019s a lot of different parts of [preparing for the Oscars], and you start thinking about different bits and what could [you] do for pre-tapes [or] what kind of production number can we have,\u201d he said on a March 2026 episode of Michelle Obama\u2019s \u201cIMO\u201d podcast<\/a>. \u201cYou\u2019re always thinking about jokes. \u2018What could the jokes be?\u2019 You really want to test them, and one of the ways to do that is to go out to clubs.\u201d<\/p>\n According to O\u2019Brien, he tried to make the audiences \u201cpart of\u201d his testing process during his impromptu comedy club sets.<\/p>\n Oscar Hosts\u2019 Best and Worst Moments Ever: 90 Years of Laughs and Gaffes<\/a><\/p>\n \u201cYou say, \u2018Look, if you guys laugh at a joke that isn\u2019t good, that might convince me to do it and then I\u2019m going to die on the Oscars, so please don\u2019t do that to me,\u2019\u201d he said. \u201cThey\u2019re laughing at the part where you\u2019re not even reading the joke. I love that.\u201d<\/p>\n Luckily, the jokes that O\u2019Brien did tell landed<\/a> and he was asked to host the 2026 Oscars.<\/p>\n Keep scrolling to revisit O\u2019Brien\u2019s best award show moments through the years:<\/p>\n March 2025<\/p>\n While hosting the Oscars in 2025, Conan O\u2019Brien couldn\u2019t resist trolling<\/a> nominee Timoth\u00e9e Chalamet.<\/p>\n \u201cTimmy Chalamet is up for Best Actor tonight, you\u2019re amazing and you look amazing. I love that suit,\u201d he said of Chalamet\u2019s yellow tuxedo. \u201cYou will not get hit on your bike tonight.\u201d<\/p>\n Chalamet made waves earlier that year when he took a rideshare bike to the London premiere of his movie A Complete Unknown, for which he was slapped with a fine.<\/p>\n O\u2019Brien kept poking fun at Chalamet, joking about his portrayal of Bob Dylan, his youth and the confusing premise of Dune 2.<\/p>\n \u201cIt\u2019s fine, we\u2019ll hang after this,\u201d O\u2019Brien added, attempting to smooth any bad blood over to no avail. \u201cThat was a no.\u201d<\/p>\n March 2025<\/p>\n Conan O\u2019Brien\u2019s debut Oscars hosting gig wasn\u2019t all about jokes, as he seriously addressed the devastating wildfires<\/a> that affected Los Angeles earlier in 2025.<\/p>\n \u201cThe people of Los Angeles have clearly been through a devastating ordeal and this needs to be addressed,\u201d he somberly said at the top of the show. \u201cIn 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.\u201d<\/p>\n He continued, “Even in the face of terrible wildfires and divisive politics, the work, which this is about, the work continues. And next year, and for years to come, through trauma and joy, this seemingly absurd ritual is going to be here \u2026 the magic, the madness, the grandeur and joy of film worldwide is going to be with us forever.\u201d<\/p>\n September 2006<\/p>\n Conan O\u2019Brien kicked off the 2006 Emmy Awards<\/a> with a visit to Dunder Mifflin, a.k.a. the site of The Office. In a pre-taped sketch, O\u2019Brien climbed from the ceiling into the paper company\u2019s office where the entire cast had been working.<\/p>\n \u201cNo, I did not have Conan O\u2019Brien fall through the ceiling,\u201d John Krasinski\u2019s Jim told the camera.<\/p>\n While O\u2019Brien asked for directions to the Emmys, Steve Carrell\u2019s Michael needed to make sure he \u201cpracticed\u201d in advance. O\u2019Brien, however, was too distracted by Pam (Jenna Fischer).<\/p>\n \u201cPam is very attractive, no question,\u201d he said in a confessional. \u201cI mean, if I didn\u2019t have an award show to host, I could easily see having two to three seasons of will-they-won\u2019t-they sexual tension that ultimately goes nowhere.\u201d<\/p>\n