Conan O’Brien came back to host the Oscars 2026 for a second straight year and honestly, the man went for it. He roasted Timothée Chalamet’s ballet and opera controversy, took shots at the Jeffrey Epstein files, mocked American health care, and even addressed the Iran war. Then the Bridesmaids cast reunited, the Avengers assembled again, and there was a TIED category for the first time in 14 years. This ceremony had everything.
While the night was full of chaos and comedy, Michael B. Jordan’s Best Actor win at the 2026 Oscars added a powerful, career-defining moment to the ceremony.
What You Should Know
- The Oscars hosted by O’Brien, Conan himself, featured a nearly 20-minute opening monologue for the second consecutive year
- He roasted Timothée Chalamet over his viral ballet and opera controversy as Kylie Jenner watched
- The Bridesmaids cast (Wiig, Rudolph, McCarthy, Byrne, Kemper) reunited on stage
- Robert Downey Jr. and Chris Evans did a mini-Avengers reunion as presenters
- The Best Live Action Short Film category ended in a TIE — first time in 14 years
- Anne Hathaway and Anna Wintour recreated a “Devil Wears Prada” moment
- Jimmy Kimmel dropped Trump jokes and took shots at the Melania documentary
Conan O’Brien Turns Oscars 2026 Into a Night of Wild Moments
Where do I even start? Conan’s monologue was a machine gun of jokes. The Chalamet roast was gold — the guy has been catching heat for saying he goes to the ballet and opera, and O’Brien Conan made everyone laugh as “Aunt Gladys,” mocking the whole thing while Kylie Jenner sat in the audience reacting.
Then the Bridesmaids cast walked out and the crowd lost it. Fifteen years since that movie and Kristen Wiig, Maya Rudolph, Melissa McCarthy, Rose Byrne, and Ellie Kemper still have chemistry that makes everyone laugh. They joked about how “well” they’ve aged. Classic stuff.
The tied category was absolute chaos. Kumail Nanjiani opened the envelope and said, “It’s a tie. I’m not joking.” The production tried to cut off one winner’s speech, the audience groaned, and Conan stepped in to rescue the moment, showing why the O’Brien Conan pairing works so well. First tie since 2013. Meanwhile, the night wasn’t just about surprises—fans were also obsessing over the best dressed Hollywood stars on the Oscars 2026 red carpet. Also, Barbra Streisand sang “The Way We Were” during the In Memoriam tribute for Robert Redford, and she had the entire room in tears.
Conan even joked about Hollywood fashion risks, taking a swipe at Gwyneth Paltrow’s Oscars dress nearly causing a wardrobe malfunction during his monologue.
What’s Next
Conan might be locked in as the permanent Oscars host at this point. Two years running and the ratings are reportedly solid. As a result, there is more speculation about O’Brien Conan staying on for a third round. Whether he comes back for a third round remains to be seen, but Hollywood clearly loves what he’s doing. And that Bridesmaids sequel? After that reunion, the pressure just got turned up to eleven.
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