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It was the best dressed of times and the worst dressed of times, and the 2026 Oscars had some seriously memorable moments. The show started with a bang as host Conan O'Brien (dressed as Gladys Lilly from Weapons) got chased through the Best Picture nominations by a group of children (ICYMI, the most viral aspect of Weapons is the running children). And it was truly a wild ride from there.
From Robert Downey Jr. and Chris Evans' unfunny comedy bit to acceptance speeches being cut short, here are the cringiest moments from the 2026 Oscars.
1. Chris Evans & Robert Downey Jr. — & the 'Magic Mike' underwear.
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Yeah, let's just lead with this one. I love Chris Evans and Robert Downey Jr. more than almost all of my friends, and I'm thrilled they got to present an award together, but taking up that much time (AKA taking away time that could have gone to performances or acceptance speeches) with a bit that I didn't find funny just felt like a waste of airtime. It would have been so much more fun to see them ham it up about Avengers: Doomsday!
2. The shortened acceptance speeches.
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Speaking of time, it was just painful to see so many winners finally get their moment on the Oscar stage...and then get played off after just a few seconds. I cared way more about hearing the speeches than I did about Adrien Brody taking up a full 3 minutes to make fun of himself.
3. Sean Penn winning an Academy Award...and missing the show.
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Hopefully Sean Penn wasn't sick or something, but I can't think of any reason someone would miss an Academy Awards — especially when they're nominated! Kieran Culkin accepted the award on his behalf, but my watch party couldn't contain our surprise at the actor's absence.
4. The 'Bridesmaids' reunion bit.
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Another reunion that was oh so fun...and a little too long. Instead of having all the ladies read a joke, they could have capped it at 2 or 3. Although I'll admit throwing Jacobi Jupe into the mix was pretty funny.
A Hilarious Mention: Teyana Taylor putting Paul Thomas Anderson in a headlock.
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One moment that wasn't necessarily cringey but was memorable is when One Battle After Another won the Oscar for Best Picture; on the way to accept the award, the camera panned to Teyana Taylor and Paul Thomas Anderson — and the actress very excitedly threw her arms around the writer and director. The hug quickly turned into a headlock that made the whole internet laugh.
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