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The Academy Awards are known arsenic 1 of the astir glamorous nights successful Hollywood, but let's beryllium existent — things are bound to get a small awkward.
Here are 16 awkward moments from the 2026 Oscars:
1. Sean Penn won Best Supporting Actor, and just...didn't amusement up. He near presenter Kieran Culkin struggling similar a precocious schoolhouse pupil whose radical task spouse skipped class.
ABC / Via Hulu
Here's the clip:
lol astatine Kieran Culkin's unscripted gag astir no-show Sean Penn aft helium won Supporting Actor (his THIRD Oscar)
"Sean Penn couldn't beryllium present this evening...or didn't privation to...so I'll beryllium accepting this grant connected his behalf." pic.twitter.com/L2BcB2deAq
ABC / Via Twitter: @SpencerAlthouse
2. Best Live Action Short Film was a tie, and erstwhile Two People Exchanging Saliva co-director/co-writer Alexandre Singh started giving a speech, the mic was turned off.
ABC / Via Hulu
3. As KPop Demon Hunters shaper Michelle Wong gave her acceptance code for Best Animated Feature, she was played disconnected mid-sentence.
ABC / Via Hulu
4. And arsenic if that wasn't atrocious enough, erstwhile KPop Demon Hunters won Best Original Song aboriginal successful the night, the orchestra played disconnected their acceptance code aft Ejae tried to springiness her cowriters a accidental to speak.
ABC / Via Hulu
5. Proving that nary magnitude of wealth tin marque you cool, Kevin O'Leary — aka "Mr. Wonderful" from Shark Tank — proudly showed off his $12.93 cardinal Kobe Bryant necklace (which has gone up successful worth to $19.2 million) with an further 100 carats of Tiffany & Co. diamonds and 10 carats of rubies.
Entertainment Tonight / Via Twitter: @etnow
I mean, you springiness a affluent dude ONE movie role...
John Shearer / WireImage
6. And internationally renowned filmmaker and two-time nominee Jafar Panahi had to stock the carpet with Kevin O'Leary and his nonsense.
Vanity Fair / Via Twitter: @VanityFair
7. ALSO, arsenic if his reported $400 cardinal nett worthy isn't enough, Mr. Wonderful had to marque definite helium slipped a sportbetting endorsement into his Variety reddish carpet interview.
#KevinOLeary says helium stake $1,000 connected Kalshi connected Timothée Chalamet winning Best Actor earlier walking onto the #Oscars reddish carpet:
“I cognize the voting stopped agelong earlier that contention happened. That kid is simply a large kid.”
Watch present connected CNN and TBS oregon watercourse connected the CNN app. pic.twitter.com/8mHUp8MVsa
Variety / CNN / Via Twitter: @Variety
8. Host Conan O'Brien thanked the orchestra past referenced Timothée Chalamet's spanking country from Marty Supreme. The cameras chopped close to Timmy and his girlfriend, Kylie Jenner, for their unrecorded reactions.
ABC / Via Hulu
9. Conan tried to link with Gen Alpha viewers, and... well, if you tin decode what this means successful the comments, please assistance maine out.
ABC / Via Hulu
"When you're hostmaxxing the Oscars and lowkenuinely trying to rizz up by going brain-rot mode, and adjacent though you're unc-coded with a clump of famepilled NPCs, you're inactive S-Tier level aura farming. Six-Seven."
10. On the reddish carpet, Paul Mescal had woman Gracie Abrams singing, "Where's the trophy? He conscionable comes scurrying implicit to me."
Via Twitter: @etnow
11. During the Best Casting presentation, the camera relation got a small excessively excited astir Delroy Lindo and chopped to him portion Wagner Moura was inactive speaking.
ABC / Via Hulu
12. Timothée Chalamet said "Bye Bye Bye" to reddish carpet apparel that acceptable properly.
Josh Billinson / Via x.com
Mike Coppola / Getty Images
13. Conan tried to marque his ain Leonardo DiCaprio meme.
ABC / Via Huli
I'm sorry, but erstwhile this Twitter idiosyncratic pointed this out, I couldn't not stock it with you.
ABC / Via Twitter: @juggler972
14. Presenter Matt Berry announced the ceremony's precise glamorous, precise exclusive sponsor successful a mode that lone Matt Berry could...
ABC / Via Twitter: @ditzkoff
15. Timothée Chalamet's divisive comments astir ballet and opera came backmost to haunt him.
omg here's Timothée Chalamet's absorption erstwhile Oscars big Conan O'Brien joked astir his ballet/opera comment
"Security is highly choky tonight. I'm told there's interest astir attacks from some the opera and ballet community."
[gasps from audience]
"You're conscionable huffy you left… pic.twitter.com/q7ZCZy9kmG
ABC / Via Twitter: @SpencerAlthouse
ABC / Via Hulu
16. And finally, meanwhile, Twitter reminded america that each of this was taking spot astatine the section mall.
@HollywoodComet / @KolleenCarney / Via x.com
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