From stage crashes to slaps heard 'round the world, award shows have given us no shortage of unforgettable cringe. Join us as we count down the most awkward award show moments of each year since 2000!

#KevinOLeary says he bet $1,000 on Kalshi on Timothée Chalamet winning Best Actor before walking onto the #Oscars red carpet:“I know the voting stopped long before that controversy happened. That kid is a great kid.”Watch now on CNN and TBS or stream on the CNN app. pic.twitter.com/8mHUp8MVsa

After a rare Oscars tie for winners, an awkward moment arrived on stage which amused host Conan O'Brien and viewers.

The content creators were tapped to host the red carpet for the Vanity Fair Oscars Party.

The 2026 Academy Awards delivered the usual mix of glamour and celebration, but the ceremony also produced several awkward and unexpected moments that quickly circulated online. One of the earliest came when Sean Penn was announced as Best Supporting Actor but did not attend the ceremony.

From the Bridesmaids reunion to Robert Downey Jr. and Chris Evans, the best and awkward presenter gags from the 2026 Oscars.

"The Great British Baking Show" is known for being slow, gentle TV. Contestants help each other out, and nobody talks to the camera about how they're going to crush the opposition. But "The Great British Baking Show" has had its share of awkward moments.

The 31st Annual Critics Choice Awards officially kicked off the 2026 awards season with a night that balanced prestige film making with the kind of unhinged, viral energy only Chelsea Handler can deliver. Hollywood descended upon the Barker Hangar in Santa ...

The Academy Awards will never get past their inherent tedious contradictions. So enjoy the ceremony for what it is, while it lasts.