The wildest moments from Oscars 2026

Mar 16, 2026 - 13:00

Conan O'Brien, dressed as Aunt Gladys from

The beauty of live television is that absolutely anything can happen, and nowhere is that more reliably, terrifyingly true than at the Oscars. The Academy Awards like to present themselves as the pinnacle of Hollywood elegance, and yet the ceremony has an almost proud history of producing moments that range from the benignly chaotic like the the La La Land / Moonlight Best Picture debacle to the genuinely unhinged, like Will Smith walking up on stage and slapping the hell out of Chris Rock in front of every famous person on earth.

The point is: Something is always going to happen. This year, however, was a relatively quiet night, the biggest event being the seventh-ever tie in Oscars history for Live-Action Short Film.

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Kevin O'Leary is placing bets on Kalshi

To kick things off, Kevin O'Leary, the Shark Tank businessman and supporting star of Josh Safdie's Marty Supreme, arrived on the red carpet and let everyone know he put a $1,000 bet on Timothée Chalamet winning Best Actor through the infamous prediction market site Kalshi. Unsurprisingly, this has now led to a snowball effect of people betting against Chalamet.

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Conan O'Brien as Aunt Gladys

In what can only be described as a bit that had absolutely no business working as well as it did, Oscars host Conan O'Brien took the stage dressed as Aunt Gladys from Weapons — the scene-stealing villain that earned Amy Madigan her Best Supporting Actress win — and somehow made it funnier than it had any right to be.

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The Live-Action Short Film Oscar is a tie??

In a moment that sent genuine shockwaves through a ceremony that has been running for nearly a century, the Live Action Short Film category produced just the seventh tie in Academy Awards history, with Two People Exchanging Saliva and The Singers.

SEE ALSO: 2026 Oscar winners: See full list

The chaos that followed was, frankly, perfect — when the crew from Two People took the stage for their turn at the microphone, the Academy apparently decided they had heard enough and physically retracted the mic while they were still mid-speech, which is either a massive technical blunder or the most passive-aggressive move in Oscars history.

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'Golden' Oscar speech gets cut off and sent to commercial

The Academy's increasingly aggressive relationship with the clock claimed another victim when KPop Demon Hunters' "Golden" took home Best Original Song and the accepting team, mid-speech, got unceremoniously cut off and sent immediately to commercial without so much as a courtesy pause — a noticeably harsher fate than the Live Action Short situation earlier in the night, where at least the affected parties were eventually allowed to finish their thoughts.