From post 9/11 tributes to accidental wins and awkward hosting gigs, the Academy Awards has delivered its fair share of unforgettable moments. This article looks back at eight of the most unexpected Oscar nights from the 21st century.
With Los Angeles still recovering from devastating wildfires and the Oscars race thrown into disarray following a controversy centered on Emilia Pérez’s Karla Sofía Gascón, it's a wonder that the 2025 Academy Awards are still proceeding. The ceremony faces the daunting task of balancing entertaining a largely disengaged and shrinking television audience while remaining sensitive to the challenges faced by the host city.
It will also have to navigate the awkwardness of its top nominee now being tainted by scandal, an event we'll likely all be watching through our fingers. Still, even all of that might not make it the weirdest Academy Awards ceremony ever. Below, we delve into eight unforgettable Oscar nights from the 21st century, each delivering unexpected moments. 2002: A Post 9/11 Love Letter to New York Six months after the September 11 attacks, many suggested postponing or canceling the Oscars. However, the Academy persevered, with then-president Frank Pierson declaring in Variety that, “If we give in to fear, if we aren’t able to do these simple and ordinary things, the terrorists have won the war.” The show went ahead with heightened security, and Tom Cruise opened the ceremony, asking the audience: “Should we celebrate the joy and magic that movies bring? Dare I say it, more than ever.” The evening featured a moving tribute to New York and a plea for filmmakers to continue working there, followed by a sweeping montage curated by local hero Nora Ephron. 2003: The Iraq War Divides the Room Just a year later, the mood shifted from somber solidarity to deeply divisive. Bizarrely, the 75th Academy Awards took place only three days after the surprise US invasion of Iraq. Hours after the news broke, several Oscar presenters, including Cate Blanchett and Jim Carrey, stepped down. ABC, the show's broadcaster, requested a postponement, but the Academy refused citing logistical issues. The usual red-carpet fanfare was significantly toned down, with news updates delivered during commercial breaks. (Truth be told, most viewers were glued to live coverage of the war, resulting in the Oscars achieving its lowest viewership up to that point.) Then came the moment that finally pierced the veil between the oblivious Hollywood fantasy and the horrifying reality unfolding on the news: Michael Moore accepting his Best Documentary Feature Oscar for Bowling for Columbine and condemning then-President George W. Bush. “We live in a time where we have fictitious election results that elect a fictitious president,” he told the audience. “We live in a time where we have a man sending us to war for fictitious reasons… We are against this war, Mr. Bush! Shame on you, Mr. Bush!” The result was a mixture of boos and thunderous applause. 2006: Crash Crashes the Party How on earth did Crash, of all things, win the Best Picture Oscar over – wait for it – Munich, Good Night, and Good Luck, Capote, and Brokeback Mountain? Presenter Jack Nicholson’s reaction said it all. When he opened the envelope, his face betrayed a flicker of concern, followed by a bewildered, “Woah,” mouthed to someone backstage, after announcing the victor. This decision remains one of the most perplexing in Oscars history. 2011: The Weirdest Oscars Hosting Duo of All Time In an attempt to attract a younger audience, Anne Hathaway and James Franco were hired to host the 83rd Academy Awards. It was, well, a bit of a disaster. She was wide-eyed and earnest, while he was stiff and low-energy. From the cringe-worthy opening monologue to the fumbled mid-ceremony announcements, it was an excruciating watch. There have been plenty of terrible Oscar hosts over the years, but this was a car crash that could easily have been avoided. 2017: Moonlight versus La La Land It made for eight agonizing, awkward, and ultimately joyful minutes. First, Bonnie and Clyde’s Faye Dunaway and Warren Beatty took the stage to present Best Picture. He looked at the winner’s card with confusion, double-checked the envelope, and searched for assistance. She giggled at him as if he were performing a bit before taking the card herself and announcing, “La La Land.” It seemed logical – Damien Chazelle’s dreamy musical had already won six awards. The cast and crew took the stage, delivered emotional speeches, and throughout, Beatty remained visibly troubled. As producer Marc Platt approached the microphone, fellow winners Jordan Horowitz and Fred Berger exchanged glances. Officials with headsets appeared to check the envelope. Berger shouted out his family and colleagues before saying, “We lost, by the way.” Horowitz then uttered the immortal words, “There’s a mistake. Moonlight, you guys won Best Picture,” before holding up the correct card for everyone to see.
Oscars Academy Awards 21St Century Film Entertainment History Controversy Best Picture Moonlight La La Land Crash Michael Moore Anne Hathaway James Franco
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