With Los Angeles still reeling in the aftermath of devastating wildfires and the Oscar race in complete disarray following a controversy centered on Emilia Pérez’s Karla Sofía Gascón, it’s a wonder that the 2025 Academy Awards are still going ahead. The ceremony will have to reconcile entertaining an ever-declining TV audience with being sensitive to the challenges currently faced by the event’s host city, while also managing the awkwardness of its top nominee now being marred by scandal. Surely we’ll all be watching through our fingers.
Still, even all of that might not actually make it the weirdest Academy Awards ceremony of all time. Below, we take a look back at eight unforgettable Oscar nights from the last 25 years.
2002: A post-9/11 love letter to New York
Six months after the September 11 attacks, many suggested that the Oscars ceremony should be postponed or canceled. But the Academy doubled down, with its then president, Frank Pierson, writing 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, though with heightened security, and none other than 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.” Later on in the evening came a moving tribute to New York and a plea to filmmakers to keep working there, followed by a sweeping montage compiled by local hero Nora Ephron.
2003: The Iraq war divides the room
Just a year later, the mood had shifted from a kind of somber solidarity to something more divisive. Bizarrely, the 75th Academy Awards took place only three days after the surprise US invasion of Iraq. Hours after that news broke, several Oscar presenters, including Cate Blanchett and Jim Carrey, stepped down from their roles, and the show’s broadcaster, ABC, asked that it be postponed. Still, the Academy, citing logistical issues, refused. The usual red-carpet hoopla was significantly curtailed, though, and news updates were delivered during commercial breaks. (In truth, most viewers were watching live coverage of the war instead, with the Oscars earning its lowest viewership up until that point.)
Then came the moment that finally bled through this barrier between the undeniably tone-deaf Hollywood fantasia and horrifying rolling news: Michael Moore taking to the podium to accept his best-documentary-feature Oscar for Bowling for Columbine and condemning the 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!” Cue both boos and wild 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 face said it all, once he opened the envelope—for a second he looked concerned, and then announced the victor, raised his eyebrows, and mouthed the word “whoa” to someone backstage. The win is still remembered as one of the most baffling in Oscars history.
2011: The weirdest Oscars hosting duo of all time
In a bid to capture a younger demographic, Anne Hathaway and James Franco were hired to host the 83rd Academy Awards and it was, well, a bit of a disaster. She was wide-eyed and earnest, he was stiff and low-energy, and it was incredibly painful to watch, from the cringe-worthy opening monologue to the fumbled mid-ceremony announcements. 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 an agonizing, awkward, and then jubilant eight minutes. First of all, Bonnie and Clyde’s Faye Dunaway and Warren Beatty came on stage to present best picture; he looked at the winner’s card with confusion, double-checked the envelope, and looked around for help; she giggled at him like he was doing a bit and then, upon being handed the card herself, announced, “La La Land.” It made sense—Damien Chazelle’s dreamy-eyed musical had already scooped six prizes. The cast and crew took the stage, emotional speeches were given, and all the while, Beatty remained in view, looking troubled.
As producer Marc Platt got his moment at the microphone, fellow winners Jordan Horowitz and Fred Berger shared a look, after which officials with headsets came into view to check the envelope. Berger shouted out his family and colleagues and then said, “We lost, by the way.” Then, Horowitz said the immortal words: “There’s a mistake. Moonlight, you guys won best picture,” before holding up the correct card for everyone to read.
People screamed, and Moonlight’s director, Barry Jenkins, made his way up onto the stage, his jaw on the floor. Naomie Harris looked shocked. Shirley MacLaine had her mouth hanging open. Busy Philipps was laughing her head off. Matt Damon started whistling. Taraji P. Henson started filming the incident on her phone. Samuel L. Jackson wiped away a tear. Then, the Moonlight team got their moment. In a word: incredible.
2019: Green Book triumphs over Roma
In a moment that felt eerily similar to Crash’s victory more than a decade prior, the much-maligned Green Book was named best picture over the presumed favorite, Roma, at the 91st Academy Awards—though Julia Roberts did at least learn a valuable lesson from Jack Nicholson’s reaction, and smiled sweetly as she made the announcement. While the film’s cast and crew were triumphant, everyone else looked a little confused.
2021: The COVID Oscars
Didn’t have Glenn Close getting down to “Da Butt” on your Oscars bingo card? Er, me neither. But the 93rd Academy Awards, which took place while the world was still in the grips of the pandemic, gave us plenty of things we didn’t expect: a new, more socially distanced venue in LA’s Union Station with cabaret-style seating; a very strange, “cinematic” opening; and perhaps the most abrupt ending ever, in which the best-actor prize—widely expected to go to Chadwick Boseman, posthumously, and so moved to the end of the night—went instead to an absent Anthony Hopkins. Yikes.
2022: The Slap
An ill-judged G.I. Jane joke from presenter Chris Rock. A smattering of laughter. Then a long walk up to the stage for best-actor frontrunner Will Smith, who smacked the comedian in the face and, famously, told him to keep his wife’s name out of his mouth. More laughter from those who assumed this was a planned sketch. Then, more yelling and the slowly dawning realization that this was not, in fact, planned. After that, a gruelling wait during which everyone in the world tried to work out what the hell was going on, and then Smith collected his Oscar and gave a tearful speech about how “love will make you do crazy things.” As Rock said on stage in the immediate aftermath of the incident, “That was the greatest night in the history of television.” Whatever happens this year, it surely can’t be as bad as that?
