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The 9 Most Chaotic Oscars Acting-Category Upsets (of the Last 25 Years)

Photo-Illustration: Vulture; Photos: Fox Searchlight Pictures, Sony Pictures Classics, Warner Bros Pictures

Is there a more thrilling awards-season possibility than the Oscars upset? After weeks and months of insiders’ predictions and whispers that leave us feeling smug about who will triumph on Oscars Night, the last-minute upset is a necessary reminder that, at the end of the day, we don’t know a damn thing. Sometimes a steamroller of a performance gets nipped at the last second. Sometimes a Hollywood legend loses out to an upstart whose acceptance speech is 70 percent stunned silence. Sometimes the favorite to win loses out to, well, The Favourite.

These upsets shock, disappoint, and exhilarate us, sometimes all at once. And the most memorable ones are always in the acting categories, if for no other reason than it means we can watch all five nominees’ faces react to the news live. Over the last 25 years, nine upsets in the Oscar acting categories have stood out as particularly stunning. Here they are, ranked in order of how unexpected each win was heading into the big day.

9. Best Supporting Actress, 80th Academy Awards

Date: February 24, 2008
Winner: Tilda Swinton, Michael Clayton
Presumed Favorites: Ruby Dee, American Gangster and Cate Blanchett, I’m Not There

The Best Supporting Actress race for the films of 2007 was one of the great wide-open races in recent memory. Nearly every nominated actress seemed to have a claim to the win: Amy Ryan had swept the major critics’ prizes for her turn as the drug-addicted, vulgar mother of a missing daughter in Gone Baby Gone. Cate Blanchett had won the Golden Globe that year (though that ceremony had been truncated into a press conference due to the WGA strike) for her flashy role as Bob Dylan in director Todd Haynes’s I’m Not There. Ruby Dee, in a small but impactful role as Denzel Washington’s mother in American Gangster, had won the SAG and seemed to have the strongest forward momentum going into Oscars Night. And 13-year-old Saoirse Ronan, enjoying her breakthrough nomination as a meddlesome little girl in Atonement, hadn’t won any major precursors but was potentially next in a long line of child actresses like Tatum O’Neal and Anna Paquin to win the Oscar.

Few were betting on Tilda Swinton to win for her performance as the nerve-jangled corporate attorney in Michael Clayton, not even after she won the BAFTA. For one thing, neither Dee nor Ryan were nominated in that BAFTA category, and Brits winning the BAFTA never seems all that surprising. For another, Swinton was still seen largely as a Hollywood outsider, having come up through the films of Derek Jarman and Sally Potter. Lucky for us, she won in a shocker and then proceeded to deliver an acceptance speech that referenced co-star George Clooney’s rubber bat-nipples, so in a way, we all won.

8. Best Supporting Actor, 71st Academy Awards

Date: March 21, 1999
Winner: James Coburn, Affliction
Presumed Favorite: Ed Harris, The Truman Show

Paul Schrader’s Affliction had a hard enough time fighting for Nick Nolte’s performance in the Best Actor race in 1998. The subject matter (a small-town sheriff dealing with an unsolved crime and dark family secrets) was grim, and the studio (Lionsgate) was barely a year old and had another, more Oscar-friendly contender in its stable in Gods and Monsters. Coburn was a Hollywood veteran, yes, but known for playing heavies in action movies and Westerns, and he was barely a presence in that year’s awards conversation until a surprise SAG nomination. He wasn’t considered a serious contender, certainly not opposite performers like The Truman Show’s Ed Harris (who’d won the Golden Globe) and A Civil Action’s Robert Duvall (who’d won the SAG). That spreading of the wealth across the season — Geoffrey Rush, for Shakespeare in Love, had won the BAFTA — probably should have indicated that the Oscar was up for grabs, but there was a prevailing sense that it was Harris’s time, as he had nearly won for Apollo 13 just a few years earlier. Instead, it was Coburn, who thanked Schrader and Nolte and then parlayed his success into voicing the role of the boss in Monsters, Inc. a few years later.

7. Best Supporting Actor, 88th Academy Awards

Date: February 28, 2016
Winner: Mark Rylance, Bridge of Spies
Presumed Favorite: Sylvester Stallone, Creed

The narrative of a potential Sylvester Stallone Oscar win for Creed felt too big to fail. Nearly 40 years after Rocky won Best Picture, Stallone was basking in a career comeback epitomized by his lifetime-achievement role in Creed, handing the franchise that had turned him into a global movie star over to Michael B. Jordan. Handing a Supporting Actor Oscar to the old, broken-down boxer was a coda fit for a movie itself. But there were warning signs along the road beyond just the low grumblings about Stallone’s popularity (or lack thereof) in Hollywood circles after decades of feuds with other action stars (Arnold Schwarzenegger, Dolph Lundgren) and dumping at least one long-term girlfriend via FedEx.

The fact that Stallone was Creed’s only Oscar nomination ought to have been a red flag that the Academy wasn’t as into the movie as some pundits thought. Then there was his SAG Awards loss to Idris Elba for Beasts of No Nation, largely brushed aside at the time (unwisely, it turned out) because Elba wasn’t on the Oscars ballot. And sure enough, on the night of the ceremony, stage veteran Mark Rylance emerged as the surprise winner for his performance as an accused Russian spy in Bridge of Spies. Rylance didn’t even recite a poem, as he does whenever he wins a Tony Award. Instead, he gave a low-key, almost nonplussed speech that must have had the telecast producers tearing their hair out at the big TV moment that was lost.

6. Best Actor, 75th Academy Awards

Date: March 23, 2003
Winner: Adrien Brody, The Pianist
Presumed Favorites: Daniel Day-Lewis, Gangs of New York and Jack Nicholson, About Schmidt

The Best Actor race for the films of 2002 was as neck-and-neck an affair as the Oscars had seen in a long while. Daniel Day-Lewis was only a onetime Oscar winner by this point in his career, but he was representing Martin Scorsese’s epic Gangs of New York with the kind of transformative, deeply committed performance that would thereafter become his trademark. Nicholson, meanwhile, was already a three-time winner, and Oscar voters had made it clear they couldn’t resist him. What’s more, his performance as a Nebraska insurance adjuster coming to terms with his dissatisfying life was hailed as a triumphant departure from the devilishly charming Jack persona that had helped win him his previous Oscars. Voters were split between them all season. Nicholson was selected by the Los Angeles Film Critics; Day-Lewis was the favorite of the New York Film Critics. Day-Lewis took the SAG and the BAFTA. Nicholson triumphed at the Golden Globes and with the prestigious AARP Movies for Grownups Awards. The two men tied at the Critics Choice Awards. Oscar prognosticators advised us to flip a coin to guess the winner.

But that’s the funny thing about awards math. When two front-runners in a five-person race end up splitting votes fairly evenly, the threshold for a third-place contestant to catch up falls a lot lower. And so there was Adrien Brody, an up-and-coming actor enjoying his first-ever nomination for playing real-life composer and Holocaust survivor Władysław Szpilman in The Pianist. As the only Best Actor nominee that year who wasn’t already an Oscar winner (also nominated were Nicolas Cage for Adaptation and Michael Caine for The Quiet American), Brody was initially seen as the category’s underdog, which had its advantages. With The Pianist surging late in the Oscars race — it would end up winning for its screenplay and, controversially, for its director, Roman Polanski — it was Brody’s unexpected triumph over Nicholson and Day-Lewis that now lives on in Oscars lore after he took to the stage and planted an unannounced kiss on presenter Halle Berry.

5. Best Supporting Actress, 69th Academy Awards

Date: March 24, 1997
Winner: Juliette Binoche, The English Patient
Presumed Favorite: Lauren Bacall, The Mirror Has Two Faces

In the long history of “overdue” Oscar narratives, Lauren Bacall’s was one of the strongest. Then 72 years old, Bacall was a Hollywood legend as much for her performances in films like To Have and Have Not and The Big Sleep as for her marriage to her co-star in those films, Humphrey Bogart. But industry respect had eluded her in those years, which yielded her not even a single nomination. And now, having earned raves for her performance as Barbra Streisand’s mother in Streisand’s The Mirror Has Two Faces, she was considered a lock to finally win. But the Oscars have always had a funny relationship with Streisand the director, finding ways to snub her and her films, including Yentl and The Prince of Tides, in one way or another.

Maybe that’s why, when the envelope was opened, the winner turned out to be not Bacall but Juliette Binoche. Her role as a World War II combat nurse tending to a burned Ralph Fiennes in The English Patient had earned raves, though beyond that, she was mostly unknown to those not attuned to French-language cinema and art-house fare like The Unbearable Lightness of Being and Damage. When she was announced the winner, fellow nominees Joan Allen and Barbara Hershey went wide-eyed, and they weren’t the only ones. Seeming genuinely stunned, Binoche took the stage in an iconic chocolate-brown dress with a dramatic high collar and said what everybody was thinking: “I thought Lauren was going to get it.”

4. Best Supporting Actress, 73rd Academy Awards

Date: March 25, 2001
Winner: Marcia Gay Harden, Pollock
Presumed Favorite: Kate Hudson, Almost Famous

The question going into the Oscars in 2001 was this: Had anybody actually seen Pollock? (Or rather, it might have been had anybody been talking about Pollock at all.) Director and star Ed Harris’s passion project about the painter Jackson Pollock had barely played on more than 200 screens by the time the Oscars rolled around, and surprise nods for Harris in Best Actor and Marcia Gay Harden — who’d played Lee Krasner, Pollock’s long-suffering wife — in Best Supporting Actress seemed like reward enough. Harden had actually won the New York Film Critics Circle prize toward the beginning of that season, though that was long forgotten by the time Kate Hudson emerged as the front-runner.

Hudson was not only the luminous point of adoration for Cameron Crowe’s Almost Famous, but she was also a legacy in the very category she was nominated in — her mom, Goldie Hawn, won Best Supporting Actress for 1969’s Cactus Flower. Hudson took the Golden Globe that January, and it felt like we were in for another second-generation coronation as we’d seen in recent years with Mira Sorvino and Angelina Jolie. Even when Hudson dropped the SAG Award to Judi Dench for Chocolat, it didn’t seem to dent her Oscar chances, since Dench had already won the Oscar only two years prior. But when Nicolas Cage read the winner’s name aloud, it was one of the all-time Oscar shocks, punctuated by Harden’s appreciative (if bafflingly low-key) “what a thrill” response. In her speech, Harden thanked Academy members for watching their screener tapes, a rather direct acknowledgment of the fact that Pollock’s Oscars success came not from its art-house screenings but from Sony Pictures Classics making sure voters got a copy to watch at home.

3. Best Actress, 91st Academy Awards

Date: February 24, 2019
Winner: Olivia Colman, The Favourite
Presumed Favorite: Glenn Close, The Wife

There is an irresistible pull to Olivia Colman’s Best Actress win over presumed front-runner Glenn Close; it’s one you play back again and again, not unlike the Zapruder film, to watch everybody’s reaction. The entire Oscars season had felt like one long coronation for the then-seven-times-nominated but zero-times-a-winner Close, who hides what must have been her crushing disappointment remarkably well. She had been nominated for her performance in The Wife, a movie that may well have only been made with Close’s eventual Oscar win in mind. It had premiered at the Toronto Film Festival the year before and thus had been accumulating Oscar buzz for over 15 months. The problem? Nobody seemed to really love the movie, even those who enthused about Close’s performance in it. We’ll never know for sure if this is why she lost. (As with all Oscar theories, you can easily poke holes in this rationale, considering Meryl Streep had recently won her third Oscar for the largely reviled The Iron Lady.)

Meanwhile, Olivia Colman, while far from holding the revered status in Hollywood that Close enjoyed, represented a Best Picture–nominated film with ten nods overall. A lot of the awards chatter that year was spent debating whether the three Favourite actresses (Colman, Emma Stone, and Rachel Weisz) ought to be submitted along lead or supporting lines. That may have obscured actual consideration among pundits of Colman’s committed and often deeply, darkly funny performance as Queen Anne. Her triumph over Close feels resistant to any narrative beyond “the voters just must’ve liked her better” — dissatisfying for us Oscars fans but which surely pleases Colman just fine.

2. Best Supporting Actor, 79th Academy Awards

Date: February 25, 2007
Winner: Alan Arkin, Little Miss Sunshine
Presumed Favorite: Eddie Murphy, Dreamgirls

The narrative of this Oscars upset has been swallowed up by one of Hollywood’s youngest urban legends, namely the so-called Norbit Effect. With Eddie Murphy enjoying his long-awaited first Oscar nomination for playing the high-energy James “Thunder” Early in Dreamgirls, he had all the momentum to ride to a widely predicted win, especially after sweeping the Golden Globes, SAG, and the Critics Choice Awards. Then, in early February, came the release of Murphy’s latest film, Norbit. Featuring Murphy playing the dual roles of meek Norbit and — in a fat suit — Norbit’s monstrous wife Rasputia, Norbit was a glaring contradiction of Murphy’s Oscars-season narrative, which cast him as a gifted actor finally emerging from a decade of flops and taking his career seriously again. As the legend goes, Norbit so turned off Oscar voters that they ran to the next-best choice.

Whether or not the Norbit Effect is real or apocryphal is impossible to prove. Dreamgirls had already been left off the Best Picture lineup, turning out to be less of the Oscars front-runner pundits had presumed. But it was still a massive bombshell when the Oscar went to Alan Arkin for his role as the lovable, irascible, heroin-taking grandpa in Little Miss Sunshine. Arkin’s long and accomplished career was as worthy of Oscar recognition as anyone’s, but most saw Murphy as a robbery victim — including Murphy himself, who left the Oscars ceremony soon after he lost.

1. Best Actor, 93rd Academy Awards

Date: April 25, 2021
Winner: Anthony Hopkins, The Father
Presumed Favorite: Chadwick Boseman, Ma Rainey’s Black Bottom

This would have been an upset on the merits alone. Anthony Hopkins was enjoying a late surge in the Oscars race, as his film, The Father, was one of the very last Oscar movies to be seen (it played in theaters despite the pandemic and wasn’t readily available on streaming platforms, as many of the nominees were that year). Still, it was widely accepted that a posthumous Oscar win for Chadwick Boseman’s shattering performance in Ma Rainey’s Black Bottom was both the correct and most likely outcome for a career cut tragically short. That narrative felt so solid that Oscars producer Steven Soderbergh moved the Best Actor presentation to come after Best Picture in order to end the evening on an emotional high. It was a break in protocol that would live in infamy as Hopkins — who wasn’t even there to accept the award — won his second career Oscar.

As is the through-line in a lot of these upsets, we probably should have seen this possibility coming, at least after Hopkins triumphed at the BAFTAs. The Father was a Best Picture nominee, while Ma Rainey was not. Hopkins was hugely popular with the Academy in the early 1990s and was now enjoying two more nominations in as many years. And Viola Davis had been accumulating Best Actress momentum for Ma Rainey, possibly weakening some voters’ desires to give the film both top acting awards. Whatever the reason, Boseman’s posthumous defeat left that Oscars Night feeling frustratingly incomplete. If nothing else, at least, it should serve as a cautionary tale to Oscars producers to never again budge on giving out Best Picture last.

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The 9 Most Chaotic Oscars Acting-Category Upsets