‘Always Getting It Wrong’: The 10 Worst Oscar Wins of All Time

With the 2023 Oscars ceremony just wrapped, Deeper Into Movies felt it was time to enlist the help of their pal, writer and Oscars aficionado Michael Schulman, to create a top ten list of the wrongest Oscar wins of all time. Schulman’s latest book, Oscar Wars: A History of Hollywood in Gold, Sweat, and Tears, looks back on nearly a century of scandal, conflict, and cultural fissures kicked up by the Academy Awards. 

“I hate to shock anyone, but the Academy Awards are not a pure barometer of cinematic worth. All sorts of factors go into who’s nominated and who wins: campaign cash, personal popularity, politics, racism, status in the industry. If you look to the Oscars for a definitive film canon, you’ll be perpetually disappointed or enraged. That’s why I begin my book Oscar Wars with the line “The Oscars, it should be said at the start, are always getting it wrong.”

But that doesn’t mean that the Oscars are worthless: They’re a reflection of how the industry sees itself, and they have ramifications on what movies get made and promoted. Often, they act as a prism to help us understand where Hollywood and American popular culture are headed. Plus, complaining about what the Academy got wrong is part of the fun. 

To put it simply, the list of major talents who never received an Oscar is staggering. Neither Stanley Kubrick or Alfred Hitchcock ever won Best Director, and stars like Rita Hayworth, Barbara Stanwyck, Cary Grant, and Marilyn Monroe never won a competitive acting Oscar. Here are ten notable wins that have left cinephiles scratching their heads down the decades.” - Michael Schulman

I actually think Davis is fine in Dangerous, where she plays a tempestuous actress who worries that she’s a bad-luck charm. But you know who didn’t think she should win? Bette Davis. She’d been snubbed the year before, when she wasn't nominated for Of Human Bondage, and the outcry led the Academy to open up the final voting in 1935 to write-in campaigns. Though this didn’t make much difference, with Davis still losing to Claudette Colbert for It Happened One Night, the next year Davis had a second chance with Dangerous. 

Davis thought the script was “maudlin and mawkish” and in her memoir The Lonely Life, she even said this: “I was up against Katharine Hepburn’s brilliant Alice Adams, by far the best performance of the year.” When Davis then won, she knew in her bones that it was a consolation prize for Of Human Bondage. “It was true that even if the honour had been earned, it had been earned last year,” she reflected. Don’t feel too bad for Hepburn, though: she’s won a total of four Oscars, still the record for any actor.

An all-time Oscar shonda! In 1942, Citizen Kane got nine nominations, including Best Picture, Best Director, Best Actor, and Best Original Screenplay for its auteur-star, Orson Welles (though shared, uneasily, with Herman Mankiewicz). It was clear that Citizen Kane was a masterpiece, and, leading up to Oscar night, Variety predicted that the film was “doped to win a flock of Oscars”.

But it didn’t come to pass. Kane lost every single prize except one, for its screenplay. John Ford’s How Green Was My Valley, a wistful tale of life in a Welsh mining town, won Best Picture. The speculation over what had happened began immediately: Had the Academy voters rejected Welles because he was an outsider? A newcomer? Had the scandal over Kane’s thinly veiled depiction of press magnate William Randolph Hearst exhausted the industry? Was Welles’s complete artistic control a threat to the assembly-line studio system?

Or was there simply a reverence for Ford, whose classic The Grapes of Wrath had lost Best Picture the year before? As Pauline Kael later wrote, “The members of the Academy destroyed Orson Welles that night.”

The first Academy Awards to be televised showed the world just how glamorous – and how wrong, wrong, wrong – the Oscars could be. Cecil B. DeMille’s The Greatest Show on Earth is remembered as one of the worst Best Picture winners of all time: a gaudy circus spectacular long on trapeze stunts and short on coherence. But DeMille was in his veteran phase, and the movie was the kind of Technicolor spectacle that Hollywood embraced amid the threat of television. 

Industry politics came into play too: Fred Zinnemann’s tense, ingenious Western High Noon was not only a metaphor for Hollywood’s cowardice during the blacklist era but was written by Carl Foreman, who was blacklisted himself. One Paramount executive on the Academy board told a CIA contact he’d been working behind the scenes to prevent a High Noon win. 

Years later, High Noon producer Stanley Kramer reflected, “I still believe High Noon was the best picture of 1952. But the political climate of the nation and the right-wing campaigns against High Noon had enough effect to relegate it to an also-ran status.” The cherry on top of all that wrongness: Singin’ in the Rain wasn’t even nominated for Best Picture.

The soon-to-be Princess Grace stripped off her glamour for The Country Girl, becoming the drab, beleaguered wife of an alcoholic actor (Bing Crosby). This has been a reliable route to the Best Actress prize through the ages (think of Charlize Theron in Monster or Halle Berry in Monster’s Ball). But Kelly was up against one of the most titanic performers of the twentieth century, in arguably her greatest role: Judy Garland in A Star Is Born. 

The role required Garland to sing, dance, self-destruct, and practically bleed on screen. Her performances of songs like “The Man That Got Away” are indelible, too. Garland gave birth prematurely two days before the ceremony, and NBC set up cameramen outside her hospital room in case she won. When she lost, the cameramen packed up their equipment and Garland’s husband Sid Luft told her: “Baby, fuck the Academy Awards – you’ve got yours in the incubator.”

With apologies to the baby, Joey Luft, I’d have rather she got her award. Also in the category was Dorothy Dandridge for Carmen Jones, the first Black woman nominated for Best Actress. Had she won – nearly 50 years before Berry finally broke the colour barrier – the Academy’s woeful history of honouring women of colour would have been very different.

Quick, tell me what Stanley Kubrick won an Oscar for. If you guessed Best Special Visual Effects for 2001: A Space Odyssey, you are unfortunately correct. Astoundingly, he never won the Best Director prize. He was nominated for Dr. Strangelove in 1965, but lost to George Cukor for My Fair Lady. In 1969, when he entered 2001 into the awards race, he lost out to Carol Reed for Oliver! When it was The Clockwork Orange’s turn in 1973, he lost to William Friedkin for The French Connection.

Three years later, Barry Lyndon was beaten by Miloš Forman’s sweep for One Flew Over the Cuckoo’s Nest. Kubrick’s last Oscar nomination – Best Adapted Screenplay for Full Metal Jacket – was in 1989. He lost to The Last Emperor. As for Spartacus, The Shining, and Eyes Wide Shut… the man wasn’t even nominated.

One director who had it even worse than Kubrick was Martin Scorsese, who managed not to get nominated for Mean Streets, Alice Doesn’t Live Here Anymore or Taxi Driver. His first nomination finally came in 1981 for Raging Bull, adapted from the boxer Jake LaMotta’s autobiography. But by then, the rambunctious New Hollywood of the 70s was fading and contemporary movies were beginning to reflect Ronald Reagan’s America of the 80s. That shift is palpable in Robert Redford’s directorial debut, Ordinary People, a domestic drama about a WASPy suburban family. 

In a bizarre turn of events, the scheduled Oscars date happened to coincide with John Hinckley’s Jr.’s attempted assassination of President Reagan and the ceremony was consequently postponed (even more bizarre, Hinckley Jr. had been trying to impress Jodie Foster after obsessing over her performance in Taxi Driver). 

When the Oscars did happen, De Niro won for his famously immersive performance as LaMotta, but Ordinary People won for Best Director and Best Picture. A decade later, Scorsese was up again for Goodfellas and again lost both prizes to a sentimental favourite directed by a movie star: Kevin Costner’s Dances with Wolves. Scorsese finally won in 2007 for The Departed (which is nobody’s favourite Scorsese film).

The Best Original Song category is always a doozy, but my personal gripe is with ‘You Must Love Me’ the song that Andrew Lloyd Webber and Tim Rice dropped into the movie version of Evita (presumably to give Madonna a new song and themselves a chance to win an Oscar). 

The score of Evita certainly doesn’t need another showstopper: After ‘Don’t Cry for Me, Argentina’, ‘You Must Love Me’ is little more than a generic snoozy ballad. Among the songs this lacklustre number beat was the title bop of That Thing You Do!, by the late, great Adam Schlesinger. It’s an infectious tune that plays a central role in the story, a convincing pastiche of 60s bubblegum pop that stands up on its own merits.

Another loser was “Because You Loved Me” by Diane Warren, which Celine Dion sang for Up Close and Personal. While Dion would of course be back the next year with an Oscar-winning ballad “My Heart Will Go On”, Warren is currently on her 14th nomination with zero wins. 

You knew we’d get here. Perhaps the most infamous Best Picture winner is Paul Haggis’s Crash. Crash tells interweaving stories of racial tensions in Los Angeles, a topic that was likely of special interest to Academy members who were able to pat themselves on the back for embracing its bleeding-heart values. That self-satisfied liberalism didn’t extend to Ang Lee’s Brokeback Mountain, a far superior movie that was groundbreaking in its telling of a gay love story between two cowboys (played by Heath Ledger and Jake Gyllenhaal). 

In an era of heated debate over gay marriage, you can’t count out homophobia as a major hurdle for Brokeback’s Oscar chances. Lee won Best Director, deservedly, but Crash took the top prize. Another disappointment that night: Ledger lost the Best Actor race to Philip Seymour Hoffman for Capote. Hoffman was, of course, one of the greatest actors of the 21st century. But his affected portrayal of Truman Capote – complete with the Droopy Dog voice – is the kind of performance that undeservedly appeals to Academy members over a quiet, soulful, based-on-no-one performance like Ledger’s. Both actors died far too young, and Ledger won a posthumous Oscar in 2009, for The Dark Knight.

Richard Linklater began filming Boyhood in 2002 and finished it in 2013, capturing the real-life coming-of-age of the child actor Ellar Coltrane. This startling feat produced a kind of realism that had never been achieved on film, as we watch Coltrane’s character age from a watchful six-year-old to a deep-voiced teenager leaving for college. This was more than a gimmick: It was a new way of capturing time. 

However, Alejandro González Iñárritu’s Birdman or (The Unexpected Virtue of Ignorance) also had a technical twist: The movie, thanks to seamless editing, appeared to be filmed in one continuous shot. It also represented a comeback for Michael Keaton, in the self-referential role of a movie star famous for playing a superhero attempting a prestige comeback.

It’s a film with far less heart and soul than Boyhood, but it charmed the Academy. On Oscar night, Boyhood won only one award, for Patricia Arquette’s stunning supporting turn as the boy’s mother. Birdman, on the other hand, won four awards, including Best Director and Best Picture. I haven’t thought about Birdman since, while Boyhood still lives in my brain.

In a repeat of the Crash year, a middlebrow movie about racial tolerance beat a better crafted, more personal, and more sophisticated opponent. The director Alfonso Cuarón dug deep into his past for Roma, which revisited his childhood in Mexico from the perspective of his Indigenous maid, played with understated depth by Yalitza Aparicio. But Cuarón’s incandescent black-and-white cinematography and gargantuan campaign from Netflix were no match for Green Book, Peter Farrelly’s civil-rights-era parable loosely based on the relationship between the Black pianist Don Shirley and his white driver (which Shirley’s relatives said the movie greatly inflated). 

Though Farrelly was left off the Best Director list – which Cuarón won – Green Book beat not only Roma, but Spike Lee’s BlacKkKlansman for Best Picture. Speaking of bad Oscar calls, Lee hadn’t been nominated for directing Do the Right Thing in 1990 either. This was the year that Driving Miss Daisy – another maudlin story a cross-racial friendship between driver and passenger – won. “I’m snake-bit,” Lee told the pressroom after Green Book won. “Every time somebody is driving somebody, I lose.”

Oscar Wars A History of Hollywood in Gold, Sweat, and Tears is out now, published by Harper Collins.