The agony and ecstasy of Oscar night is nothing new. Everyone wants to see their favorites win, and no one enjoys seeing a movie they dislike canonized as Best Picture. This happens every year, of course, but some winners — and losers — have been more shocking than others. Here are eight of the latter, and the stories behind their surprising losses.
"Citizen Kane" (1941)
Despite being the consensus choice for Greatest Movie of All Time, Orson Welles’ masterwork wasn’t even named the greatest movie of 1941. That honor went to How Green Was My Valley, which doesn’t often get discussed outside the context of its Oscar glory. That’s unfortunate, as it’s actually a wonderful movie and not at all the undeserving usurper it’s sometimes portrayed as. Citizen Kane’s loss is more surprising in hindsight than it may have been at the time: Welles based his eponymous character on newspaper magnate William Randolph Hearst, who used his massive influence to limit the film’s theatrical success.
Welles himself received an honorary statue in 1971 but never won a competitive Oscar — nor did he receive another nomination after Citizen Kane. That too is unfortunate, as his 1942 follow-up, The Magnificent Ambersons, is even better.
"High Noon" (1952)
It’s a dynamic we’ve since seen several times: The lighthearted crowd-pleaser beats out the more conventionally “serious” picture. In this case it was The Greatest Show on Earth taking home the big one over Stanley Kramer’s classic Western, whose reputation has brightened as the Cecil B. DeMille big-tent production’s has dimmed. The Greatest Show on Earth frequently appears on lists of the worst Best Picture winners of all time, a dubious distinction it shares with the likes of Crash and Around the World in 80 Days.
"Dr. Zhivago" (1965)
Not unlike Citizen Kane, David Lean's epic adaptation of Boris Pasternak's novel is considered one of the greatest movies ever made. The Academy didn’t seem to agree, though the competition was admittedly stiff: The Sound of Music claimed the top prize that year. Even so, the film was hardly a failure: Dr. Zhivago won five of the 10 Academy Awards for which it was nominated (three technical prizes along with Best Adapted Screenplay and Best Original Score), is among the 10 highest-grossing films of all time when adjusted for inflation, and has seen its legacy grow in the half-century since its release. The same can be said of Lean, who received seven Best Director nominations and won twice, for Lawrence of Arabia and The Bridge on the River Kwai.
"Network" (1976)
1976 was such a stacked year that it’s genuinely difficult to pick only one surprise loser; true to the scrappy underdog nature of its title character, Rocky triumphed over Taxi Driver and All the President’s Men. Network may have been the biggest shock on Oscar night, however, for the extent to which it captured the late '70s zeitgeist. “I'm as mad as hell, and I'm not going to take this anymore!” is among the most-quoted lines in movie history, and each passing year has shown just how frighteningly prescient this story of a TV network's attempt to rebound from lagging ratings truly was.
"Goodfellas" (1990)
It’s easy to forget now, but Martin Scorsese used to exemplify the phrase “always a bridesmaid, never a bride.” Taxi Driver, Raging Bull, Goodfellas, Gangs of New York, and The Aviator were all nominated for Best Picture before The Departed finally won in 2006, which was also the year Scorsese finally took home an individual trophy (for Best Director) after seven unsuccessful nominations. None of those losses stung quite like Goodfellas, which came up short against Dances With Wolves. Kevin Costner’s sweeping Western had such a troubled production that some jokingly referred to it as Kevin's Gate, a riff on the disastrous (and, in hindsight, unfairly maligned) Heaven's Gate, but the film was instantly successful with critics and audiences alike. Its Oscar glory wasn’t a huge shock at the time, but looking back on Goodfellas as anything but a Best Picture winner remains jarring nevertheless.
"Saving Private Ryan" (1998)
Despite being only the second-best World War II movie of 1998 (hello, The Thin Red Line), Steven Spielberg’s blockbuster was easily the year’s biggest film. It earned $482 million at the global box office, inspired countless parodies, and cemented Spielberg's status as one of our era's defining filmmakers. If you're curious how it lost Best Picture to the comparatively breezy Shakespeare in Love after all that, the answer is fairly simple: Oscar campaigns are ruthless, especially those masterminded by Harvey Weinstein before his well-deserved fall from grace.
Shakespeare in Love's win is considered such an upset, in fact, that the movie's Wikipedia page has a section named “Best Picture and Best Actress Oscar controversy,” and a poll of Oscar voters taken last year indicated that Saving Private Ryan would have won if there had been a do-over.
"Brokeback Mountain" (2005)
In that same poll, Academy members said they would now name Brokeback Mountain 2005’s Best Picture over Crash — something the vast majority of pundits and industry insiders expected at the time. Not only was Ang Lee's gay romantic drama a critical and financial success, but it also won top prizes at the Venice Film Festival, Golden Globes, British Academy Film Awards, Producers Guild of America Awards, and Directors Guild of America Awards — all of which are Oscar precursors that frequently align with the eventual Best Picture winner. Crash’s surprise victory was instantly criticized, with many attributing it to homophobia. Those accusations have not lessened with time, and the film has often been called the worst Best Picture winner of all time.
"La La Land" (2016)
There’s surprising, and then there’s the moment that La La Land was mistakenly announced as having won Best Picture after Warren Beatty and Faye Dunaway were handed the wrong envelope. The error didn't come to light until the musical romance's producers were well into their acceptance speeches, with producer Fred Berger ending his speech by saying, “We lost, by the way.” Moonlight — an LGBTQ+ drama directed by a Black man and made for just $1.5 million, a shoestring budget compared to the amounts allocated for most awards contenders — would have been an unexpected winner under any circumstances, but being part of the most shocking moment in Oscar history elevated its victory to an unprecedented level. To their credit, the makers of La La Land handled their not-quite-victory with utmost grace; after realizing the error, producer Jason Horowitz said he was “really proud to hand this to my friends from Moonlight.”
Despite not being the kind of movie that usually wins Best Picture, Moonlight is the opposite of undeserving. It was far and away the most well-reviewed film of 2016, won a total of 161 awards, and has since been named the best movie of the decade by several groups.
