1. "Saving Private Ryan" misses out on Best Picture.
Shakespeare in Love was a fun, light, and ultimately forgettable romance starring Gwyneth Paltrow. Its clever script packed in plenty of Shakespearean references, and director John Madden did an effective job of recreating Elizabethan London.
There’s nothing wrong with the film, exactly, but many movie fans believe that its 1999 Best Picture win was one of the greatest travesties in Oscar history.
Why? It was up against Saving Private Ryan, generally considered to be one of the greatest epic war movies ever made. The Stephen Spielberg–directed masterpiece featured career-defining work from Tom Hanks and Matt Damon, and its emotionally devastating opening scene is more powerful than anything in Shakespeare in Love.
The upset likely occurred due to aggressive backstage campaigning from Harvey Weinstein, the head of Miramax, on behalf of Shakespeare in Love. In any case, film fans have never really forgotten this snub.
2. Three 6 Mafia upsets Dolly Parton to win Best Original Song for "Hustle & Flow."
In 2006, rap group Three 6 Mafia performed at the 78th Academy Awards, changing a few key words of “It’s Hard Out Here” in the process. The song was featured in Hustle & Flow, a fairly well-received drama about a Memphis hustler who decides to become a rapper.
Three 6 Mafia helped define Southern rap music in the early 2000s, and their brash energy was shocking to some members of the Academy. For instance, their live performance featured the word “witches,” which very obviously replaced another well-known word from the original song.
However, the Academy wasn’t shocked enough to deny the group an Oscar. Three 6 Mafia returned to the stage to accept the Best Original Song award, beating out Dolly Parton in the process.
For her part, Parton had a huge smile on her face; after all, she knows that in the award show game, it’s hard out here.
3. "Moonlight" beats "La La Land"...eventually.
We can’t really write about Oscar upsets without addressing the awkward elephant in the room.
At the 89th Academy Awards, the big question was whether Moonlight could upset La La Land. The latter film was a musical starring Emma Stone and Ryan Gosling, and its story revolved around the wonder of Hollywood. It was a throwback piece with a massive budget and plenty of star power; in short, it was exactly the type of film that the Academy loves.
Moonlight, on the other hand, was an artful, low-budget drama with an all-black cast that dealt with difficult subjects, including homophobia and abuse.
La La Land won out...at first. You probably know what happened by now; presenter Warren Beatty was given the wrong envelope, so while the La La Land cast celebrated, they were informed that they’d lost the award.
It’s one of the most awkward moments in television history, but when the dust settled, many believed that the better film had won the award.
4. Bob Fosse beats Francis Ford Coppola for Best Director.
In 1973, Cabaret was poised to take home some Oscars. The musical was critically lauded on release, and it represented a major turning point in the career of director Bob Fosse, who’d bounced back from the failure of his previous film, Sweet Chariot.
Cabaret proved popular with the Academy, as it won awards for Best Support Actor, Best Art Direction, Best Original Song Score and Adaptation, Best Cinematography, Best Sound, and Best Film Editing. The biggest surprise, however, was Fosse’s win for Best Director.
So, where’s the controversy? Fosse won the award over Francis Ford Coppola, who’d directed the landmark masterpiece The Godfather the same year. Cabaret is still considered a fine film, but The Godfather is regularly regarded as one of the best—if not the best—films of all time.
Coppola would eventually win the Best Director award for The Godfather, Part II, which somewhat made up for this epic snub.
5. "Taxi Driver" loses Best Picture to Rocky in 1977.
We’ll resist the urge to make a joke about underdogs, but Rocky wasn’t expected to win the Best Picture honors in 1977. Martin Scorsese's brutal, disturbing Taxi Driver was clearly the better film.
Starring Robert De Niro and Jodie Foster, it’s the deeply complex tale of a man driven to insanity and vigilantism. It was a forward-thinking film that changed storytelling in cinema. In short, it deserved to win.
Of course, Rocky was also a great film, albeit with much simpler themes of willpower and redemption. Written and directed by Sylvester Stallone, it led to a sequel, then another sequel, then another sequel; eventually the power of the franchise was diminished by talking robots and appearances from professional wrestlers.
As time has passed, many critics have recognized that Rocky was punching above its weight when going toe-to-toe with the ambiguous morality and brilliant acting in Taxi Driver. For years afterwards, Scorsese failed to win Oscars for classic films like Goodfellas, prompting rumors of an intentional snub.
6. Kevin Costner wins Best Director in 1991.
Really, we could fill this list with Martin Scorsese snubs, but one of his most controversial losses came in 1991. That year, Kevin Costner directed and starred in Dances with Wolves, an epic Western film about a white man who joins an American Indian tribe.
While critically lauded at the time, Dances with Wolves hasn’t aged very well. These days, it seems like a painfully dated artifact of 1990s storytelling, although Costner’s performance was well received. In fact, because Dances with Wolves presented a positive image of American Indian tribes, Kevin Costner was given an honorary membership in the Sioux Nation. Dances with Wolves also won Best Picture, by the way.
All of that is fine, but in 1991, Martin Scorsese had created Goodfellas, an epic gangster movie which is widely considered one of the best crime films of the past century. Starring Robert De Niro, Ray Liotta, and Joe Pesci, it was another Scorsese masterpiece, and many members of the Hollywood elite were stunned when Scorsese went home without a Best Director award.
Eventually, Scorsese did take home the Best Director award for The Departed in 2007, but most critics consider The Departed to be inferior to Goodfellas.
7. Art Carney wins the Best Actor award for his role in "Harry and Tonto."
Art Carney was best known for playing Ralph Kramden in 1950s sitcom The Honeymooners, but his career continued well into the 1970s. In fact, he won the Best Actor award in 1975 for his work in Harry and Tonto, a road film about a man named Harry Coombes (played by Carney) who goes on a trip with his cat, Tonto (played by a cat).
Largely forgotten by all but the most ardent film historians, Harry and Tonto began a career resurgence for Carney, who’d finally proven that he was a capable dramatic actor.
However, the Oscar win was a major upset. The other nominees included Jack Nicholson for Chinatown and Al Pacino for The Godfather, Part II.
Critics consider those films to be timeless classics, whereas Harry and Tonto... well, one of the lead roles was played by a cat.
8. "How Green Was My Valley" beats "Citizen Kane" for Best Picture.
This is one of those Academy Award snubs that really only looks bad in hindsight. In 1941, Orson Welles’ Citizen Kane was a highly divisive film, in no small part due to William Randolph Heart’s aggressive attempts to blacklist the film.
Hearst, a newspaper baron, was convinced that Citizen Kane was a savage dramatization of his own life, and for good reason: It was.
By directing and starring in the film, Orson Welles had made himself the enemy of the most powerful media tycoon in the country, and Hearst effectively crippled Welles’ career over the next several years.
That helps to explain why How Green Was My Valley defeated Citizen Kane at the Academy Awards, taking home Best Picture, Best Director, Best Supporting Actor, and Best Cinematography accolades. Citizen Kane did win the award for Best Writing, but Welles and his co-writer, Herman J. Mankiewicz, had trouble finding mainstream work in Hollywood for years afterwards.
As time has passed, the 1941 Academy Awards look much worse. Citizen Kane revolutionized filmmaking at every level and is almost universally considered to be the most influential film ever made.