The 20 biggest Oscar upsets of all time — and where the stunning ‘Moonlight’ win ranks

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“Moonlight.”

Regardless of if you love watching the Oscars or love to hate-watch the awards, the highlight is always when there’s an upset winner — and that happened in spectacular fashion at Sunday night’s Oscars.

With months of predictions about why a person or film is going to win, there’s nothing like watching the genuine surprise and spontaneous, authentic reaction when someone seems to steal away Hollywood’s biggest prize. That can range from Roberto Benigni standing on his seat after winning best actor in 1999 to Adrien Brody planting a big kiss on presenter Halle Berry when he won the award in 2003.

And now we can add to that list the shocking best-picture upset by “Moonlight” over “La La Land,” and the confusion amid the announcement of the award, at the 2017 Oscars.

Here are the 20 biggest upsets in Oscar history, and where “Moonlight” ranks:

20. Anna Paquin wins best supporting actress for “The Piano” (1994)

Rarely does the Academy award children, but at 11 years old Paquin took the award, beating out Emma Thompson (“In the Name of the Father”), Winona Ryder (“The Age of Innocence”), Rosie Perez (“Fearless”), and Holly Hunter (“The Firm”), who was also nominated in the best actress category for playing opposite Paquin in “The Piano.” She would win in that category.

19. “The King’s Speech” wins best picture (2011)

What was thought to be a film that would showcase Colin Firth’s talents to earn him an Oscar (and it did), the movie shocked the likes of nominees “The Social Network,” “The Fighter,” and “127 Hours” to win the top prize.

18. Grace Kelly beats Judy Garland for best actress (1955)

Judy Garland had an iconic career but never received an Oscar (not counting her 1940 juvenile award for best performance by a child actor). Her best chance was for “A Star Is Born” in 1955 but Grace Kelly got the best actress prize instead. A puzzling choice by the Academy voters, especially since her win went for her role in the forgettable “The Country Girl” when in the same year she starred in Hitchcock classics “Rear Window” and “Dial M for Murder.”

17. Juliette Binoche beats Lauren Bacall for best supporting actress (1997)

Another legend who was supposed to get a long-awaited Oscar was Lauren Bacall for her performance in “The Mirror Has Two Faces” but instead Juliette Binoche got best supporting actress for “The English Patient.” Bacall never got over it, and in her autobiography she admitted she really wanted the Oscar and blamed the aggressive campaigning by “Patient” distributor Harvey Weinstein.

16. Geoffrey Fletcher wins best screenwriting for “Precious” (2010)

Up against the likes of Armando Iannucci (“In the Loop”) and Jason Reitman (“Up in the Air”), Geoffrey Fletcher was an unlikely bet for his Oscar.

15. Art Carney beats Al Pacino and Jack Nicholson (1975)

Sometimes the Academy gives out an Oscar more for a person’s career than the performance and that’s what happened here. There’s really no other explanation for how Art Carney in “Harry and Tonto” won best actor over Al Pacino in “The Godfather Part II” and Jack Nicholson in “Chinatown.”

14. “The Greatest Show on Earth” beats “High Noon” for best picture (1953)

In the era when the Western was king, the classic “High Noon” shockingly lost to life under the big top with Charlton Heston and James Stewart in “The Greatest Show on Earth.”

13. Bob Fosse beats Francis Ford Coppola (1973)

Though “The Godfather” would walk away with best picture, best actor, and best screenplay it would be Bob Fosse directing “Cabaret” that would upset the movie’s evening as he took the best directing prize from Francis Ford Coppola.

12. Adrien Brody wins for “The Pianist” (2003)

Though the whole world was shocked that Adrien Brody won, it looked like Brody himself was the most surprised as he walked on the stage in a daze, even giving a big kiss to presenter Halle Berry.

11. Marisa Tomei wins for “My Cousin Vinny” (1993)

You could say Marisa Tomei has had a handful of roles in her career that she should have won an Oscar for, but it’s playing the wise-cracking Brooklyn gal Monia Lisa that got her a best supporting actress win. And it shocked the world.

10. Beatrice Straight wins for “Network” (1977)

Holding the record for winning an Oscar with the shortest screen time, Beatrice Straight’s moving performance in “Network” as a jilted wife lasted only five minutes.

9. “Rocky” wins best picture (1977)

In a year when “All the President’s Men” and “Network” led the Oscars in nominations and wins both lost the biggest prize to the ultimate underdog movie, “Rocky.”

8. Three 6 Mafia wins best original song for “Hustle & Flow” (2006)

The first ever Oscar win for a rap group was not just a landmark moment for the music genre but the then-unknown Three 6 Mafia for the song they wrote for “Hustle & Flow.”

7. Roberto Benigni wins best actor for “Life Is Beautiful” (1999)

With a field that included Edward Norton (“American History X”), Nick Nolte (“Affliction”), Ian McKellen (“Gods and Monsters”), and Tom Hanks (“Saving Private Ryan”) it was Roberto Benigni in “Life Is Beautiful” who stunned everyone with not just the win but a balancing act on chairs on the way to accepting the award.

6. “Moonlight” beats “La La Land” for best picture (2017)

For some, the best-picture win for “Moonlight” was less of a surprise than a needed dose of reality, given the #OscarsSoWhite backlash to the awards’ lack of diverse representation. However, the way the movie got the win — taking the prize despite its director, Barry Jenkins, not winning best director, and beating “La La Land,” which had a record-tying 14 nominations — was a shock. And, of course, there was the whole mix-up of first mistakenly announcing “La La Land” the winner, before correcting things amid much awkwardness, which will go down as the biggest Oscar blunder of all time.   

5. “Crash” wins best picture (2006)

Though it didn’t earn the kind of box-office dollars of its competitors, “Crash” took the best picture win, upsetting the beloved “Brokeback Mountain,” which many thought should have rightfully won. It even led to speculation of homophobia from voters.

4. “Shakespeare in Love” beats “Saving Private Ryan” for best picture (1999)

With Steven Spielberg winning best director it was assumed that best picture would go to his “Saving Private Ryan,” but the campaigning skills of Harvey Weinstein struck again, pulling off the incredible win for “Shakespeare in Love.”

3. “How Green Was My Valley” beats “Citizen Kane” for best picture (1942)

Though “Citizen Kane” has gone on to be considered one of the greatest movies ever made, at the time of its release some didn’t feel that way. Especially those who were close to William Randolph Hearst, who was the inspiration behind “Kane” character Charles Foster Kane. That likely played a factor in “How Green Was My Valley” getting the win.

2. Kevin Costner beats Martin Scorsese for best director (1991)

The “best director not to win an Oscar” narrative was building when praise for “Goodfellas” came around. Considered to be a “can’t miss,” Scorsese’s gangster classic lost to Kevin Costner’s directing of “Dances with Wolves.”

1. “Forrest Gump” beats “Pulp Fiction” and “The Shawshank Redemption” for best picture (1995)

As the years pile on the win by “Forrest Gump” becomes more of a head-scratcher. Though it was acclaimed at the time, so were “Pulp Fiction” and “The Shawshank Redemption,” which were both up for the prize that year. And while all three continue to have fans, “Pulp Fiction” stands out as a once-in-a-lifetime movie experience.

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