The Five Biggest Best Picture Upsets In Oscars History

Written By Jessica Welman on February 7, 2019 - Last Updated on May 6, 2022

When it comes to the Academy Awards, generally things go as planned.

Well, except for that whole La La Land and Moonlight snafu.

It is true though that Best Picture winners tend to be fairly expected. Even in the case of La La Land and Moonlight, many pundits predicted that La La Land peaked too soon. A wave of backlash late in awards season had many thinking it wouldn’t storm through the Oscars as it had at other ceremonies.

The dramatic envelope switch certainly helped make the upset the most memorable one in Oscar history.  That doesn’t necessarily make it the biggest upset ever though. It looked like the movie that could take down La La Land and, lo and behold it did.

Since this is the first year you can legally bet on Oscar winners — at least if you’re physically located in New Jersey — let’s take a look at five bigger Best Picture upsets that truly caught the academy off guard.

5. Driving Miss Daisy (1990)

Before this little movie that could win the award in 1990, it was a hard and fast rule that if you were not nominated for Best Director, you were not going to win Best Picture. The only times it did not happen was during the 1929 and 1932 Oscars, back when the academy was still figuring out how the Oscars would even work.

It looked as though Oliver Stone would be back in the winner’s circle just three years removed from winning for Platoon. His film Born on the Fourth of July won the Golden Globe for Best Drama, Stone won the Director’s Guild of America (DGA) award, and this “important” movie about Vietnam veterans was exactly the kind of biopic the academy goes crazy over.

It was the quiet movie based on a play about an older Southern woman and her African-American driver that took top honors. Driving Miss Daisy actually won the first-ever Producer’s Guild of America (PGA) award as well as the Golden Globe for Best Comedy, so the win was not totally out of left field.

Nonetheless, that year was definitely a David vs. Goliath story where David prevailed in the end.

4. Shakespeare in Love (1999)

Shakespeare in Love was a testament to how far Harvey Weinstein was willing to go to produce Oscar-winning movies. At the time, Weinstein was the head of the independent film studio Miramax. His relentless spending on awards campaigns was the stuff of legends. It even was the subject of a book, Peter Biskind’s Down and Dirty Pictures.

The consensus is that Weinstein outspent Dreamworks and its contender, Steven Spielberg’s Saving Private Ryan. That is how this rather fluffy and frothy romantic comedy won Best Picture. Heading into the ceremony, Saving Private Ryan had the PGA and DGA honors in its corners, not to mention the power of Spielberg.

Once Shakespeare in Love took home a huge haul at the British Academy of Film and Television Awards (BAFTA) shortly before Oscar night, the cracks in Saving Private Ryan‘s armor started to show. It didn’t help matters that another World War II movie, Terrence Malick’s The Thin Red Line was cutting into its voting block.

On Oscar night, Spielberg managed to take Best Director, but the Bard was the one who took the Best Picture Oscar home.

3. Chariots of Fire (1982)

Let’s be honest. The year 1981 was not a good year for movies. The frontrunner going into the Oscars was the lengthy epic Reds, directed by Warren Beatty. The rest of the nominees included two crowd-pleasers, Raiders of the Lost Ark and On Golden Pond, the small ensemble drama Atlantic City, and the movie about cross-country racing in Britain, Chariots of Fire.

Reds was a sweeping drama in the vein of Dr. Zhivago with the star power of Beatty, Diane Keaton and Jack Nicholson to go with it. Chariots of Fire, on the other hand, featured mostly unknowns. Additionally, Reds led the field with 12 nominations, while Chariots of Fire had just seven.

DGA honors went to Beatty, who managed to win Best Director on Oscars night. However, the academy split between Best Picture and Best Director, giving Chariots of Fire the top prize. It was definitely a surprising upset, but in a down year for Oscars all around, it is not one people tend to remember.

2. Crash (2005)

Heading into Oscar night, the only major awards Crash had won was the Writers Guild of America honor for Best Original Screenplay and the Screen Actors Guild (SAG) Award for Best Ensemble Cast.

Of course, the largest branch of the academy is the actors, so perhaps that SAG award was telling us more than we realized at the time.

By comparison, Brokeback Mountain won just about every award there was to win. It took DGA, PGA, Writers Guild for Adapted Screenplay, and the Golden Globe for Best Drama. The story of two cowboys who fall in love in a time and place where homosexuality was not tolerated had everything going for it.

How did this upset happen? The support from actors certainly helped. You could also make the argument that writer and director Paul Haggis, who was still closely tied to the Church of Scientology at the time, had the power of the church and its strong Hollywood connections behind him. Really, this seems like an instance where Crash felt a lot more socially important than Brokeback Mountian, which shifted the votes in its favor.

1. Braveheart (1996)

In what is arguably the biggest upset in Best Picture history, Mel Gibson’s tale of Scottish soldiers crashed the flight plan of Apollo 13.

The movie about the failed NASA mission looked like the Academy’s chance to honor Ron Howard with cinema’s top honors. As awards season unfolded, Apollo 13 thrived everywhere except for the Golden Globes. It won both the PGA and DGA awards, coming into the Oscars with nine nominations to Braveheart‘s 10.

Braveheart did have the most nominations, but other than a win for Best Director at the Golden Globes, it really came up empty-handed in the lead-up to Oscar night. It left Oscar night with both Best Picture and Best Director, while Howard had to wait six years to get his statuettes for A Beautiful Mind in 2002.

When it comes to forecasting, FiveThirtyEight says this win was the mathematically biggest upset in recent Oscar history.

This year though, with a relatively open field of Best Picture nominees and the major awards spread around to several different movies, there is certainly potential for the 2019 Oscars to one-up what happened in 1996.

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Jessica Welman

Jessica Welman has worked as a tournament reporter for the World Poker Tour, co-hosted a podcast for Poker Road, and served as the managing editor for A graduate of Indiana University and USC, Welman is not only a writer but also a producer. She can be found on Twitter @jesswelman.

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