The Biggest Best Picture Upsets in Oscar History

Most years, the Oscars hold few surprises in the main category. Long before the ceremony, critics and the various guild awards have usually agreed on which movie deserves Best Picture, and on the night the Academy tends to go along with them. That is exactly why the years it didn’t are still talked about.

That agreement shows up outside Hollywood as well, because bookmakers in plenty of countries take bets on the Oscars every year and move their prices whenever a precursor award goes one way or another. Legalbet, an expert portal that reviews licensed bookmakers in Romania, compares the best online betting sites on that market, and several of them put Oscar categories right next to football and tennis. By the time the ceremony starts, the film these bookmakers rate as the likeliest Best Picture winner is almost always the one critics and guild voters have already picked.

Every now and then, though, the Academy surprises everyone and gives its top prize to a movie the consensus had more or less written off. Below are six of those nights, along with the voting rule that explains several of them and the reasons this kind of upset has nearly disappeared.

How Best Picture Votes Are Counted

Most Oscar categories are nominated by the matching branch, so directors choose the directing nominees and editors choose the editing ones. Best Picture works differently. Every member gets a say at the nomination stage, which means a makeup artist’s ballot counts exactly as much as a famous producer’s.

About 10,000 people vote in total, and nothing in the rulebook says what makes a film the best. The Academy spells out in detail which movies qualify and where they have to screen, but once a title is in the race, it all comes down to taste. Since the 98th ceremony there has been one new condition: members can only vote in a category’s final round if they have watched every nominee in it.

How the votes get counted matters even more. For the 2009 film year, the Academy doubled the Best Picture field from five nominees to ten, and many people connected that move to ‘The Dark Knight’ missing out on a nomination the year before. The bigger field also brought back the preferential ballot, a method the Academy had used in its early decades. Here is how it works:

•  Voters don’t pick one favorite. They rank all the nominees, from the one they like most to the one they like least.
•  When no movie has more than half of the first-place votes, the one with the fewest gets knocked out.
•  Its ballots then go to whichever title each voter ranked next, and the counting keeps going until a nominee crosses 50%.

In practice, a movie that lands second or third on lots of ballots can beat one that half the Academy adores and the other half puts near the bottom. You don’t need a huge crowd of passionate fans to win, because being liked by almost everyone is enough. That is bad news for divisive films, which are often the ones critics get most excited about.

Upsets Under the Old Single-Choice Ballot

For several decades before 2009, things were simpler: each member picked one Best Picture nominee, and whichever got the most votes won. Two of the most famous upsets happened under that system, so ranking math played no part in them.

1999: ‘Shakespeare in Love’ Over ‘Saving Private Ryan’

Going into the 1999 ceremony, ‘Saving Private Ryan’ had the Golden Globe for Best Drama and the top awards from both the producers’ and directors’ guilds. Steven Spielberg did win Best Director that night. The big prize, though, went to ‘Shakespeare in Love’, a light romantic comedy set in Elizabethan London, and the result still comes up whenever people argue that the Academy prefers charm to a hard-hitting war film.

2006: ‘Crash’ Over ‘Brokeback Mountain’

By the time the 2006 Oscars came around, Ang Lee’s ‘Brokeback Mountain’ had collected pretty much every major prize going. There was the Golden Lion from Venice, then the Golden Globe for Best Drama, then the BAFTA, and Lee himself won Best Director earlier that evening. Nobody seemed ready for what Jack Nicholson read out from the last envelope: ‘Crash’. Looking back, Paul Haggis’s film had a couple of things on its side. It had won the Screen Actors Guild ensemble award, and actors are the biggest group inside the Academy. It was also a movie about Los Angeles, the city where a good share of the voters live and work.

Upsets Under the Preferential Ballot

All four of the later upsets came after ranked voting returned, and they follow a similar pattern. The favorite had plenty of devoted supporters, while the winner was simply ranked higher by more of the Academy.

2017: ‘Moonlight’ Over ‘La La Land’

No Best Picture moment is better known than the 2017 mix-up, when Warren Beatty and Faye Dunaway announced ‘La La Land’ and the mistake was only fixed on stage minutes later. Damien Chazelle’s musical had every reason to look like a winner: 14 nominations, which tied the record, a record seven Golden Globes, the BAFTA and the producers’ and directors’ guild awards. The trophy went to ‘Moonlight’, Barry Jenkins’s three-part story of a young man growing up in Miami, and analysts have since argued that the musical split voters while ‘Moonlight’ sat high on many ballots that did not have it first.

2019: ‘Green Book’ Over ‘Roma’

‘Roma’, Alfonso Cuarón’s black-and-white memory of 1970s Mexico City, arrived at the 2019 ceremony with the BAFTA and the directors’ guild award. Cuarón went home with Best Director, Best Cinematography and Best Foreign Language Film, yet Best Picture went to ‘Green Book’, which had won the producers’ guild prize. It is hard not to read that result as a warm, easy-going road movie collecting more high rankings than a slow and demanding drama.

2020: ‘Parasite’ Over ‘1917’

A year later, Sam Mendes’s ‘1917’ looked safe after winning the Golden Globe, the BAFTA and both the producers’ and directors’ guild awards. Bong Joon-ho’s ‘Parasite’ had taken the actors’ guild ensemble prize instead, and on Oscar night it became the first non-English-language film ever to win Best Picture. The dark comedy about a poor family working its way into a rich household turned out to have much broader support among Academy members than the consensus had assumed.

2022: ‘CODA’ Over ‘The Power of the Dog’

‘The Power of the Dog’ went into the 2022 ceremony with 12 nominations, more than any other film, along with the Golden Globe for Best Drama, the BAFTA and the directors’ guild award, and Jane Campion did win Best Director. ‘CODA’ had just three nominations and was a remake of a French comedy-drama about a hearing girl in a deaf family, with the American version moving the family to a fishing town. Late in the season it won the producers’ and actors’ guild awards, and on the night this gentler, less divisive film came out ahead of Campion’s cold, slow western.

How Each Upset Night Ended

Here is how those six nights looked side by side:

In three of the six cases the favorite won at least as many Oscars as the Best Picture winner, and ‘La La Land’ took twice as many as ‘Moonlight’. The Academy often shared its awards among several films and kept the biggest one for the title with the widest support.

Why Best Picture Upsets Have Become Rare

‘CODA’ was the last genuine shock, and even that one did not come completely out of nowhere, since its late guild wins gave observers several weeks to catch up. Every Best Picture race from 2023 through 2026 went to the frontrunner. ‘Everything Everywhere All at Once’ and ‘Oppenheimer’ both dominated the guild awards, ‘Anora’ won the producers’ and directors’ prizes before its 2025 win, and ‘One Battle After Another’ took home six Oscars in 2026, Best Director among them.

A few things about the current system keep pushing the race toward consensus:

•  With ten nominees, first-place votes get spread thin, so broad support counts for more than passionate devotion.
•  The preferential count favors whichever title the fewest voters put near the bottom.
•  Guild voters overlap with Academy members, so the long guild season shows where the consensus lies early on.
•  The  Academy now requires members to watch every nominee before voting, which should make their rankings more complete.

What the Old Upsets Still Show

Not every category has become predictable, and the acting and craft races can still throw up a surprise. Best Picture is a different story now, because the system rewards the steady, widely liked contender over the bold one that splits the room. The upsets from 1999 to 2022 feel like they belong to an earlier era of the race, and Jack Nicholson’s raised eyebrows as he read out ‘Crash’ are still the best reminder of what those nights were like.