The 20 biggest Oscar upsets of all time

Ang Lee’s gay cowboy romance Brokeback Mountain was one of the most acclaimed films of 2004. At the time, it was groundbreaking in its representation and featured stellar performances from two of Hollywood’s biggest stars, Heath Ledger and Jake Gyllenhaal. Everybody was certain that it would snag Best Picture, so it came as a complete shock when race relations drama Crash won out of nowhere. Some believe that Academy voters were too conservative to vote for Brokeback. 

The upset of Moonlight winning Best Picture at the Oscars wasn't so much about the film itself as about the way the situation unfolded. At the 2017 Oscars, Warren Beatty and Faye Dunaway announced La La Land as the Best Picture winner, after the film had already won seven awards that night. The cast and crew came onstage, only for someone to realise that the wrong card had been read out. Barry Jenkins’s Moonlight had actually won the top award, spinning everyone in the room. 

The Academy is usually known for handing out Oscars to actors in more dramatic roles, with comedies often sidelined. That is why it came as a delightful surprise when Marisa Tomei, a newcomer at the time, took home Best Supporting Actress for her hilarious work in My Cousin Vinny in 1993. Tomei hadn’t won any previous awards during the season, and was up against veteran actors like Joan Plowright, Vanessa Redgrave, and Miranda Richardson. 

Despite having won a Golden Globe and BAFTA, Olivia Colman was definitely not the favorite (no pun intended) to win the Oscar for Best Actress in 2019 for The Favourite . Everyone’s money was on Glenn Close to win for her performance in The Wife, after having been nominated six times previously. However, Colman ended up winning the prize, leaving Close Oscar-less once more. It was also the only award that The Favourite took home that night, despite several nominations.

In 2020, South Korean film Parasite broke records and made Oscars history by becoming the first foreign-language film to win Best Picture. Director Bong Joon-Ho’s class warfare satire transcended language barriers and connected to audiences all over the world, becoming one of the most acclaimed films of the century. It beat massive movies like The Irishman, Once Upon a Time in Hollywood, Joker and many more. Joon-Ho also won Best Director to top it all off.

In 1999, Steven Spielberg’s war epic Saving Private Ryan was set to win the Oscar for Best Picture. Spielberg had won Best Director, and the film featured an all-star cast led by Tom Hanks. So it came as quite a shock when period romance film Shakespeare in Love won instead. Many agree that Saving Private Ryan was unquestionably the superior film, but Shakespeare in Love had the upper hand thanks to now disgraced movie mogul Harvey Weinstein’s forceful campaigning strategies.  

Adrien Brody may now be a two-time Oscar winner, but in 2003, he was still an underdog. At age twenty-nine, he was up against previous winners Jack Nicholson, Michael Caine, Nicolas Cage, and Daniel Day-Lewis, and unbelievably won. Acting great Day-Lewis was the heavy favourite, but Brody’s harrowing turn in Holocaust drama The Pianist was too exceptional to ignore. Brody remains the youngest recipient to ever win Best Actor at the Oscars. 

Some people need a whole movie to showcase their acting skills to win an Oscar, but Beatrice Straight only needed five minutes. In the film Network , Straight played Louise, the wife of a network television executive. She delivered such a powerhouse performance in such a short time that she snagged the Best Supporting Actress gong. It is a remarkable achievement, especially considering who she was up against, which included Jodie Foster for Taxi Driver and Piper Laurie for Carrie.

In 2020, we lost the great Chadwick Boseman, who gave his last on-screen performance in Ma Rainey’s Black Bottom. After posthumously winning a Golden Globe and SAG Award, it seemed fitting that Boseman would receive the Oscar in one final moving tribute. It was even set up that way, with Best Actor being presented last instead of Best Picture. That is why it was quite confusing and anticlimactic when Anthony Hopkins in The Father was announced as the winner.  

Usually, an Oscar winner receives a number of accolades beforehand, but that wasn’t the case for the 2001 Best Supporting Actress winner, Marcia Gay Harden. Harden’s nomination for her role in Pollock was a surprise in itself, as she had been excluded from the Golden Globes, Critics' Choice Awards, SAGs, and BAFTAs. It is one of the only times where an Oscar winner hadn’t won, let alone been nominated, at all the previous big award shows. 

At age eleven, Anna Paquin defied odds when she won the Oscar for Best Supporting Actress for her role in The Piano. She had only previously been nominated for a Golden Globe, so her win came as a surprise, especially given her young age. Paquin is the second youngest Oscar winner ever, and won against heavyweights like Holly Hunter (her The Piano co-star, from whom she often steals the show throughout the film), Rosie Perez, Winona Ryder, and Emma Thompson. 

Citizen Kane is often regarded as the greatest movie ever made. Yet, it missed out on the Oscar for Best Picture in 1942. That honor went to How Green Was My Valley, a small and poignant family drama that people know only as the film that beat Citizen Kane. At the time, Kane proved to be a remarkable feat in filmmaking, revolutionizing the movie industry thanks to its themes and technological choices. It has stood the test of time, unlike Valley, which is still a great film regardless. 

In true underdog fashion, just like its titular boxer, Rocky took home the award for Best Picture at the 1977 Oscars. At the time, Sylvester Stallone was relatively unknown and burst onto the scene with this film. The sports drama, which laid out many of the conventions for future sports films, impressively beat other titles like Taxi Driver, All the President’s Men, and Network. Rocky has stood the test of time, with sequels and spin-offs that prove why it is so enduring. 

One of the most delightful upsets in Oscars history was Italian actor Roberto Benigni's Best Actor win in 1998 for Life is Beautiful . In the film, Benigni delivered an uplifting yet heartbreaking performance as a Jewish man who uses humour and imagination to shield his son from the horrors of the Holocaust. As an actor in a foreign language film, the win came as a surprise, beating Tom Hanks and Edward Norton. Benigni also memorably climbed over seats to reach the stage and accept his award. 

In 2009, cinema’s highest-grossing movie of all time, Avatar, was released. The box-office juggernaut and technical achievement changed the moviegoing landscape and was expected to sweep the Oscars in 2010. However, it was Kathryn Bigelow’s war drama The Hurt Locker that stole Avatar’s thunder and won both Best Picture and Best Director. Bigelow was the first woman to ever win Best Director, while The Hurt Locker was the first Best Picture winner to be directed by a woman. 

In 2024, Hollywood legend Demi Moore staged a major comeback with her boundary-pushing lead performance in the film The Substance. When she was nominated for an Oscar, many believed she would win the award and finally get her flowers after decades in the industry. However, it still wasn’t Moore’s time, as twenty-five-year-old Mikey Madison won the Best Actress prize for her performance as a sex worker in the 2025 Best Picture winner Anora. 

Lauren Bacall is one of the most iconic actresses of Hollywood’s Golden Age, and unbelievably did not receive an Oscar nomination until 1997 for her supporting role in The Mirror Has Two Faces. After over half a century in the industry, the acting legend was expected to finally get her long-overdue recognition. However, the big film of that night was The English Patient, so Juliette Binoche won the award instead, spoiling a fairy-tale ending in the making. 

In 1982, British sports drama Chariots of Fire won Best Picture over Warren Beatty’s film Reds, which earned twelve nominations and was the favorite going into the ceremony. While Chariots of Fire was a highly acclaimed film at the time, it has lost some momentum over the years, being remembered mostly for its epic, triumphant soundtrack by Vangelis. It even beat Raiders of the Lost Ark, which has become one of the most timeless movies ever made.

One of the more confusing Oscar wins was Grace Kelly's Best Actress win for The Country Girl in 1955. Kelly is undoubtedly a Hollywood legend, but her two other films released that year, Rear Window and Dial M for Murder, are far superior to The Country Girl. What’s even more puzzling is that Judy Garland was expected to win for A Star Is Born, so the network sent a camera crew to the hospital where she had just given birth so she could give an acceptance speech. 

In 2013, Ang Lee won the Oscar for Best Director for Life of Pi. Pi is a gorgeous piece of cinema, so his win wasn’t a huge surprise. What was most surprising was the glaring snub of Ben Affleck in the category, who directed the Best Picture winner that year, Argo. Leading up to the Oscars, Affleck had won every major directing award, including the Golden Globe, BAFTA, Critics' Choice, and DGA. The fact that he wasn’t even nominated for an Oscar is baffling.