The Oscars, Hollywood’s most prestigious award ceremony, have always been a platform for glitz, glamour, and excellence in cinema. However, amid the predictable winners, some moments have left both the audience and critics stunned.
Upsets and underdog victories at the Oscars are moments when a nominee defies expectations, beating out more popular contenders to claim the golden statue. These unexpected triumphs often go down in history, sparking conversations that last for decades. Below, we explore the most surprising upsets and underdog victories in Oscar history, moments when David triumphed over Goliath in the world of cinema.
The 1999 Oscars: Gwyneth Paltrow vs. Cate Blanchett
One of the most discussed upsets occurred in 1999 when Gwyneth Paltrow won the Best Actress award for her role in Shakespeare in Love. Many believed Cate Blanchett, who had delivered a commanding performance as Queen Elizabeth in Elizabeth, was a shoo-in for the win. Blanchett’s portrayal of the historical monarch was hailed as one of the year’s most powerful performances. Paltrow’s role, while charming and light-hearted, lacked the dramatic intensity of Blanchett’s. Still, Paltrow took home the Oscar, leaving many wondering if the Academy had opted for charm over substance. This upset continues to be one of the most talked-about moments in Oscar history.
Adrien Brody Steals the Show in 2003
The 2003 Academy Awards brought another major upset when Adrien Brody won Best Actor for his role in The Pianist. He beat out heavyweights like Daniel Day-Lewis (Gangs of New York) and Jack Nicholson (About Schmidt), both of whom were considered frontrunners for the award. Brody’s deeply emotional performance as a Jewish musician struggling to survive during the Holocaust in Roman Polanski’s film touched the hearts of audiences worldwide. His victory, though unexpected, felt well-earned, making it one of the more celebrated upsets in recent Oscar history.
Marisa Tomei’s Surprise Win in 1993
No discussion about Oscar upsets would be complete without mentioning Marisa Tomei’s 1993 victory. Tomei won Best Supporting Actress for her comedic performance in My Cousin Vinny. She beat out seasoned actresses like Judy Davis, Joan Plowright, Vanessa Redgrave, and Miranda Richardson—all of whom were nominated for more dramatic and traditionally “Oscar-worthy” roles. Tomei’s win surprised critics and viewers alike, leading to rumors that her name had been called by mistake. Decades later, her victory is still debated, though Tomei has since proven herself as an accomplished actress, silencing much of the skepticism.
Crash Wins Best Picture in 2006
Perhaps one of the most controversial upsets in Oscar history came in 2006, when Crash won Best Picture over Brokeback Mountain. Brokeback Mountain, a groundbreaking film about a romantic relationship between two cowboys, was widely considered the favorite. It had already won numerous accolades leading up to the Oscars, including the Golden Globe and BAFTA awards for Best Picture. Crash, on the other hand, was a racially charged ensemble drama that tackled social issues in modern-day Los Angeles. Its victory sparked immediate backlash, with many accusing the Academy of playing it safe and avoiding a film with LGBTQ+ themes. The debate surrounding this upset continues to this day, with many still feeling that Brokeback Mountain was robbed of its rightful win.
Shakespeare in Love Triumphs Over Saving Private Ryan
In 1999, the Best Picture category saw one of the most surprising results in Oscar history. Shakespeare in Love defeated Steven Spielberg’s war epic Saving Private Ryan, which had been the frontrunner from the start. Spielberg had already taken home the Best Director award, and many expected Saving Private Ryan to follow suit with Best Picture. However, the lighter, romantic period piece Shakespeare in Love, with its witty dialogue and clever depiction of William Shakespeare’s early career, won the night. While both films were critically acclaimed, Saving Private Ryan’s groundbreaking war scenes and emotional depth made it seem like the more obvious choice. This upset has been analyzed and debated for years, with some speculating that Miramax’s aggressive marketing campaign helped swing the vote in favor of Shakespeare in Love.
The King’s Speech Beats The Social Network in 2011
In 2011, The King’s Speech pulled off a major upset, winning Best Picture over the much-hyped The Social Network. David Fincher’s film about the creation of Facebook was expected to sweep the Oscars, especially after dominating the earlier awards season. Its sharp screenplay, innovative direction, and strong performances made it a favorite among critics and audiences alike. However, the Academy opted for the more traditional The King’s Speech, a historical drama about King George VI and his struggles with a stutter. While both films were excellent, The King’s Speech’s win was seen by many as the Academy favoring a more conventional narrative over a contemporary, cutting-edge story.
Olivia Colman’s Shocking Best Actress Win in 2019
The 2019 Oscars brought a shocking upset in the Best Actress category when Olivia Colman won for her role in The Favourite. Most people had expected Glenn Close to finally win her long-overdue Oscar for her performance in The Wife. Close had been nominated seven times before and had been the favorite to win that year. Colman’s portrayal of Queen Anne, while brilliant and layered, was not considered a frontrunner, which made her win all the more surprising. Colman’s heartfelt and humorous acceptance speech only added to the charm of her unexpected victory.
Spotlight Triumphs Over The Revenant in 2016
The 2016 Best Picture race seemed all but decided when Alejandro González Iñárritu’s survival epic The Revenant swept the major categories at earlier award shows. With Leonardo DiCaprio finally securing his long-awaited Oscar for Best Actor, many believed The Revenant would also take home the top prize. However, in a shocking twist, the investigative journalism drama Spotlight won Best Picture. The film, which tells the true story of how journalists at The Boston Globe uncovered the Catholic Church sex abuse scandal, was praised for its ensemble cast and meticulous storytelling. Its victory over The Revenant was seen as a win for substance over spectacle, making it one of the most surprising and satisfying upsets in Oscar history.
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