10 Surprising Oscar Upsets - Warped Factor - Words in the Key of Geek.

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10 Surprising Oscar Upsets

The Oscars, or the Academy Awards, have been synonymous with recognizing cinematic excellence for nearly a century. While these prestigious awards usually honor the most deserving films and performances, they have also seen their fair share of surprises and upsets over the years. In this retrospective, we will explore ten Oscar upsets that left audiences and industry insiders shocked, debating the choices made by the Academy. From unexpected wins to controversial snubs, these moments continue to be discussed and debated by film enthusiasts worldwide.

1. Shakespeare in Love Wins Best Picture Over Saving Private Ryan (1999)

Date: March 21, 1999

In 1999, Steven Spielberg's World War II epic "Saving Private Ryan" was the clear frontrunner for the Best Picture category. Its visceral portrayal of D-Day and the horrors of war was hailed as a cinematic masterpiece. However, to the surprise of many, "Shakespeare in Love," a romantic period piece starring Gwyneth Paltrow and Joseph Fiennes, took home the top prize.

Justification: The upset victory of "Shakespeare in Love" over "Saving Private Ryan" is often cited as one of the most controversial decisions in Oscar history. While "Shakespeare in Love" was a charming film, many believed that the realistic and emotionally gripping "Saving Private Ryan" deserved the honor.

Retro Comment: "The Academy's choice of 'Shakespeare in Love' over 'Saving Private Ryan' will forever be debated. It remains one of the Oscars' most surprising and polarizing moments." - The New York Times

2. Crash Wins Best Picture Over Brokeback Mountain (2006)

Date: March 5, 2006

In 2006, "Brokeback Mountain," directed by Ang Lee, was hailed as a groundbreaking film for its portrayal of a same-sex love story between two cowboys. It was widely expected to win the Best Picture category, but "Crash," a film exploring racial tensions in Los Angeles, pulled off a stunning upset.

Justification: "Crash" winning Best Picture over "Brokeback Mountain" was met with shock and disappointment from many who saw the latter as a culturally significant film. The upset raised questions about the Academy's willingness to embrace LGBTQ+ narratives.

Retro Comment: "The 'Crash' upset will be remembered as one of the most surprising Oscar wins, leaving many to question the Academy's decision-making." - Entertainment Weekly

3. Rocky Wins Best Picture Over Taxi Driver (1977)

Date: March 28, 1977

Martin Scorsese's "Taxi Driver," a gritty exploration of urban alienation and violence, was a critical darling and considered a frontrunner for Best Picture in 1977. However, "Rocky," the underdog story of a boxer played by Sylvester Stallone, emerged victorious.

Justification: While "Rocky" is celebrated for its inspirational story, "Taxi Driver" is regarded as a cinematic masterpiece. The upset victory of "Rocky" raised questions about the Academy's preference for crowd-pleasing films over edgier, more challenging fare.

Retro Comment: "The Academy's choice of 'Rocky' over 'Taxi Driver' is a reminder that Oscar upsets can sometimes prioritize heartwarming narratives over bold and unsettling visions." - The Guardian

4. Ordinary People Wins Best Director Over Raging Bull (1981)

Date: March 29, 1981

Martin Scorsese's "Raging Bull" is widely regarded as one of the greatest films ever made, with Scorsese's direction praised as masterful. However, the Best Director Oscar in 1981 went to Robert Redford for "Ordinary People."

Justification: Scorsese's loss for "Raging Bull" is often cited as one of the most significant snubs in Oscar history. It left many questioning the Academy's appreciation for gritty, uncompromising filmmaking.

Retro Comment: "The omission of Martin Scorsese for 'Raging Bull' in the Best Director category remains a contentious point of discussion among cinephiles." - The New Yorker

5. Art Carney Wins Best Actor Over Al Pacino (1975)

Date: March 29, 1975

In 1975, Al Pacino was nominated for the Best Actor Oscar for his iconic role as Michael Corleone in "The Godfather Part II." Many believed it was a sure win for Pacino, but Art Carney's performance in "Harry and Tonto" secured him the award.

Justification: Al Pacino's loss to Art Carney remains one of the most surprising upsets in the Best Actor category. It sparked discussions about whether the Academy was biased against younger actors.

Retro Comment: "Art Carney's win over Al Pacino is a classic example of Oscar voters favoring seasoned actors over newcomers. It's a decision that still raises eyebrows today." - Variety

6. Adrien Brody Wins Best Actor for The Pianist (2003)

Date: March 23, 2003

In 2003, Adrien Brody won the Best Actor Oscar for his role in "The Pianist." While his performance was praised, the award was widely expected to go to Daniel Day-Lewis for "Gangs of New York."

Justification: Adrien Brody's win over Daniel Day-Lewis was a significant upset in the Best Actor category. It highlighted the unpredictability of the Oscars and the Academy's willingness to embrace breakthrough performances.

Retro Comment: "Adrien Brody's surprising win for 'The Pianist' remains one of the Oscars' most unexpected moments, proving that the Academy loves a good underdog story." - Entertainment Weekly

7. Dances with Wolves Wins Best Director Over Martin Scorsese for Goodfellas (1991)

Date: March 25, 1991

In 1991, Kevin Costner's directorial debut, "Dances with Wolves," was a surprise hit, both critically and at the box office. While Costner's achievement was commendable, it was widely expected that Martin Scorsese would finally win his first Oscar for directing "Goodfellas," a crime epic that had garnered immense acclaim.

Justification: The upset victory of Kevin Costner over Martin Scorsese in the Best Director category was a shocking turn of events. Scorsese had previously been nominated for Best Director several times without a win, and many believed "Goodfellas" would be the film to finally secure his victory.

Retro Comment: "Kevin Costner's win for Best Director was a major upset, as Martin Scorsese's 'Goodfellas' was seen as a masterpiece of modern cinema. The Oscars had once again eluded Scorsese." - Variety

8. Chariots of Fire Wins Best Picture Over Reds (1982)

Date: March 29, 1982

In 1982, Warren Beatty's epic film "Reds" was considered a frontrunner for Best Picture. However, the British drama "Chariots of Fire" took home the top honor.

Justification: "Chariots of Fire's" victory over "Reds" was viewed as a surprising decision, considering the latter's epic scope and critical acclaim. It raised questions about the Academy's preferences in storytelling.

Retro Comment: "The selection of 'Chariots of Fire' over 'Reds' for Best Picture left many puzzled, as Beatty's film was seen as a monumental achievement." - Los Angeles Times

9. My Fair Lady Wins Best Picture Over Dr. Strangelove (1965)

Date: April 18, 1965

In 1965, the Oscars featured a clash of cinematic styles and themes when "My Fair Lady," a lavish musical adaptation of George Bernard Shaw's "Pygmalion," went head-to-head with Stanley Kubrick's satirical black comedy "Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb."

Justification: "My Fair Lady's" win for Best Picture over "Dr. Strangelove" was a surprising choice, as Kubrick's film had gained notoriety for its biting humor and relevance during the Cold War era. While "My Fair Lady" was celebrated for its grand production and memorable music, "Dr. Strangelove" was seen as a groundbreaking work of satire.

Retro Comment: "The Academy's decision to favor the lavish musical 'My Fair Lady' over the razor-sharp political satire 'Dr. Strangelove' remains a testament to the diversity of cinematic genres celebrated at the Oscars." - The New Yorker

10. "Moonlight" Wins Best Picture Over "La La Land" (2017)

Date: February 26, 2017

In 2017, the Academy Awards featured a jaw-dropping moment when "La La Land" was initially announced as the Best Picture winner. However, in a historic turn of events, it was revealed that "Moonlight," a poignant coming-of-age drama directed by Barry Jenkins, was the actual winner.

Justification: The mix-up during the Best Picture announcement at the 2017 Oscars was one of the most unexpected and unforgettable moments in Academy Awards history. While "La La Land" had been a frontrunner throughout the awards season, "Moonlight" ultimately claimed the top prize, marking a significant upset.

Retro Comment: "The 'Moonlight' upset over 'La La Land' at the 2017 Oscars will forever be etched in Hollywood history as a moment of genuine surprise and triumph for a small, independent film." - The Hollywood Reporter


The Oscars, with their storied history of recognizing excellence in filmmaking, have also been marked by surprising upsets and controversial decisions. These moments of unpredictability and debate continue to remind us that, in the world of cinema, there are no guarantees. While some upsets are celebrated as triumphs of the underdog, others remain contentious topics of discussion among film enthusiasts.

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