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Still Starstruck: The Biggest Upsets in Academy Awards History

Underdogs Celebrated While Rest of the World Gasped

Last year, favorites cleaned house during the Academy Awards. All but two of the 23 categories saw the chalk come away on top, leading to a rather uneventful show if we go by the Academy Awards predictions.

But once in a while, a massive upset or two will steal the show. We look back at some of the most shocking upsets that are still talked about today.

95th Oscars along Hollywood Boulevard during preparations for the Academy Awards - Patrick Fallon/AFP
95th Oscars along Hollywood Boulevard during preparations for the Academy Awards - Patrick Fallon/AFP

Best Picture Upsets Still Upset People Today

Moonlight Won Over La La Land… By the Way (2017)

Who can ever forget about the kerfuffle during the 89th Academy Awards? Just as La La Land’s crew were accepting their award, it was announced that Moonlight actually won. It’s an infamous moment that still lives in people’s minds today.

But as far as the Academy Awards picks were concerned, the film was as large as a +650 underdog on the betting lines, becoming one of the largest upsets in Oscars history by this merit alone.

Yo, Adrian” Rocky Won! (1977)

Rocky is one of the best feel-good movies ever. The film is so influential it basically spawned an infinite amount of underdog sports movies in its wake. So it’s only fitting that it found a way to win Best Picture against the likes of Network and Taxi Driver, which were more critically acclaimed.

Network also dominated on the evening, winning four Oscars, including the Best Original Screenplay and both leading actor awards. Had there been online gambling lines here, Rocky would have been a sizable underdog.

Shakespeare in Love Got the Academy Lovestruck (1999)

Some Best Picture wins age like milk and Shakespeare in Love beating out Saving Private Ryan at the 71st Oscars is one of them. Steven Spielberg’s classic war film dominated other awards like the Golden Globes. But thanks to Miramax’s “overly aggressive campaigning”, they convinced enough members of the Academy to vote for this romantic period piece.

A 2015 poll then indicated that Academy voters regret voting for Shakespeare in Love and would vote for Saving Private Ryan instead if given a chance to redo it. Still, those underdog bets online had already been cashed, and the results remain the same today.

Honorable Mentions:

  • How Green Was My Valley over Citizen Kane (1942)
  • Braveheart over Sense and Sensibility and Apollo 13 (1996)
  • Crash over Brokeback Mountain (2006)

Acting Category Stunners: The Who Won?!

The Father Did Not Bless Chadwick Boseman’s Night (2021)

This is a relatively fresh upset, and in terms of the Las Vegas odds, Anthony Hopkins was as large as a 7-1 underdog to win. It had been a foregone conclusion that the recently departed Chadwick Boseman would bring home the Best Actor award for his brilliant performance in Ma Rainey’s Black Bottom. Some books even had Boseman as a -5000 favorite.

The Academy even switched up the presentation order leaving this for last in a gesture to honor his life and legacy. This was supposed to be a moment dedicated to the young actor whose career and life ended too soon. So it was understandable to see people incensed when it was Hopkins’s name that was announced. To rub salt into the wound, he was not even present to accept the award.

Kate Hudson Was Almost Famous (2001)

The supporting actor categories can cause as much of a shock as their leading counterparts. None felt as big as in the 73rd Academy Awards when Marcia Gay Harden upset Kate Hudson. Harden starred in Pollock, which was one of the lesser-known films at the ceremonies. While she had a strong performance, there were little-to-no indications she would beat out Hudson.

Then 22 years old, Hudson was baptized as the next big Hollywood star for her performance in Almost Famous. She took home the Golden Globe along with a plethora of awards. Her only notable loss came at the Screen Actors Guild (SAG) Awards to Judi Dench of Chocolat. Unfortunately for Hudson, the Academy did not quite love her as much as everyone else did.

Olivia Colman Was The Favorite, Not Glenn Close (2019)

Just two years before Anthony Hopkins made stunning Academy Awards news, The Favourite’s Olivia Colman pulled off a similar feat. The Englishwoman was +650 on the betting lines to upset the large favorite, Glenn Close, who was listed at -625. This was supposed to be Close’s night.

Alas, it was yet another “so close yet so far” moment for The Wife star, who remains one of the greatest actresses without an Oscar today.

Also, if you’re the sort of person who’s practically glued to the couch in a TV series binge-watching marathon, you’ll be thrilled to know that we’ve got futures odds for the show ‘Renfield‘. So come on, grab your popcorn, and prepare to be amused!

Honorable Mentions:

  • Adrien Brody (The Pianist) over Daniel Day-Lewis (Gangs of New York) and Jack Nicholson (About Schmidt) (2003)
  • Roberto Benigni (Life is Beautiful) over Tom Hanks (Saving Private Ryan) and Edward Norton (American History X) (1999)
  • Alan Arkin (Little Miss Sunshine) over Eddie Murphy (Dreamgirls) (2007)

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