9 Oscars Winners Who Don't Hold Up to the Test of Time

Just because a movie or a celebrity wins an Oscar, that doesn’t mean the win was deserved. While the Academy Awards are seen as the capstone to awards season — and one of the highest honors in the business — we all know that stars and movies get snubbed or overlooked all the time.

What’s worse is when we look back at what did win, and shake our heads in confusion and disbelief. So, with the 89th Academy Awards just around the corner, let’s take a look back over the show’s illustrious history at a few times the Academy voters clearly made a mistake.

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1. How Green Was My Valley wins Best Picture at the 14th Academy Awards in 1942

Photo: 20th Century Fox

Beat Out:
Citizen Kane, The Maltese Falcon, Blossoms in the Dust, Here Comes Mr. Jordan, Hold Back the Dawn, The Little Foxes, One Foot in Heaven, Sergeant York, Suspicion

What Should Have Won:
Citizen Kane

Citizen Kane
is at or the near the top of every single list of Best Movie lists written in the last half-century. However, when it came out, Newspaper magnate William Randolph Hearst (whom the film is loosely based on) railed against it so hard, he forced nearly every critic in the country to bash it in their papers and fought to get it buried. Over 70 years later, his efforts didn’t work and it remains one of the most groundbreaking films ever made. Meanwhile, How Green Was My Valley was also a movie that existed, even if you’ve never heard of it. So who really won?

2. John Wayne wins Best Actor Oscar for True Grit at the 42nd Academy Awards in 1970

Photo: Paramount Pictures

Beat Out:
Dustin Hoffman in Midnight Cowboy, Jon Voight in Midnight Cowboy, Richard Burton in Anne of the Thousand Days, Peter O’Toole in Goodbye, Mr. Chips

Who Should Have Won:
Dustin Hoffman in Midnight Cowboy

John Wayne only ever played himself, and while True Grit might have been one of his better films, he didn’t lose himself in the role the way Hoffman and Voight did in their timeless, heartbreaking drama. This was Wayne’s only Oscar, but many think he barely should have been nominated at all.

3. Art Carney wins Best Actor for Harry and Tonto at the 47th Academy Awards in 1975.

Photo: 20th Century Fox

Beat Out:
Dustin Hoffman in Lenny, Jack Nicholson in Chinatown, Al Pacino in The Godfather Part II, Albert Finney in Murder on the Orient Express.

Who Should Have Won:
Jack Nicholson in Chinatown

Remember Art Carney’s timeless performance as an old man who travels around with his cat? Of course you don’t. Carney winning the Oscar over Jack Nicholson remains one of the most baffling Academy choices of all time, and is hard evidence that, sometimes, even a performance that cements your presence in the pantheon of Hollywood icons can lose to an cute old man and his pet.

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4. Rocky wins Best Picture at the 49th Academy Awards in 1977

Photo: United Artists

Beat Out:
Network, Taxi Driver, All the President’s Men, Bound for Glory

What Should Have Won:

is, without a doubt, one of the best boxing movies of all time. In fact, it’s one of the best sports movies of all time. However, Network, Taxi Driver and All the President’s Men are three of the best movies period, no genre modifier required. In fact, the freighting, prophetic story of reality TV and yellow TV journalism told in Network stands as a testament (and warning) to this very day. Although Rocky had six sequels (if you include Creed), so maybe it’s not our place to judge.

5. Al Pacino wins Best Actor for Scent of a Woman at the 65th Academy Awards in 1993

Photo: Universal Pictures

Beat Out:
Robert Downey Jr. in Chaplin, Denzel Washington in Malcolm X, Clint Eastwood in Unforgiven, Stephen Rae in The Crying Game

Who Should Have Won:
Denzel Washington in Malcolm X or Clint Eastwood in Unforgiven

There are so many other performances Al Pacino deserved to win the Oscar for. In fact, he was nominated seven times before he won, for his astounding turns in The Godfather, Serpico, The Godfather Part II, Dog Day Afternoon, …And Justice for All., Dick Tracy (for some reason), and Glengarry Glen Ross. After his win for Scent of a Woman, he never got another nomination. What does that tell you? This scenery-chewing mess was just the Academy’s mea culpa for snubbing him so many times before. Any other year, and maybe that would have been fine, but screwing over Washington and Eastwood wasn’t fair.

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6. Shakespeare In Love wins Best Picture at the 71st Academy Awards in 1999

Photo: Miramax Films

Beat Out:
Saving Private Ryan, The Thin Red Line, Elizabeth, Life is Beautiful

What Should Have Won:
Saving Private Ryan

Shakespeare In Love
was a fun, feel-good movie, and sometimes that’s all it takes to win over Academy voters when the competition are all gritty, depressing war dramas (and a less-fun, but far better, English period piece). But happy doesn’t necessarily mean best, and it’s clear now that Steven Spielberg’s intense Saving Private Ryan should have walked away with the gold.

7. Roberto Benigni wins Best Actor for Life Is Beautiful at the 71st Academy Awards in 1999

Photo: Miramax Films

Beat Out:
Tom Hanks in Saving Private Ryan, Edward Norton in American History X, Ian McKellen in Gods and Monsters, Nick Nolte in Affliction

Who Should Have Won:
Edward Norton in American History X or Tom Hanks in Saving Private Ryan

While no one is diminishing Benigni’s performance in the Holocaust dramedy, but the whole thing wears thin with the hindsight of Benigni’s tiring persistence at being funny and wacky in real life — like when we he jumped across the theater seats to accept his Oscar. Meanwhile, Norton’s frightening, powerhouse performance in American History X and Hanks’ weather worn and uncharacteristically forlorn presence in Saving Private Ryan had far more nuance and have held up all these years later.

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8. Crash wins Best Picture at the 78th Academy Awards in 2005

Photo: Lionsgate

Beat Out:
Brokeback Mountain, Capote, Good Night, and Good Luck, Munich

What Should Have Won:
Any of them other than Crash

Remember how, days after Crash won the Oscar, we all started looking back at that obvious mistake the way a person wakes up after a bender in Vegas and struggles to understand what happened or why they did what they did? The ham-fisted and laughable attempt to tackle topics of racism and bigotry (which ended up just being kind of racist), stole the Oscar from Brokeback Mountain. But really, any of its competitors should have walked away with the gold instead.

9. Sandra Bullock wins Best Actress for The Blind Side at the 82nd Academy Awards in 2010

Photo: Warner Bros. Pictures

Beat Out:
Carey Mulligan in An Education, Gabourey Sidibe in Precious, Meryl Streep in Julie & Julia, Helen Mirren in The Last Station

Who Should Have Won:
Carey Mulligan in An Education or Meryl Streep in Julie & Julia.

Everybody loves Sandra Bullock, but Carey Mulligan’s turn in An Education was a revelation, and Meryl Streep’s portrayal of the celebrity chef Julia Child was easily the star’s greatest portrayal of a real-life icon. Streep went on to win her third Oscar for playing Margaret Thatcher in The Iron Lady two years later, but many think she stole that award from Glenn Close for her role in Albert Nobbs or Viola Davis in The Help.

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