The Worst Best Picture Oscar Winners Since 1990

Updated on June 24, 2020
Noel Penaflor7 profile image

I've been a movie enthusiast my whole life and been writing movie reviews for over 14 years.

Produced by Harvey Weinstein. You let it happen.
Produced by Harvey Weinstein. You let it happen.

Why since 1990 only? Because that’s what the movie overlords instructed me to do. Perhaps another article will go further back, but probably not.

If you’re reading this after the Academy awards nominations were announced, the awards season has officially begun…way back in December.

If you’re reading this after the Oscar telecast is over, that was an exciting awards season, wasn’t it? Full of thrills and surprises, especially when (INSERT exciting thing that happened) or when (INSERT shocking thing that happened that you totally didn’t expect). Man, I did not see that second thing coming.

As with everything subjective, some will be worse than others. Sometimes, most of the time, it’s only time that can truly determine which movie that won was actually best, and which movie that won was W…T…F.

Keep in mind, that none, well, most of the movies on this list aren’t necessarily bad, but there’s no way it deserved the Best Picture of the Year Oscar. Some of them we knew then, some of them took years for us to realize something else should have won. If Driving Miss Daisy won your Oscar office pool back in 1990, well then good on you. That still doesn’t mean it should have ever won Best Picture over Born on the 4th of July, it doesn’t matter how many times Magical Negro Morgan Freeman drove the old lady around the block.

In no particular order, these are the worst Best Picture Oscar Winners since 1990.

Best Picture Winner 1995: Forest Gump

The world will never be the same, once people start quoting fortune cookie wisdom from Forrest Gump.
The world will never be the same, once people start quoting fortune cookie wisdom from Forrest Gump.

Why The F*ck Did This Win Best Picture?

Syrupy sweet nostalgia. A soundtrack every person was required to buy (on CD no less) in 1994. Groundbreaking special effects at the time. Tom Hanks’ Oscar Winning Best Actor performance as the mildly mentally challenged lovable doofus who miraculously triumphs over history with some of the most trite one-liners in movie history (“Something, something box of chocolates”). Someone even gets to die of AIDS, which was a staple of Tom Hanks movies back in the early 90s. If you were around when Gump hit theaters then you rode the wave, but after the credits rolled you needed to drink a gallon of water to get all the sugar out your mouth.

Other Nominees
Four Weddings and a Funeral
Quiz Show
Pulp Fiction
The Shawshank Redemption

What Should Have Won?

Pulp Fiction

Pulp Fiction. Pulp Fiction. Pulp Fiction. 25+ years later and every movie fan knows Pulp Fiction got robbed. Quentin Tarantino cribbed every grindhouse picture from his formative years, and still managed to come up with something wholly original. Even if you don’t remember or care who won Best Picture in 1995, you still remember Pulp Fiction. It doesn’t matter that Quentin Tarantino hasn’t topped himself since. Even Quiz Show and The Shawshank Redemption have more resonance than Forrest Gump.

Buy Pulp Fiction Here!

Pulp Fiction [Blu-ray]
Pulp Fiction [Blu-ray]
The Best Movie of 1994!

Best Picture Winner 1999: Shakespeare in Love

You're invited to a screening of this alone in a soundproof room with Harvey Weinstein. No one can hear you scream.
You're invited to a screening of this alone in a soundproof room with Harvey Weinstein. No one can hear you scream.

Why The F*ck Did This Win?

Because Academy Voters are/were old and white and a trifle like Shakespeare in Love was the safest possible choice. It’s a decent enough movie and Gwyneth Paltrow deserved her Best Actress Oscar, but there’s a reason so many people were shocked when Harrison Ford called its name instead of Saving Private Ryan. Because it didn’t deserve to win.

Other Nominees
Saving Private Ryan
The Thin Red Line
Life is Beautiful

What Should Have Won?

Saving Private Ryan

Looking down on that one guy from above.
Looking down on that one guy from above.

As you might have guessed from the previous paragraph, Saving Private Ryan. You didn’t really need to guess, because Saving Private Ryan is one of the greatest movies of all time and Shakespeare in Love is just an asterisk. You can’t and don’t really want to imagine what Harvey Weinstein did to get Shakespeare in Love produced, let alone win Best Picture. Ewww.

Best Picture Winner 2006: Crash

Is Don Cheadle pimpin' on you?
Is Don Cheadle pimpin' on you?

Why Did This Win?

Because we are all connected…or something like that. Not as simplistic as that, but this hyperlink movie relies on one too many coincidences that are supposed to be revelatory but end up making you cringe. Harkens back to a time when Brendan Fraser had movies actually end up in theaters. And it has Ludacris. Still a very good movie, but 2005 gave us so much more.

Other Nominees
Good Night and Good Luck
Brokeback Mountain

What Should Have Won?

Brokeback Mountain

Brokeback took risks and is one of the best love stories of the century. Munich is Steven Spielberg’s most thrilling movie of the 2000s. Either one of them should have taken the gold that night, but Oscar voters wanted their Very Important Lessons spoon fed.

Best Picture Winner 2011: The King's Speech

Seriously? Why Did This Downton Abbey Prequel Win?

Because it’s got British people in it with British accents and even a Hitler cameo. If you add Brits, it automatically makes it more award-worthy than something that takes an actual risk. Plays like a generic sports movie with the hero scoring the winning goal at the last second. Colin Firth s-s-s-stutters his way to an Oscar and white people are so excited this wins.

Other Nominees
Black Swan
The Fighter
Toy Story 3
The Kids Are All Right
127 Hours
Winter’s Bone
The Social Network
True Grit

What Should Have Won?

The Social Network

The Social Network as a movie still matters today, even if it’s not for the best of reasons. In a movie that’s mostly dialogue, every frame of David Fincher’s best film since Fight Club feels alive, while the King’s Speech still feels like the BBC logo should be emblazoned at the corner of the screen.

Best Picture Winner 2009: Slumdog Millionaire

*eyes roll*
*eyes roll*

Why The F*ck Did This Win?

People like a happy ending, even if you do spend the final 20 minutes rolling your eyes. It even has a Bollywood dance number at the end. How cute. And by “How cute”, I mean, “Shoot me now.” The movie undercuts every genuine moment of pathos with that cloying and mawkish ending. One of the worst Best Picture Winners ever in one of the worst movie years ever.

Other Nominees
The Reader
The Curious Case of Benjamin Button

Worst Best Picture Nominee of the Past 30 Years

The Reader.

A navel gazing self-important homework assignment that manages to combine a Holocaust awards bait movie with an illiteracy awards bait movie. It wouldn’t have been so bad if it this didn’t take the spot of…

What Should have Won?

The Dark Knight

The best movie of 2008 wasn’t even nominated for Best Picture because it was a comic book movie. You remember back in 2008, a time before the risk-averse Marvel movies saturated giga-plexes, A time when Robert Downey Jr. played Iron Man only once. TDK is still the best comic book movie of the modern era and still echoes in the collective memory more than that movie with Jeopardy in it.

Closing Thoughts

Thanks for taking a trip with me to some of the worst Best Picture Oscar Winners since 1990. I couldn’t have done it without you because you were kind enough to allow me to use your internet connection when you weren’t home. Be sure to vote below.


What’s Your Least Favorite Best Picture Winner?

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    • Noel Penaflor7 profile imageAUTHOR

      Noel Penaflor 

      5 months ago from California

      Most of the winners you haven't seen are pretty good movies, but "Best" does not apply.

    • profile image

      Jacqueline G Rozell 

      5 months ago

      Apologies for sounding as though I am on a loop here but haven't kept up with Academy Awards since the year "Gandhi" beat "Tootsi" for the thing. Dustin Hoffman was so good, when he was playing Tootsie, I forgot it was a man playing a woman, and felt that "woman" was going to get an Oscar as a supporting character. A wooden statue could have played the Gandhi character. As for the movies receiving the Oscar mentioned here, I have seen none of them, not even Forest Gump. Those mentioned as the "should have" winners, I saw them all.


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