The 10 Worst Winners In Oscar History

Let’s be clear – the upper echelons of Hollywood are dominated by weirdos, losers and mutations. I’m not judging – I live in LA, so naturally some of my best friends are weirdos, losers and mutations. I’m simply pointing out a fact. Most of the normal, hardworking, all-American folks in Hollywood are crew – and they showed it with their heartfelt booing of Michael Moore when he removed the muffin from his pie-hole just long enough to run down our country during the 2003 Oscar ceremony.

But these great Americans are generally not members of the Academy of Motion Picture Arts and Sciences, and they don’t get to vote for who takes home the Oscar. People like Sean Penn do. And Tim Robbins. And tranny vomit recipient Susan Sarandon.

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These are the kind of folks who make up the majority of Oscar voters, so it’s no wonder that the Academy Awards show is so often a festival of nitwittery that leaves normal Americans scratching their heads wondering, “Um, what the hell was that?”

Oscar has more than its share of astonishing failures, of crazy-uncle-locked-in-the-attic nods that the Academy sorely regretted about the time the after-party coke bowls ran dry. The terrible Oscar choices listed here are only from the last few decades since the sting of choosing How Green Is My Valley over Citizen Kane and The Maltese Falcon has presumably faded since 1941– well, for some of us. Oh, and you won’t find Marisa Tomei on this list – she rocks. Deal with that, haters.

So, in no particular order of insanity, here are Oscar’s 10 biggest recent screw-ups: ]



1. Crash: Best Picture 2006: Before Paul Haggis annoyed the Scientologists, he annoyed most of the rest of the world with Crash, a ponderous stew of liberal guilt and condescension that lucked into a Best Picture Oscar through a combination of pinko button pushing and the pure dumb luck of having an equally tiresome raft of competing nominees.

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With fellow nominees Brokeback Mountain, Munich, Capote, and Good Night and Good Luck, Crash was up against sodomy, moral equivalence, more sodomy and George Clooney. Apparently, the voters found Crash the lesser of five mediocrities.

2. Shakespeare In Love: Best Picture 1999: Well, I guess I’m just being petty. I mean, Saving Private Ryan was merely a stirring, technically magnificent tribute to the unbelievable bravery of the heroes who stormed the beaches at Normandy and freed Europe from the grip of Nazi tyranny. But Shakespeare In Love was about show business and it also displayed Gwyneth Paltrow’s epically unimpressive rack. So I guess it was an easy choice for the Academy – they got to pick a flick about Actors and Acting while also dissing those dirty brutes who do Army stuff. To pat themselves on their collective backs and diss the proles – how could they pass up that opportunity? Well, they couldn’t, and they didn’t.

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Now, there’s nothing really wrong with Shakespeare In Love. It’s a perfectly serviceable film if you happen not to have testes, or merely hate all they stand for. Sure, there are some guys out there who think a topless Gwyneth from 14 years ago is sexy, but movies need to appeal to more than just lonely shut-ins whose life partners are manufactured by the Kleenex Corporation. This condescending, anti-American snob is to hot women what her husband’s band Coldplay is to cool music,and she needs to stick to her goop.com blog where she comments on the everyday problems that real moms face, like uppity butlers and “tiara hair.” Enough said about her.


In ambition and execution, Private Ryan – a film I have my problems with – was so manifestly superior artistically and technically that to overlook it could not simply be a mistake. The electrifying initial landing scene is so unforgettable that it alone justified a Best Picture award regardless of what came after. No, there had to be an agenda. And that’s what makes this choice more than just risible – it was despicable.

3. Al Pacino in Scent of a Woman: Best Actor 1993: Oh, how the mighty have fallen. From his iconic roles in the 70’s like Michael Corleone to the bizarrely over-the-top but unforgettable Tony Montana in the 80’s, you could always count on Al to deliver. But this? It’s bad enough that it came to this; it’s worse that the Academy acted as an enabler to Pacino’s sad decline into tedious caricature.

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Hooah? I don’t think so.

4. Roberto Begnini in Life Is Beautiful: Best Actor 1999: This award was so manifestly undeserved that it made President Obama’s Nobel Peace Prize seem as underwhelming as a third place middle school science fair ribbon tossed at Albert Einstein. Let me put this out there – Life Is Beautiful is perhaps the stupidest, most offensive major motion picture ever made. When the Nazis came looking for Begnini, this holocaust comedy literally had people in the audience yelling, “Hey, he’s hiding in the alley!”

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Someone told Roberto Begnini a terrible lie – that he was amusing. In fact, he is the most annoying performer in the entire history of cinema, a history that includes Matt Damon and Channing Tatum. What takes him to a whole new level of suck is that he thinks he’s hilarious, which he is – in the same way a giant herpetic lesion is hilarious.

The “wacky” English-mangling acceptance speech he offered when presented with this award was brilliant…to those who hit the sauce in their limos beforehand. For the rest of the audience, it was like a root canal sans anesthetic, but without the fun. Fortunately, Begnini has faded into well-deserved obscurity and his movies are today largely forgotten, a tribute to the collective human mind’s ability to block out traumatic experiences.

5. Alan Arkin in Little Miss Sunshine: Best Supporting Actor 2007: “Let’s honor a trangressive indie comedy where the grandpa swears and drinks and does drugs – yeah, that’ll blow the collective minds of those squares out there in Jesusland!” Such was no doubt the thought process that went into handing the little gold naked guy to veteran Alan Arkin for what was essentially playing the same curmudgeonly character he’d been essaying since the great Freebie and the Bean. Now, that was an amusing, truly un-PC movie:

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So rent Freebie and let Little Miss Sunshine fade into a vague, unpleasant memory.

6. Diablo Cody for Juno: Best Original Screenplay 2008: Once again, the Academy experienced the equivalent of a “double bagger,” where it wakes up in the morning, looks at what it brought home, and asks “What the hell was I thinking?”

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Juno is not the most horrible movie of all time, despite the presence of the spirit-killing Michael Cera and Ellen Page and a soundtrack full of crappy, waify hipster alt-folk songs that are so twee they make Justin Beiber seem like Megadeth. It’s just that Juno is embarrassingly pretentious, with the precocious heroine’s vocabulary packed with painfully cutesy words like “shenanigans.” And when Rainn Wilson’s character calls her “home skillet,” well, you just want to slap him.

This is the problem with a novelty act movie – the Academy is amused for a few minutes, votes it an Oscar, then spends the rest of eternity shaking its collective head after figuratively sobering up.

7. An Inconvenient Truth: Best Documentary 2007: It’s hard to believe that it was only four years ago that people actually believed in global warming. But it’s not hard at all to believe that among the biggest suckers were the pampered quarter-wits who do most of the Academy Award voting. Al Gore’s ridiculous exercise in propaganda, delivered with the subtlety of a sledgehammer, was a natural choice for the Oscar voters, but they were probably pretty disappointed they couldn’t also vote for the nominated documentary that dissed Christians or the other one that trashed America over Iraq. Whoever said that Hollywood doesn’t embrace a diversity of thought?

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In any case, An Inconvenient Truth is destined to be the Reefer Madness of 2007, with stoned UC Berkeley students from the Class of 2032 laying around their dorms laughing at how stupid people were back in the mid-aughts. Well, some people.

8. The English Patient: Best Picture 1997: Perhaps the Academy wanted some balance after properly awarding the magnificent Schindler’s List Best Picture in 1994, which is the only possible explanation for why this over-praised, under-interesting celluloid atrocity could have won. After all, this is the film that seriously posits that collaborating with the Nazis is perfectly cool if it will help you score with a mediocre chick who happens to be married to some other dude.

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Sure, we can’t expect the film’s mere utter moral bankruptcy to dissuade the Academy voters – these are the folks who think Roman Polanski is the real victim. But couldn’t they at least notice that this soapy melodrama is about the most boring way to spend nearly three hours outside of a Meet the Press marathon?

9. Kate Winslet in The Reader: Best Actress 2009: What the hell is it with Hollywood and Nazi sympathizers? Well, admittedly Kate Winslet’s character had more going for her than just cavorting with brownshirts – she was illiterate and liked to do underage boys. In Hollywood, that’s like an acting trifeca, and Kate went the full fascist-illiterate-pedo.

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Oh, the performance itself? Um, I have a question: How did Kate Winslet get tagged as some sort of great thespian revelation? In every movie she is in, she always seems to bear the same furrowed-brow, vaguely troubled expression, as if she was suffering from mild indigestion. It must be something else – perhaps her willingness to doff her clothes and display her chubby charms in pretty much everything she’s been in. Whatever.


10. 3-6 Mafia’s “Hard Out here For A Pimp”: Best Song 2006: Perhaps the most hilarious pick of all time, the Academy’s choice of the year’s Best Song from the rap/hooker extravaganza Hustle & Flow was just awesome. For once, the saccharine Disney ditties and the generic pop hits were thrust aside in favor of a gritty urban tune that finally dared to musically explore the difficulties that industrious entrepreneurs face in their daily lives. Yeah, nothing like a song we can all relate to.


Most amazing were the hip hop stylings of those past and future unknowns, 3-6 Mafia, cavorting on stage while a bunch of dancers dressed like Hollywood’s idea of “hos” gyrated and frolicked before the bejeweled and bewildered audience:

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Simply spectacular. Yeah, it sure is hard out here for a pimp who’s trying to get his money for the rent. Who can’t identify with that? Especially in Hollywood.

And this year, Oscar, don’t forget to keep your pimp hand strong!

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