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Our Favourite Videos of People Embarrassing Themselves at the Oscars

It's hard out here for an Oscar winner.

by Dave Schilling
02 March 2014, 9:18am

Photo via Flickr user Doug Kline

The Academy Awards is my favourite day of the year here in Los Angeles. It's without a doubt the coolest event in the world that takes place inside a shopping mall, even cooler than the "Rock the Mall" series at Sierra Vista Mall, in Clovis, Calfornia, and LA Fashion Week at the Grove. Since I've never gone to the Academy Awards, and I can't confirm whether or not Wetzel's Pretzels is open during the event, but I like to stay up daydreaming about Brad Pitt grabbing a Sinful Cinnamon with a side of caramel dipping sauce before the show starts.

Of course, copping a treat could lead to an awkward situation. You could spill caramel on your tux. The camera could catch you with pretzel in your teeth. You might get stuck in line and miss your name being called. The Oscars are watched by millions of people every year, and any slip-up – pretzel-related or otherwise – could be devastating to your reputation. Nevertheless, some people don't care and throw caution to the wind, staying true to their wacky personal brand (or drug-induced mania), even in their greatest moment of professional triumph. In honour of those brave souls who just don't give a damn, here are some of the most cringe-worthy moments in Oscar history.

– Anna Paquin's first taste of the spotlight came thanks to her Best Supporting Actress win for The Piano, in 1994. I feel bad making fun of her for her stunningly ugly outfit, since she was at the tender age of 11 when she won, and it wasn't really her fault she cosplayed as the Old Lady Who Lives in a Shoe: The Early Years. It was her parents' fault for dressing her as if Whoopi Goldberg from Star Trek: The Next Generation and Kevin Costner in Waterworld had a baby that resembled a slightly uglier Olsen twin. MEMO TO ANNA PAQUIN'S PARENTS: She still hates you for making her wear an Irish peasant dress from the 25th century on the most important day of her life.

–  The Best Original Song award is the real wild card of the night. Prince and Eminem have won, and Ray Parker Jr., South Park's Trey Parker, Dolly Parton, Counting Crows, Elliot Smith, Jon Bon Jovi and Sting (three times!) have all been nominated. And no one can ever take that away from any of them; "Academy Award nominee Ray Parker Jr." does not give a shit you think he's a joke as long as you play the theme from Ghostbusters at least once every Halloween.

Anything goes in this category, and thank God for that, because Three 6 Mafia has an Oscar. The group responsible for the best song ever about drinking cough medicine for fun has an Oscar. That's not embarrassing on its surface, but when you watch this video and peel back the layers, you see that something is very amiss. Was "3/6M" an inside job? Probably not, but...

First of all, Queen Latifah presenting the award is almost too perfect. She's also a hip-hop artist who was nominated for an Oscar. Secondly, why are they already onstage when the award is announced? If they lost, would they have just turned around and sulked back to their seats, Charlie Brown–style? Why do the producers seem to only be cutting to the black people in the crowd? Finally, at about 1:48 in the above video, DJ Paul just starts making noises with his mouth that I am positive are not actually words, but are some Illuminati code to our alien overlords to commence the invasion of Earth. Was he having a mild stroke? Did he hit that lean too hard knowing he was going to win?

I guess conspiracy theories are meaningless because "George Clooney, my favourite. He show me love when I first met him" might be the most memorable acceptance speech quote in Oscar history.

– "What? You said what? The president did what? Aw, man. Hey, that's all good, baby. He got rid of the player haters too? Aw, man. We need to declare this a national holiday. We gonna call this player's holiday. Ant Beezy, what's up, mang?"

– There's a good chance that you've never seen the 2009 Academy Award winner for Best Documentary Short, Music by Prudence. It tells the story of Prudence Mabhena, a disabled woman from Zimbabwe who overcame her country's systemic prejudice against the physically handicapped through the power of her music. In the history of cinema, that film will always be eclipsed by the above moment of insanity: Elinor Burkett, a producer of the movie who had a falling out with director Roger Ross Williams over the film's creative direction, wandered onto the stage and interrupted Williams during his acceptance speech, leading to an entire nation simultaneously screaming, "Why is my grandma at the Oscars?"

–It seems like every year there's at least once totally unexpected "novelty black person" nominated for an Oscar. I don't mean to say "novelty" as a way of demeaning their acting accomplishments, I say it because it's almost always someone you've either (A) never heard of or (B) not associated with acting talent. Quvenzhané Wallis was not a professional actor. Jennifer Hudson was best known as "that girl who got eliminated from American Idol." Morgan Freeman's been nominated a bunch of times, and every time I'm like, "Who dat old man fo' realz?"

Nothing will ever top brash comedian Mo'Nique's winning Best Supporting Actress Oscar for her role in Precious. Her work was stellar and infinitely memorable, but no one was expecting such skill from her. She came out of nowhere to win that award, and she hasn't done much of note since. You could chalk that up to the problems facing black actors in Hollywood – add on the fact that she's plus-sized and a woman, and you have the trifecta of traits that the industry discriminates against. You could also blame her weird acceptance speech, in which she decries the now standard awards-season politicking, which she loudly rebelled against the whole year leading up to the event. Also, am I the only one who laughed when she thanked BET?

–This is, without a doubt, the most embarrassing moment in Oscar history. It only could have been worse if they had given the Best Picture award to Seven Cans of Unexposed 16mm Film, A Box of Used Tissues, or Santa Clause 3: Escape Clause. Pause at the 3:08 mark to bask in the horrified look on the face of Steven Spielberg as reality starts to wash over him. I'd rather watch the Screech sex tape than sit through Crash again. The only difference between the two is I have never masturbated while watching Crash.

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