The Just-As-Short-List: Top Ten Most Awkward Celeb Moments

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At some point we all suffer moments so painfully uncomfortable that we wish we could bore into our brains and suck out the memory with a shop-vac. But at least the cameras aren’t rolling when ours happen, unlike these unfortunate celebs. While memories may fade, video clips never do. That’s bad luck for them, but endlessly amusing for the rest of us.

Last Friday night The Short List train barreled on with the 10 Most Awkward Celebrity Moments. There were so many to choose from that we decided to chime in with a just-as-short-list of our own. You’ll laugh, you’ll cry, you’ll cringe, and for once you’ll be glad you’re not to be rich and famous. See if your favorite moment made the cut!

[Photo: Getty and Images]

10. BOB GELDOF CALLS RUSSELL BRAND A “C*NT”

After spending the last twenty-five years fighting poverty and famine, Bob Geldof decided to take on a slightly easier target at the 2006 NME Awards: host Russell Brand. Granted, Brand did refer to him as “Bobby Gandolf,” but jeez…was he accepting the Bono Award for “Excellence in Taking Yourself Way Too Seriously?” Russell’s face as he shakes Geldof’s hand says it all. Oof.

9. TOM GREEN AVENGES HIS DESK

Tom Green was a pioneer in the art of guerrilla annoyance. This is the man who painted his parent’s house plaid, put a dead cow’s head in their bed and sprayed a XXX lesbian sex scene onto the hood of their car. So when guest Jessie James Dupree walked onto The New Tom Green Show with a chain saw in 2003 and proceeded to hack Green’s desk, we assumed he’d be totally down. Wrong. His response created a incident of Jerry Springer proportions. Dupree proved so wildly unlikable that we find ourselves siding with the guy who has a history of humping road kill. Weird.

8. JANICE DICKINSON ON THE RAMPAGE

This terrifying clip never fails to get our heart racing. Outside an LA restaurant in April 2009, the self proclaimed “Original Super Model” leaped at photographers like a swishy raptor who had downed a couple bottles of Cristal. Your move, Spielberg.

7. FAITH HILL IS A SORE LOSER?

Award shows are always a treasure trove of awkward celebrity oopsies. Blink and you’ll miss this priceless moment from Faith Hill at the 2006 Country Music Awards. She has since claimed that her angry outburst was a joke. Even if that’s true, it’s still not as funny as the prank they pulled at last years CMA’s. Remember, when Taylor Swift won all those awards? That was HILARIOUS! Good one, guys.

6. MCCAIN SKIPS LETTERMAN FOR COURIC

Busted. If you’re gonna lie and blow off one of the most popular TV hosts in the country, it’s generally not a good idea to then wheel down the street and appear live on different show instead. Especially when they’re on the same network. That’s like calling in sick from work and then having a picnic in the cubical next to your boss’ office. But that’s exactly what John McCain did in September 2008. We’re not saying this affair directly contributed to McCain’s defeat, but there’s a toll man on the road to the White House and his name is Dave Letterman. Throw this one on the Stupid Human Tricks pile.

5. CHRIS BROWN AT THE BET AWARDS

You know the feeling you get when there’s a stranger crying in the bathroom stall next to you? Yeah, watching Chris Brown’s meltdown at the 2010 BET Awards is kind of like that.

4. ELTON VS. LILY

Can you feel the love in this clip? Because we can’t. The spat between Lily Allen and Elton John at the 2008 GQ Awards is just plain ugly. We don’t care how trashed you are, you do NOT tell The Rocketman to “f*ck off” unless you want one of his old rhinestone-studded platform boots up your rear. Let’s hope she sent him a couple greenhouses of flowers to apologize.

3. MARIAH CAREY TWEAKS OUT


Mariah Pre-Breakdown
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Way back in 2001 Mariah Carey proved that Glitter is hazardous to your health. That’s probably why it tanked at the box office. At the time there was much speculation that between touring, recording and filming her cinematic debut, the soulful songstress was working herself into a nervous collapse. When you hear this bizarre free-association word salad recorded before an in-store appearance, it’s hard not to agree.

2. ASHLEE SIMPSON ON SNL

Who could forget the moment that the junior Simpson Milli-Vanilli’d her way into our hearts? She may not have been singing in this 2004 Saturday Night Live appearance, but those dance moves were more than worth it. According to legend, the jig was taught to her by a leprechaun, who later tricked her and stole her original nose.

1. KANYE CARES

Kayne West has been responsible for more than his fair share of awkward celebrity moments. But this clip from the 2005 telethon to benefit victims of Hurricane Katrina sets the standard. It has everything. Incredibly inappropriate timing. Racial tension. A stumbling and clearly improv’d speech. Mike Myers‘ horrified head turn. The camera cut to a bewildered Chris Tucker. Although coming close at last year’s VMA’s, Kayne has never been able to equal this pinnacle of discomfort.