50 Craziest VMA Outfits

Most awards shows find movie stars, singers, and other entertainers trying to top each other with the most glamorous, classic dresses and tuxes in the world. But MTV's annual Video Music Awards have always been a showdown of outre apparel. From Outkast in shaggy Snuffleupagus pants and Wonka-orange lederhosen to Christina Aguilera using a scarf-like apparatus to, uh, lift and separate; to Mudvayne in formal white dinner jackets with bloody bulletholes in their foreheads: MTV's red carpet has hosted it all. And no one will soon forget Lady Gaga's red lace face-covering, undies-showing dress.

With this year's VMA's just around the corner on Sept. 12, there's no better time to look back at 50 of the most daring, bear-all, wacky and way-out costumes of music's hottest stars from the VMAs' 26 year history.

The bottle in Kanye West's hand served as an outrageous accessory in 2009, considering what happened with Taylor Swift once the VMAs kicked off inside.

Dancehall artist Elephant Man is a ray of blinged-out sunshine at the 2004 VMAs.

Body glitter is expected more of female attendees than male rockers at the VMAs, but Tyson Ritter of The All American Rejects embraced the trend in 2009.

Carmen Electra was careful how she sat, stood and generally moved at the VMAs in '97.

Prince could join the Blue Man Group with his look at the '99 VMAs.

Aerosmith's Steven Tyler lost a fight with a clothes dryer at the '87 VMAs, as he debuted a shrunken look.

Funk legend Bootsy Collins and guitar hero Steven Van Zandt make an oddly-dressed odd couple at the 1991 VMAs.

MC Hammer also needed double-sided tape at the 1990 VMAs.

Madonna shows off her ink -- temporary, of course -- in 1998.

Howard Stern gave VMAs attendees and viewers an outfit they hoped to immediately forget in 1992.

Tommy Lee had the potential to be more revealing than his wife Pamela Anderson at the '99 VMAs.

Sheryl Crow showed her cowgirl side in 2001.

Rap group Digital Underground channeled their roots at the 1990 VMAs -- and threw in a pink shag coat for good measure.

Janet Jackson wasn't afraid to show her inner freak in 1995 at the VMAs.

DJ Fatman Scoop went from bed to red carpet in virtually no time in 2008.

Martha Stewart was kind enough to lend Busta Rhymes an outfit for the 1997 VMAs.

Andy Dick channeled a certain "Dirrty" singer at the 2001 VMAs, but his dance moves on those roller skates weren't exactly up to par.

Looks like Van Halen vocalist David Lee Roth came to the 1984 VMas straight from a trip to Hawaii.

Jessica Simpson attempted to turn on the sex appeal in 2005, but she just looked like she lost half of her dress.

Swedish garage rockers The Hives were certainly on everyone's radar back in 2002, but in case attendees weren't aware, the band made it easy at the VMAs that year.

Macy Gray proved than fashion is more than just a form of expression in 2001 -- it's also a form of promotion.

Lisa Marie Prestley would make her daddy proud with her rebel look at the VMAs in 2002.

Jennfer Lopez's 's barely-there ensemble created an interesting proportion against her floppy, oversized hat in 2001.

B2K's hippie warrior garb at the 2002 VMAs lives on -- even when the group doesn't.

Evanescence vocalist Amy Lee couldn't decided between naughty or nice looks in 2003, so she just wore both.

Devo meets diva in Piggy Hilton's 2009 VMAs outfit.

When Hayley Williams of Paramore is with her bandmates, she's just one of the boys. That showed in 2007 at the VMAs.

It's no surprise who Taboo of the Black Eyed Peas voted for in the 2008 election after his appearance at the VMAs that year.

The members of TLC rocked matching mermaid-inspired outfits at the '99 VMAs.

Flavor Flav, pictured here at the 1990 VMAs, is a simple man to please -- beer, golf and giant clock necklaces are all he needs.

Lil Mama looks more like child than mother at the VMAs in 2009.

At least Rodman rocked the red AIDS ribbon on his train wreck of a look in 1995.

Let's hope Missy Elliot, pictured here in at the 2003 VMAs, didn't use her MTV Moon Man to tee off.

Katy Perry was a "teenage dream" with her vintage Barbie look at the 2008 VMAs.

Slipknot looked slightly respectable in their suits and ties at the VMAs in 2008.

Before Gwen Stefani was a fashionista, she was "just a girl" in '98 -- who had blue hair and futuristic skirts.

Fergie's hat is reminiscent of "A Clockwork Orange," but the rest of the outfit screams saucy schoolgirl at the 2006 VMAs.

Lenny Kravitz's 1998 single "Fly Away" wasn't joking, but the rocker didn't prove it until six years later at the VMAs.

How could Shakira even sit down in those skin-tight leather pants is the outrageous part of her outfit at the 2001 VMAs.

Jack Black is a not-so-"smooth criminal" at the 2003 VMAs, ripping off Michael Jackson's look with more humor than style.

Destiny's Child channels a Native American vibe at the VMAs in 2001. It's more Dances With Beyonce than "Dances With Wolves."

Pink -- at her most, well, pink -- rocks leopard and gold for a wild child look at the 2000 VMAs.

His eyebrows might be the most surprising part of Axl Rose's sporty look at the 2001 VMAs.

Lil Kim was as brave as they come in 1999, letting it all hang out.

Big Boi and André 3000 of Outkast somehow make furry pants and orange overalls look good at the 2001 VMAs.

Schoolgirl no more. Britney Spears debuted her biker side at the 2002 VMAs.

For once, Mudvayne's brightly-colored mohawks were not the most eye-catching part of the band's appearance, pictured here in 2001.


Christina Aguilera definitely needed double-sided tape in order to avoid a "wardrobe malfunction" at the 2002 VMAs.

For once, Marilyn Manson, pictured here in 1998 with then-girlfriend Rose McGowan, is not the center of attention.

Lady Gaga showed off her many, many sides at the 2009 VMAs.