Flavor Flav
Flavor Flav (pictured with Queen Latifah) put together an ensemble for the 1990 show that included not only his signature clock necklace but also golf-themed hat, shirt, pants and shoes; pink bat-wing sunglasses; and a pack of beer.
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Howard Stern
Image Credit: Photo Credit: Getty Images Boxers or briefs? Neither for Howard Stern, who got cheeky in 1992 with an outfit that proudly displayed his rear end. The look was completed with wing-tip — literally — gold boots.
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Lady Gaga
Image Credit: Photo Credit: Getty Images The pop singer wore a complete outfit — dress, headpiece and shoes — made out of meat for last year's show. She later said the getup had many meanings. "If we don't stand up for what we believe in and if we don't fight for our rights, pretty soon we're going to have as much rights as the meat on our own bones. And, I am not a piece of meat." The dress was recently put on display at the Rock & Roll Hall of Fame in Cleveland.
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Ke$ha
Image Credit: Photo Credit: Getty Images The singer actually made her own outfit for the 2010 VMAs. "I got the garbage bags from Home Depot and I kind of just put it together," she said about her black dress.
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Tommy Lee and Pamela Anderson
Image Credit: Photo Credit: Getty Images Sparkles, sequins, feathers — the Baywatch actress had it all in her red-carpet ensemble in 1999. Her date, then-husband Lee, opted for a more casual look, sporting a baggy overcoat and braids.
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Macy Gray
Image Credit: Photo Credit: Getty Images The "I Try" singer wasn't above doing some self-promotion in an attempt to drum up interest in her forthcoming second album, The Id. In 2001, she wore a customized dress that read, "MY NEW ALBUM DROPS SEPT. 18, 2001," on the front and "BUY IT!" on the back.
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Andy Dick
Image Credit: Photo Credit: Getty Images The actor-comedian spoofed Christina Aguilera in her Dirrty phase with his head-to-toe pink ensemble in 2001 and blond pigtails with pink highlights. The belly-baring outfit also featured roller skates and — apparently safety was a concern — elbow and knee pads.
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Lil’ Kim
Image Credit: Photo Credit: Getty Images The rapper took the one-shoulder trend to new depths in 1999 when she wore a one-piece jumpsuit and purple pasty. The outfit was completed with a matching wig.
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Christina Aguilera
Image Credit: Photo Credit: Getty Images Long before she became a coach on The Voice, where she raised eyebrows with her cleavage-bearing outfits, Aguilera was wearing even less clothing. In 2002, the pop singer sported a demin skirt and very revealing top.
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Mudvayne
Image Credit: Photo Credit: Getty Images Mudvayne arrived at the 2001 show in white suit jackets, black ties, black pants — and blood-soaked faces, nearly calling attention away from their multicolored, architectural mohawks.
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Rose McGowan
Image Credit: Photo Credit: Getty Images The actress managed to upstage her date, then-boyfriend Marilyn Manson, with her see-through outfit, which was comprised merely of some chainmail in the front and chains in the back. She was topless and wearing only a G-string underneath, leaving very little to the imagination.
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Britney Spears
Image Credit: Photo Credit: Getty Images Hell's angel? The pop singer channeled bikers when she chose this leather-and-lace outfit in 2002.
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Jack Black
Image Credit: Photo Credit: Getty Images The actor channeled the King of Pop, Michael Jackson, in his Bad stage, when he wore this in 2003.
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Missy Elliott
Image Credit: Photo Credit: Getty Images Golf, anyone? The rapper got decked out in green-and-yellow plaid Adidas — including a pompon-adorned hat — at the 2003 show.