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32 Most Outrageous MTV VMAs Moments of All Time

From Miley’s twerk to Eminem being a jerk, the craziest highlights from the ceremony’s wild past

Britney Spears and Madonna - 2003 VMAs Kiss

Madonna and Britney Spears shared an iconic kiss at the 2003 MTV Video Music Awards.

Christopher Polk/Getty

Since their 1984 debut, the Video Music Awards have thrived on being the unpredictable younger sibling of America's awards-show family — and their penchant for causing headlines and shaking up the pop music world hasn't diminished. Here are 32 moments from VMAs past that have caused tongues to wag and eyebrows to raise. 

MTV VMAs

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12

Prince’s Butt Getts Cheeky (1991)

Prince's orgiastic demonstration of Diamonds and Pearls-era hit "Gett Off" lasted nearly seven minutes. Pity the VMAs viewer checking their watch for even a second as the funky pop icon illustrated 23 positions in a one-night-stand wearing a ventilated yellow suit that left nothing to the imagination. Even on a flame-filled, multi-tiered stage filled with musicians and writhing dancers, Prince's lithe movements and muscular guitar work remained the focus — especially once a few spins made it abundantly clear that his suit had holes in the seat to showcase his butt. "Let me show you, baby, I'm a talented boy," he sang.

MTV VMAs
11

Diana Ross Meets Lil Kim’s Cleavage (1999)

Lil Kim made a splash at the 1999 ceremony, with an electric purple wig that matched her much-chattered-about-outfit — a jumpsuit that dipped below her left breast, allowing it to roam free with only a pastie encumbering it. When Diana Ross came out to present Best Hip-Hop Video with Kim and Mary J. Blige, she was so enamored with Kim's willingness to show skin that she skipped the customary, "Hi, how are you" hug and went straight for her co-presenter's cleavage, giving it a jiggle that induced a big laugh from its recipient.