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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
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.

MTV VMAs
10

Rage Against the Machine’s Tim Commerford Climbs the Walls (2000)

Rage Against the Machine walked a thin line as political rabble-rousers who also indulged in show business spectacle — basically, the most anti-capitalist group to appear on the Godzilla soundtrack. But that fragile balance finally seemed to collapse in 2000, when the band performed at the VMAs and competed with Limp Bizkit for the Best Rock Video award. When Bizkit won, RATM bassist Tim Commerford (then going by the timely nickname "Y.tim.K") interrupted Fred Durst's acceptance speech by climbing up on the stage's scaffolding. Commerford spent the night in jail, and Rage frontman Zach de la Rocha was reportedly so disgusted by his antics that it helped spur the band's breakup soon after.