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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. 

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8

Eminem Beefs with Moby and Triumph the Insult Comic Dog (2002)

Eminem and Moby were already at odds following the electronica hero's accusations of homophobia and misogyny in Em's lyrics. With the artists only a few seats apart, tension built throughout the night. After shoving Triumph the Insult Comic (a.k.a. Robert Smigel's puppeted hand) out of his face, the war of words with Moby continued when the rapper took the stage to accept Best Male Video for "Without Me." "That little Moby girl threw me out of my zone," Slim Shady said, and was met with boos. "Keep booing, little girl. I will hit a man with glasses." However, Triumph might've gotten the last laugh at a "press conference" afterwards (wearing a tiny neckbrace). "Everyone, please. Let's all try to be easy on Eminem. At the end of the day, he's just another white guy trying to make an honest living… stealing black people's music."

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7

Michael Jackson and Lisa Marie Presley Kiss (1994)

"Just think, nobody thought this would last," said Michael Jackson at the time. And it didn't. But before his brief marriage to Elvis Presley's daughter concluded, the pair awkwardly made their love public to start the 1994 VMAs. He wore an outfit that was part bullfighter and part Mike Piazza, and she wore her second thoughts. The kiss itself proved less stilted than the laborious standing around on stage leading up to it, and far less perplexing than the toga party the couple staged later for MJ's "You Are Not Alone" video.

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6

Madonna Performs “Like a Virgin,” Writhes in a Wedding Dress (1984)

Herbie Hancock won the most MTV Video Music Awards in the show's inaugural year, but it was Madonna who made history. Posed as a life-sized bride figurine on a 17-foot cake, her Madgesty surprised the Radio City Music Hall crowd with "Like a Virgin," the title single (and eventual Hot 100 Number One) from an album still two months away from release. Willing the cameras to marry her for life, the 26-year-old Ms. Ciccone playfully spun, rolled and added a few choice thrusts while draped in the same mix of lace and punk bling — including a "Boy Toy" belt buckle — that would grace her album cover. According to French designer Maripol, her stylist at the time, the performance came from "kind of a vision I had." This idea emerged after the initial plan to sing the song to a full-grown Bengal tiger was scrapped.

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5

Pee-Wee Herman, Beleaguered Self-Pleasurer, Is in on the Joke (1991)

Paul Reubens had a rough summer in 1991. He'd already taken a break from playing his most famous character, Pee-Wee Herman, for over a year, worried that his cult comedy creation had taken over his career. And then, after he was arrested for masturbating in a Florida adult movie theater that July, the fallout began. CBS pulled reruns of Pee-Wee's Playhouse, Toys "R" Us took his toys off the shelves and his mugshot became a pop-culture meme. But after a couple months of being on the receiving end of endless wisecracks, Reubens took the stage at the VMAs with five words that proved he still had a sense of humor: "Heard any good jokes lately?"

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4

Andrew “Dice” Clay Is Banned for Life (1989)

It's hard to know what else the MTV brass was expecting when they put X-rated comedian Andrew "Dice" Clay on live TV for three minutes to introduce Cher. He went ahead and debuted two of his infamous "dirty nursery rhymes" (including "Rockabye baby on the treetop/Your mother's a whore, I ain't your pop") and said two of George Carlin's "seven dirty words you can never say on television" for good measure. The Diceman was banned from MTV after that night, and his career hasn't exactly thrived enough to give them any reason to reconsider. However he did reappear in a memorable sketch for the 1992 VMAs, making fun of the whole fiasco.

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3

Howard Stern’s Fartman Blows Hot Air (1992)

Howard Stern was still climbing onto his throne as the self-proclaimed King of All Media when the radio shock jock decided to use the 1992 VMAs as a launching pad for a movie franchise. Fartman, a character originated in the pages of The National Lampoon in the Seventies and hijacked by Stern in the Eighties, was ready for primetime, and Stern followed Prince in the tradition of male butt-cheeks proudly on display at the VMAs. But the flatulent comedy routine didn't go over well on MTV, and Stern's dreams of a Fartman movie were quickly scuttled. The character still found its way into movie theaters, however, when a reenactment of Fartman's awkward coming out party became the opening scene in Private Parts, the movie based on Stern's autobiography.

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2

Kanye West Interrupts Taylor Swift (2009)

We'll never know how much (or little) the trajectory of Taylor Swift's brilliant career shifted because of a hot-tempered Kanye West snatching her mic amid her Best Female Video acceptance speech. Nor can we see where Kanye West would be today if he hadn't yelled "Imma let you finish, but Beyoncé had one of the best videos of all-time!" before stalking off. And what of Queen Bey masking her disbelief in the audience? All already hyper-famous when it went down, the roles the trio have played before and since were all distilled in that moment. The five ensuing years yielded some of the finest creative output of their careers, but those awkward moments still loomed nearly as large via apologies, rebuffs, lines drawn and teams formed.

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1

Madonna Kisses Britney Spears and Christina Aguilera (2003)

Nineteen years after Madonna's iconic "Like a Virgin" performance, the stage was set with a wedding cake once again — only this time there were three brides. Joining Madonna for a rendition of the track were Britney Spears and Christina Aguilera, both of whom were trying to break out of their teen-idol boxes by proving how they were not, in fact, that innocent. Madonna decided to help both of them in that department, giving them mouth-on-mouth kisses — although the Britney one was steamier, and would be later teased in the video for their collab "Me Against The Music."

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