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32 Most Outrageous MTV VMAs Moments

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

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

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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.

[Editor’s Note: a version of this story was published August 2016]

From Rolling Stone US

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Lil Mama Crashes Jay Z and Alicia Keys (2009)

Natia “Lil Mama” Kirkland’s only major hit, “Lip Gloss,” was already two years in the rearview by the time of the 2009 VMAs. There’s a good chance MTV wouldn’t have even invited her if she wasn’t employed by the network as a judge on America’s Best Dance Crew. Kirkland got a little caught up in the moment and decided to be part of the show when Jay Z and Alicia Keys performed their chart-topping ode to the Big Apple, “Empire State of Mind.” As the song came to a close, Kirkland decided to show her pride as a native New Yorker and join the two superstars onstage, posing in a b-boy stance while a nonplussed Jay Z did his best not to acknowledge her.

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Michael Jackson Accepts Imaginary “Artist of the Millennium” Award (2002)

The 2002 VMAs happened to coincide with Michael Jackson’s 44th birthday, and the producers thought it would be a nice occasion for some torch-passing — in this case, with birthday wishes (and a cake!) presented by Britney Spears. But Jackson, while standing backstage, heard Spears refer to him as the “artist of the millennium,” which led to him thinking he’d won a newly minted award with the same name. (The gift, which looked like a trophy, if not one of MTV’s Moonmen, probably helped further confuse matters.) His sweet acceptance speech — which included thanks to David Blaine — confused the audience at first, but they eventually rolled with it enough to give him a screamy ovation.

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Van Halen’s Reunion Hits the Skids (1996)

Van Halen’s lead-singer trouble is one of rock’s greatest soap operas. A pivotal chapter played out right in front of the VMA viewing audience, when David Lee Roth appeared with the band for the first time in over a decade to promote a couple of not-very-classic new songs they recorded for a greatest hits package — remember “Me Wise Magic,” anyone? The frayed relationship between Diamond Dave and Eddie Van Halen was still in evidence on the VMA stage, and it would be another ten years before the two could finally put their differences aside to tour together again.

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Courtney Love Interrupts Madonna (1995)

During Kurt Loder’s post-show red carpet interviews for the 1995 broadcast, Madonna, settling into her distinguished elder stateswoman era, was having a lovely conversation when another ambitious blonde began tossing items from her makeup bag. Loder invited Courtney Love up, and a few minutes of very strange, legendary live television ensued.

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Nirvana’s Krist Novoselic Takes a Bass to the Face (1992)

As Nirvana ascended to superstardom, they quickly became more famous for destroying their instruments than any band since the Who. But one night, at the height of their fame, Krist Novoselic’s bass did more damage to him than vice versa. Kurt Cobain played the impish troublemaker at the 1992 VMA’s, taunting Axl Rose backstage and telling MTV he’d rather play a new song called “Rape Me” than one of the band’s hits. But once Nirvana took the stage for a powerful performance of “Lithium,” Novoselic unintentionally grabbed the spotlight by tossing his thunder broom in the air, and failing to catch it as it came crashing down on his forehead. “I always try to get good air — I bet I hit over 25 feet, easy!” Novoselic remembered on his blog. “But no matter how high it went, I was not on my game — the only time I’ve ever dropped it was then in front of 300 million people.”

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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.

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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.

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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.

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Miley Cyrus, Robin Thicke and the Twerk Seen ‘Round the World (2013)

Putting together the two most controversial pop stars of the year is pretty much Peak VMA, although the particular combination of the gleefully provocative Miley Cyrus and the then-loucher-by-the-minute Robin Thicke pressed a lot of buttons. Cyrus’s continued appropriation of “twerking,” the age difference between the gyrating Cyrus and the Beetlejuiced-up Thicke, the wandering vocal pitch of both, the set’s “porn parody of a high school talent show” feel and the abuse of a foam finger kept the music media scratching its head for weeks. The incident has remained so ingrained in some peoples’ minds that it’s already inspired one finger-wagging organization, the Parents Television Council, to ask MTV to keep the 2014 ceremony clean. The PTC counts Cyrus’s dad Billy Ray among its advisory board members, so you know they’re serious.

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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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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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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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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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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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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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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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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.”