32 Most Outrageous MTV VMAs Moments

Much like her oft-combative material, Fiona Apple’s words after receiving the Best New Artist Moonman were disorienting, yet poignant. After explaining that her speech would be different, and she’d say what she wanted to say because Maya Angelou would want it that way, she laid into pop idolatry. “This world is bullshit,” she said. “You shouldn’t model your life on what we think is cool, and what we’re wearing and what we’re saying and everything. Go with yourself.” And then she thanked her mom.

Besides maybe Kevin Federline, the biggest snake Britney Spears has ever encountered is the albino Burmese python she tangled with at the 2001 VMAs. Debuting the slinky Neptunes beat of “I’m a Slave 4 U,” Spears’ dance moves were taut and polished during this Amazonian performance even before Banana was placed, iconically, onto her shoulders. PETA was less than thrilled with the stunt, but at least pop star kept in touch with her reptillian co-star. As of two years ago, she reported that the python was alive and well.

Lady Gaga’s swift ascent to the forefront of pop music had one of its crowning moments when she garnered nine VMA nominations in her first eligible year. And she arrived at the broadcast ready to cement her status as a different kind of superstar, doubling down on the dark storyline of her nominated “Paparazzi” video with a surreal pop-art/art-pop performance. After some wacky masks and choreography, things took a turn when fame literally kills Gaga, and she closes the performance hanging from a noose, her face smeared in blood.

Few VMA pairings have been more inspired than Milton Berle and RuPaul, the most famous cross-dressers of the Forties and the Nineties, respectively, presenting a Viewer’s Choice Award to Aerosmith (not for “Dude Looks Like A Lady,” if you were wondering). But while it could have been comedy gold — Mr. Television himself in a three-piece suit standing at eye level with RuPaul’s push-up bra — their chemistry left something to be desired. Berle, rattled by the rowdy crowd, kept telling audience members “Shut up, will ya?” and stammered “He wasn’t supposed to say that!” when RuPaul adlibbed.

In the late Eighties, baby boomer rockers and Me Decade pop stars were displaying very different attitudes about musicians getting in bed with advertisers — and the last VMAs of the decade became an unlikely battleground. Pepsi sponsored the 1989 Viewer’s Choice Award, which went to Madonna’s “Like a Prayer,” a song premiered in a Pepsi ad. Video of the Year, however, went to “This Note’s for You,” a cantankerous comeback hit from Neil Young that humorously took aim at pop’s new wave of corporate synergy — a song, it should be said, contains the lines “Ain’t singing for Pepsi/Ain’t singin’ for Coke.” It was sweet revenge for Young, whose video was initially banned from MTV for its use of corporate trademarks.

Encased in over 40 pounds of thin-cut Argentinian beef, Lady Gaga cut a figure even more impressive than her dominant 13 nominations at the 2010 Video Music Awards. “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,” she later told Ellen DeGeneres regarding the symbolism of the gown. “And I am not a piece of meat.” Complete with beef-wrapped heels, hat, and purse, the outfit was assembled by L.A. designer Franc Fernandez with cuts from his family butcher, and reportedly had a sweet smell. Just before accepting the Video of the Year award for “Bad Romance,” she quipped, “I never thought I’d be asking Cher to hold my meat purse.” After a jerky-style preservation job, the dress was displayed at the Rock and Roll Hall of Fame.

In 2007 the Video Music Awards took over the Las Vegas casino the Palms, with not only performances on the venue’s main stage, but entire hotel suites given over to parties “hosted” by nominated artists. The train started going off the tracks from the opening close-up on Britney Spears’s hastily assembled wig, and got more chaotic from there. Kid Rock attacked Tommy Lee during Alicia Keys’s performance in an incident that caused Jamie Foxx to quip about “white-on-white crime.” West got upset that his performance was in a suite and not on the main stage and reportedly claimed he would “never return to MTV.” Mastodon guitarist Brent Hinds got into a post-show fight that resulted in a concussion, brain hemorrhaging and vertigo. The next year’s ceremony returned to the cozier confines of a Los Angeles studio lot — where West closed the show.

Well, or lack thereof…

A Best Director win for R.E.M.’s “Everybody Hurts” didn’t sit too well with the Beastie Boys’ Adam “MCA” Yauch — or at least his lederhosen-loving alter ego Nathanial Hornblower. As Stipe accepted the award, MCA stormed the stage, grabbing the mic in defense of director Spike Jonze, who directed the group’s video for “Sabotage.” “This is an outrage, because Spike is the director that has just — I’m from Switzerland, OK? Let me just tell everyone that,” MCA began in heavily accented speech. Things got a bit less coherent from there, with Yauch calling R.E.M.’s win a “farce” and saying he “had the ideas for Star Wars and everything.” Stipe quipped after the show: “At first I thought it was Bono.”

“Oh, sorry, my tit’s out?” Miley Cyrus asked coyly. It was only a matter of time before the “Free the Nipple” activist suffered a lack-of-wardrobe malfunction sometime during the 2015 VMAs. The camera tried to stop it — it cut away a few times — but it came in like a wrecking ball.

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.

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.

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.

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.

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.”

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.

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.

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.

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.

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.”

“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.

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.

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?”

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.

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.

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.

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.”