Entertainment Music The Wildest MTV VMAs Moments Ever Sure, Miley's twerking made our list, but don't forget about these moments from Oasis, Madonna, Beyoncé and more music stars! By Kate Hogan Kate Hogan Instagram Twitter Kate Hogan is Director of Digital Specials and Features at PEOPLE. In her 14 years at the brand, she has covered everything from pets and babies to style and Sexiest Man Alive, interviewing celebrities including Céline Dion, Carrie Underwood, Jennifer Hudson and Chris Evans. Currently, she oversees the creation of photo galleries that complement breaking news and major PEOPLE moments like The Beautiful Issue and 100 Reasons to Love America. She has offered expert celebrity commentary on Good Morning America and Access Hollywood. Before joining PEOPLE in 2008, Kate was an editorial assistant at Morris Visitor Publications. She graduated from the University of Wisconsin-Madison with a Bachelor's degree in journalism and mass communication and resides outside of Chicago with her husband and three kids. People Editorial Guidelines Updated on August 25, 2022 03:50 PM Share Tweet Pin Email Trending Videos 01 of 25 The Sexiest Julie Jacobson/AP; Kevin Kane/WireImage No one will ever forget the opening number of the 2003 VMAs, when Madonna brought Britney Spears and Christina Aguilera along to perform "Like a Virgin," then kissed them both. 02 of 25 The Rudest Jason DeCrow/AP Katy Perry said it best when she compared Kanye West's 2009 antics to stepping on a kitten. To recap: West famously ran up on stage, snatched the microphone from a shocked Taylor Swift, who'd just beat out Beyoncé for best female video, and took over the speech. "I'm really happy for you, I'm gonna let you finish, but Beyoncé had one of the best videos of all time," he declared as the speechless audience looked on. 03 of 25 The Kanye-ist Kevin Winter/Getty Seemingly burying the hatchet (at least temporarily), Swift presented West with the 2015 Video Vanguard Award. Of course, the 2009 incident was mentioned, but it was all in good fun, as Swift said that West has had "one of the greatest careers of all time!" West then gave a buzzy acceptance speech in which he sort of apologized to Swift, dropped some sweet anecdotes about his daughter North and admitted to smoking pot pre-show. Highlight of the night. 04 of 25 The Shadiest Kevin Winter/Getty Fifth Harmony began their performance of "Down" in 2017 with five people on the stage, but before the song truly kicked off, one member was thrown off stage. Fans quickly assumed the booted performer was meant to represent Camila Cabello, who left Fifth Harmony in 2016. 05 of 25 The Raunchiest Jeff Kravitz/Filmmagic Miley Cyrus shocked viewers by stripping down to a nude bikini top and briefs and grinding, twerking and thrusting on fellow (married) performer Robin Thicke at the 2013 show in one of the raciest performances in MTV history. "Madonna's done it. Britney's done it. Every VMA performance ... that's what you're looking for; you're wanting to make history," the starlet said afterward. 06 of 25 The Quickest Jeff Kravitz/Filmmagic It was good while it lasted! Fans went wild when the original members of Van Halen walked the VMAs stage to present an award in 1996, appearing together for the first time in more than 11 years. Unfortunately, the reunion was short-lived: the group nearly came to blows (over a hip-replacement joke, no less) backstage, ending the reunion before the night was over. 07 of 25 The Beyoncé-ist Michael Tran/FilmMagic Receiving the Video Vanguard Award in 2014, Queen Bey took full advantage of her time on stage, delivering a killer 15-minute set of her hits before her husband JAY-Z and daughter Blue Ivy came out to present her with her statuette. "Thank you. I have nothing to say, but I'm thrilled with so much gratitude. I just thank God for this moment. I love y'all so much," she tearfully told the crowd. "My beloved, I love you. My fans, I love you. MTV, I love you. Good night!" 08 of 25 The Nakediest David Drapkin/Getty Well, a lot of people have been pretty naked at the VMAs. But in 1999, Lil' Kim wore a one-shoulder look that featured only a pastie on her left breast, causing co-presenter Diana Ross to give Lil' Kim's uh, lil girl, a joking tap as they hit the stage together. 09 of 25 The Awkwardest Jeff Kravitz/Filmmagic In a moment that was just so uncomfortable, the King of Pop, Michael Jackson, and his new bride, Lisa Marie Presley (only child of rock 'n' roll king Elvis Presley) attempted to prove to the entire world how "real" their marriage was by making out on stage at the 1994 awards show. "Just think, nobody thought this would last," Jackson said before initiating the kiss. Two years later the couple called it quits. 10 of 25 The Strangest Jeff Kravitz/Filmmagic Was it something we said? Oasis frontman Liam Gallagher went on one of his bad-boy tirades during a performance at the 1996 show by swearing, wandering the stage and making lewd gestures during his brother Noel's guitar solo. He finished the song by tossing a beer on the stage and storming off. 11 of 25 The Feudiest Christopher Polk/Getty Drama was brewing between VMAs host Miley Cyrus and Nicki Minaj prior to the 2015 awards, after Cyrus called the rapper "not too kind" in an interview with the New York Times. Minaj retaliated while accepting the award for best hip-hop video, starting with, "Now, back to this b---- that had a lot to say about me the other day in the press." Within seconds, though, she was letting it all out: "Miley, what's good?!" Cyrus was quick to defend herself, implying her words had been manipulated by the Times. The Internet was torn on whether or not the drama was real. 12 of 25 The Bluntest Adam Nadel/AP While accepting her best new artist award in 1997, Fiona Apple decided to scrap the typical thank-you speech and use the opportunity to share her deep thoughts on life. "This world is bulls---," she said. "You shouldn't model your life about what you think that we think is cool or what we're wearing or what we're saying. Go with yourself." 13 of 25 The Cringiest Michael Loccisano/Getty At the 2016 awards, Drake presented sometimes-flame Rihanna with the Video Vanguard Award, delivering a moving speech in which he said, "She's someone I've been in love with since I was 22 years old. She's one of my best friends in the world. She's a living breathing legend in our industry." When handing RiRi her statuette, he went in for a kiss — but the pop star turned her cheek (ouch!). Twitter freaked out, though Rihanna later thanked the rapper for his words in a lengthy Instagram post about the night, saying, "Your speech was so touching and I love you for that!" 14 of 25 The Fanciest Frank Micelotta/ImageDirect/Getty Let them eat cake! Madonna took costuming to a whole other lavish level for her 1990 performance of dressing up in extravagant royal garb that included an enormous wig, pearls, a pannier, a plunging neckline, a corset, fan and over-the-top set with gilded decor. After all, nothing is fancier than channeling Marie Antoinette! 15 of 25 The Happiest Jeff Kravitz/Filmmagic There has never been a smile so big! After rocking out on stage to her song "Love on Top" at the 2011 show, Beyoncé unbuttoned her sparkly jacket and put her baby bump on display, signaling to the audience that, yes, she was indeed pregnant. JAY-Z beamed from the front row, Kanye West was pumped – it was a joyous occasion for all. If only people had paid more attention to how she introduced the song: "I want you to stand up on your feet," she said. "I want you to feel the love that's growing inside me." Ah, like a baby! 16 of 25 The Most Tone-Deaf Michael Loccisano/Getty Read the room! Before presenting Video of the Year at the 2018 awards, Madonna paid tribute to Aretha Franklin, in a moment critics called totally tone deaf. The singer said that, if not for Franklin, she would not be Madonna, and then proceeded to speak about herself rather than focusing on Franklin's legacy. People were upset with not only Madge, but MTV as well, for what they saw as a lack of a proper tribute to the legendary Franklin, who died on Aug. 16, 2018 of pancreatic cancer. 17 of 25 The Goriest Christopher Polk/Getty How could we forget Lady Gaga's "Paparazzi" performance at the 2009 awards? Seizing the stage to perform "Poker Face" before shifting to "Paparazzi," the rising star sang about the price of fame and fake blood even gushed out of her abdomen toward the end of the tune. After she theatrically collapsed, her backup dancers tied and hoisted her up on a rope, rising above the crowd. The audience was shocked – which is just what Gaga envisioned. "I wanted to say something about how the celebrity sort of has this inevitable demise that we love to watch," she later told MTV that year. "But are we killing them or are they killing themselves? And do they love the fame and need it but not really want it? And why, when the cameras are there, do they shy away? But if the cameras were there for someone else, would they be jealous?" 18 of 25 The Most Prestigious...? Kevin Mazur/WireImage Talk about a birthday gift! The 2002 MTV VMAs fell on Michael Jackson's 44th birthday, and Britney Spears was tasked with presenting the King of Pop with a celebratory cake and special statue. However, the moment became infamously awkward when the starlet described Jackson as "the artist of the millennium" in her introduction, and Jackson thought he won an award of the same name. From there, the "Billie Jean" singer gave an an acceptance speech for the very imaginary "artist of the millennium" award. 19 of 25 The Sultriest Kevin Kane/WireImage She's a snake 4 u! Britney Spears stole the show when she held a live python and performed her hit "I'm a Slave 4 U" with a live python wrapped around her neck at the 2001 awards. The star would go on to reference the iconic moment through the years, dancing with a stuffed snake and even declaring that she was the snake two decades later, possibly alluding to her controversial conservatorship battle. "I held a snake at the @VMAS one time but decided to go ahead 20 years later and become the motherf------ snake myself 🐍🐍🐍 !!!!" she wrote on Instagram in June, posting a photo of herself in a lime green snakeskin catsuit. 20 of 25 The Most Marshall Mathers Frank Micelotta/Getty Will the real Slim Shady please stand up? Eminem brought the shock when he performed "The Real Slim Shady" at the 2000 awards show, walking down a line of dozens of real-life lookalikes queued up on Sixth Avenue in New York City. As he rapped about originality and making a name for himself in the music industry, the squad of Slims marched into Radio City Music Hall, where the VMAs were held. 21 of 25 The Most Iconic Courtest Everett Collection She went there! Madonna set the spark for crazy moments to come when she performed "Like a Virgin" at the very first MTV VMAs in 1984. Dressed as a bride and descending from a 17-ft. wedding cake, the then-up and coming singer lost a heel as she sang – but improvised. "So I thought, 'Well, I'll just pretend I meant to do this,' and I dove on the floor and I rolled around," she told Jay Leno on The Tonight Show in 2012. "And, as I reached for the shoe, the dress went up. And the underpants were showing. I didn't mean to!" Pretending to masturbate before hopping up to dance around and ending the performance with her wedding dress over her head (and her rear end exposed) Madonna told Leno her manager was "white" with anger after the performance, saying she ruined her career. Instead, the pivotal performance proved to Madonna's breakout moment, and Like a Virgin would become her first number one album, according to Biography.com. 22 of 25 The Most Controversial Kevork Djansezian/AP/Shutterstock Co-hosting didn't go quite so smoothly for RuPaul and Milton Berle at the MTV VMAs in 1993. MTV reports that the two tiffed backstage before walking out together on stage, where the drag queen then made a dig about the comedian "wearing diapers." When it came time to present the viewer's choice award, Berle told the audience to "Shut up, let him/her read it," before a visibly ticked RuPaul did the honors. 23 of 25 The Prince-iest Kevork Djansezian/AP/Shutterstock In 1991, Prince performed his hit "Get Off" in his usual sexy style, turning around to reveal he was in assless chaps. Years later, however, the designer revealed the ensemble wasn't actually peek-a-boo: there was in fact sheer fabric covering the artist's rear end. 24 of 25 The Hard Rock-iest Dave Hogan/Getty Rage Against the Machine bassist Tim Commerford climbed the set in 2000 as J.Lo presented to Limp Bizkit. Crew members tried to get him down without luck as the structure began to shake. "What are we fighting for?!" Kid Rock asked Carson Daly as he interviewed the crowd about the moment. Commerford was arrested for disorderly conduct and spent one night in jail. 25 of 25 The Most Self Aware-ist Frank Micelotta/ImageDirect Not long after he was arrested at a Florida theater for indecent exposure, Pee-Wee Herman, a.k.a. Paul Reubens, surprised the crowd when he appeared on the VMAs stage in 1991 and asked, "Heard any good jokes lately?" The move won him back some fans and helped turn the corner in his acting career.