Most Shocking MTV VMAs Moments: Britney Spears & Madonna’s Kiss, Kanye West & Taylor Swift and More
Madonna only had four minutes (more or less) to nail her VMAs performance.
And the pop icon made crushing her 2026 MTV Video Music Awards homecoming look easy, even though it had been nearly two decades since she last graced the MTV stage.
For the Sept. 27 awards ceremony held at the Peacock Theater, Madonna had a big top hat to fill, given that her last appearance in 2003 went down in history when she kissed Christina Aguilera and Britney Spears on stage.
And this time around, the “Like a Prayer” singer continued to bring the star power with a ton of celebrity cameos. In addition to performing “Bring Your Love” with Sabrina Carpenter, Madonna sang “Danceteria” with Charli xcx—both hits from her latest album Confessions II.
But they weren’t the only big names to make an appearance. Julia Garner, Seth Rogen, Sombr and Debi Mazar were also among the celebrities to take the stage.
It’s no surprise the quintessential New Yorker had the Los Angeles audience on their feet. In the room for Madonna’s show-stopping comeback were stars including the evening’s host Snoop Dogg, BLACKPINK‘s LISA and Taylor Swift, who was there to be awarded the inaugural Artist Director Honors.
And across 42 years of the beloved music celebration, the “Like a Virgin” singer’s impact stands on its own. Her 13 nominations this year—including for Video of the Year, Artist of the Year and Song of the Year—follow 19 wins since 1984, when she christened the first-ever VMA stage by popping out of a wedding dressed as a bride.
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Aside from winning Moon People for her unforgettable music videos like “Vogue” and “Express Yourself,” she was also named a Video Vanguard in 1986.
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Indeed, it’s set to be an electric evening all around, as Nirvana was named the 2026 Video Vanguard recipients. The rock legends—including the late Kurt Cobain, Krist Novoselic and Dave Grohl—also share a special relationship with MTV, where they debuted their video for 1991’s “Smells Like Teen Spirit.”
To relive all the moments that make the VMAs so note-worthy, read on.
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Kanye West, 2009
The rapper crashed the stage when Taylor Swift won Best Female Video because he thought Beyoncé “had one of the best videos of all time.” When Bey later won for Video of the Year, she asked T.Swift to join her on stage to have her moment.
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Michael Jackson & Lisa Marie Presley, 1994
Shortly after their wedding, the couple walked on stage holding hands as the audience cheered. After Jackson declared, “I’m very happy to be here and just think, nobody thought this would last,” the King of Pop and Elvis Presley‘s daughter shared a kiss and walked off.
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Beyoncé, 2011
The pop star announced she and Jay-Z were expecting their first child together when she cradled her baby bump on the red carpet and literally dropped her mic and rubbed her baby bump at the end of her performance of “Love On Top.”
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Madonna, 1984
The “Material Girl” famously sang “Like a Virgin” while rolling around the stage in a white wedding dress.
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Lady Gaga, 2010
Gaga made headlines when she sported the now-unforgettable meat dress by Franc Fernandez as the most awarded star of the night.
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Britney Spears & Madonna, 2003
To open the show, Britney, Madonna and Christina Aguilera joined together for a rendition of “Like a Virgin” and “Hollywood,” sealed with a headline-making kiss between the women.
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Diana Ross and Lil’ Kim, 1999
While presenting Best Hip-Hop Video, the legendary singer unexpectedly tapped Lil’ Kim‘s exposed left breast.
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Rage Against the Machine, 2000
Who could forget when Rage Against the Machine bassist Tim Commerford expressed his displeasure at the band losing an award to Limp Bizkit by storming the stage and scaling a display tower? Although his moment was short-lived on television—since the network cut to a commercial—in reality, Tim’s night was not since he was arrested and sentenced to a night in jail.
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Lil Mama, Jay-Z and Alicia Keys, 2009
Believe or not, the Kanye West–Taylor Swift incident was not the only impromptu onstage moment to happen during the 2009 show. After the now-infamous interruption, Lil Mama decided to unexpectedly join fellow New Yorkers Jay-Z and Alicia Keys during their duet of “Empire State of Mind.”
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Howard Stern, 1992
The Shock Jock lived up to his raunchy reputation when he was lowered onto the stage as a superhero named Fartman.
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Kurt Cobain vs. Axl Rose, 1992
The two were involved in one of the most famous rock feuds. At the 1992 VMAs, tensions ran high backstage, where Cobain’s wife Courtney Love, who also brought along then-newborn daughter Frances Bean, taunted Rose, prompting the Guns N’ Roses frontman to threaten to beat up Cobain if he didn’t shut his “bitch” up. Kurt then told Love, sarcastically, “Shut up, bitch!”
After he performed with his band Nirvana, the group’s drummer Dave Grohl kept saying “Hi, Axl!” into his mic.
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Fiona Apple, 1997
The songstress won the award for Best New Artist in a Video, but used her acceptance speech as an opportunity to speak out against Hollywood, telling viewers, “This world is bulls–t.”
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Britney Spears, 2001
The pop princess unforgettably took the stage for her performance of “I’m a Slave 4 U” with a snake draped over her shoulders.
Jeff Kravitz/FilmMagic; E!
Eminem vs. Moby, 2002
Amid an ongoing feud between Eminem and Moby, Triumph the Insult Comic Dog poked fun at their beef while roasting the latter artist to his face in the VMAs audience. Triumph then attempted to do the same to Eminem, who was not in the mood.
Eminem later took to the stage to accept the award for Best Male Video and said mid-speech, “That little Moby girl threw me out of my zone for a minute.”
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Britney Spears, 2007
The pop princess made her highly anticipated return to the VMA stage, though her performance of “Gimme More” was panned.
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Justin Bieber, 2011
The Biebs had his own snake moment when he brought a baby boa constrictor named Johnson to the show.
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Nicki Minaj vs. Miley Cyrus, 2015
While accepting the award for Best Hip-Hop Video for “Anaconda,” Nicki confronted Miley, who was hosting, over negative comments she had made about the rapper in a New York Times interview. She called the pop star a “bitch” and asked her, “What’s good?”
Kevin Winter/MTV1415/Getty Images For MTV
Kanye West, 2015
At the end of his lengthy Video Vanguard acceptance speech, the rapper unforgettably announced his plan to run for president in 2020.
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Drake & Rihanna, 2016
The rapper sparked headlines when he declared his love for the songstress while presenting her with the 2016 Video Vanguard Award, telling the audience, “She’s someone I’ve been in love with since I was 22-years-old.”
Chelsea Lauren/Shutterstock
Fifth Harmony, 2017
On the heels of Camila Cabello‘s exit, the girl group shocked the world when they opened their performance with the image of a fifth member falling off the stage.
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