The Wildest MTV VMAs Moments Ever, from Sexy Kisses to Surprise Reunions

Ahead of the show's 40th anniversary on Sept. 11, 2024, look back at these extremely memorable moments from Beyoncé, Taylor Swift, Madonna and more music superstars

This year's MTV Video Music Awards, airing live from the UBS Arena in Long Island, New York on Sept. 11, will mark the awards' 40th anniversary — and what a wild ride it's been.

From Madonna kissing both Britney Spears and Christina Aguilera while performing "Like a Virgin" in 2003 to Beyoncé revealing she was expecting her first child in 2011 to Taylor Swift being just as excited as the rest of us that *NSYNC was together in the same room in 2023, over the four decades of VMAs history, viewers have caught some extremely memorable moments.

Here, a look back on 19 of the show's most jaw-dropping moments, ahead of 2024's honors.

The Most Nostalgia-Inducing

In 2023, fans were shocked to see all five members of *NSYNC, which had disbanded nearly 20 years earlier, walk out together to present best pop video. The crowd in the Prudential Center in New Jersey — and, we assume, audiences at home — went wild. And when Taylor Swift joined them on stage to accept the award, she was just as excited as the rest of us.

"I'm not doing well pivoting from this to this," she said as she began her acceptance speech, gesturing to Justin Timberlake,Joey Fatone, JC Chasez, Lance Bass and Chris Kirkpatrick standing behind her.

"I had your dolls," she continued (Kirkpatrick corrected her: "Marionettes!"). "Like, are you doing something? What's going to happen now ... They're going to do something and I need to know what it is!"

The Sexiest

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, passing down the pop diva torch as only she could.

The Happiest

Oh, baby! 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 – 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." Oh, now we get it!

It was a full circle moment four years later when JAY-Z and daughter Blue Ivy came out to present her with the 2014 Video Vanguard Award.

"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!"

The Shadiest

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.

The Rudest

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 to stach the microphone from a shocked Taylor Swift, who'd just beat out Beyoncé for best female video. He then memorably gave his own 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 to a shocked audience.

At the 2015 ceremony, the two seemed to temporarily bury the hatchet when Swift presented West with the 2015 Video Vanguard Award. (Alas, the detente was short-lived.)

The Raunchiest

Miley Cyrus shocked viewers by stripping down to a nude bikini top and briefs and grinding, twerking and thrusting on fellow 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.

The Naked-est

Well, a lot of people have been pretty naked at the VMAs. But none did it more memorably than Lil' Kim, who wore a one-shoulder look that featured only a pastie on her left breast, causing co-presenter Diana Ross to give Lil' Kim's decorated chest a joking jiggle as they hit the stage together.

The Feud-iest

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 ... 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.

The Cringiest

At the 2016 awards, Drake presented Rihanna, with whom he reportedly had an on-and-off thing, 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!). Rihanna later thanked the rapper for his words in a lengthy Instagram post about the night, which didn't quite give anyone hope Drake would make it out of the friend zone: "Your speech was so touching and I love you for that!" she wrote.

The Most Tone-Deaf

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 of pancreatic cancer just a month before.

The Goriest

How could we forget Lady Gaga's "Paparazzi" performance at the 2009 awards? Storming the stage to perform "Poker Face" before shifting to "Paparazzi," the rising star sang about the price of fame while fake blood gushed from her abdomen.

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?"

The Quickest

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.

The Most Prestigious...?

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.

The Strangest

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.

The Most Marshall Mathers

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.

The Sultriest

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 2021, posting a photo of herself in a lime green snakeskin catsuit.

The Most Trailblazing

Madonna's "Like a Virgin" performance at the very first MTV VMAs in 1984 set the tone for the headline-making moments to come. It was still early in her career when she dressed as a bride to descend from a 17-ft. wedding cake, but the performance took a left turn when she lost a heel and decided to improvise.

"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!"

She pretended to masturbate and finished the song with her dress over her head, exposing her rear end, so it's no wonder her manager was "white" with anger after the performance, saying she ruined her career, as Madonna recalled to Leno.

Instead, the pivotal performance proved to be Madonna's breakout moment, and Like a Virgin would become her first number one album.

The Prince-iest

In 1991, Prince performed his hit "Get Off" in his usual sexy style, turning around to reveal he was in butt-framing 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.

The Most Self Aware-ist

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. Herman died on July 30, 2023 at 70 years old.

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