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

Mar. 15, 2025

Taylor Swift with Joey Fatone, Lance Bass and Justin Timberlake of *NSYNC.Photo:TIMOTHY A. CLARY/AFP via Getty

TIMOTHY A. CLARY/AFP via Getty

FromMadonnakissing bothBritney SpearsandChristina Aguilerawhile performing “Like a Virgin” in 2003 toBeyoncérevealing she was expecting her first child in 2011 toTaylor Swiftbeing just as excited as the rest of us that*NSYNCwas together in the same room in 2023, over the four decades of VMAs history, viewers have caught someextremelymemorable moments.

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

01of 19The Most Nostalgia-InducingLance Bass, Joey Fatone, JC Chasez, Chris Kirkpatrick and Justin Timberlake.Kevin Mazur/GettyIn 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 toJustin Timberlake,Joey Fatone,JC Chasez,Lance BassandChris Kirkpatrickstanding 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!”

01of 19

The Most Nostalgia-Inducing

Lance Bass, Joey Fatone, JC Chasez, Chris Kirkpatrick and Justin Timberlake.Kevin Mazur/Getty

Kevin Mazur/Getty

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 toJustin Timberlake,Joey Fatone,JC Chasez,Lance BassandChris Kirkpatrickstanding 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!”

02of 19The SexiestJulie Jacobson/AP; Kevin Kane/WireImageNo 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.

02of 19

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

03of 19

The Happiest

Jeff Kravitz/Filmmagic

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.

04of 19The ShadiestKevin Winter/GettyFifth Harmonybegan 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 representCamila Cabello, wholeft Fifth Harmonyin 2016.

04of 19

The Shadiest

Kevin Winter/Getty

Fifth Harmonybegan 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 representCamila Cabello, wholeft Fifth Harmonyin 2016.

05of 19The RudestJason DeCrow/APKaty Perrysaid it best when she comparedKanye West’s2009 antics to steppingon a kitten. To recap:West famously ran up on stageto stach the microphone from a shockedTaylor Swift, who’d just beat outBeyoncéfor 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 declaredto a shocked audience.At the 2015 ceremony, the two seemed totemporarilybury the hatchet when Swift presented West with the 2015 Video Vanguard Award. (Alas, the detente was short-lived.)

05of 19

The Rudest

Jason DeCrow/AP

Katy Perrysaid it best when she comparedKanye West’s2009 antics to steppingon a kitten. To recap:West famously ran up on stageto stach the microphone from a shockedTaylor Swift, who’d just beat outBeyoncéfor 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 declaredto a shocked audience.

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

06of 19

The Raunchiest

07of 19The Naked-estDavid Drapkin/GettyWell, a lot of people have been pretty naked at the VMAs. But none did it more memorably thanLil' Kim, who wore a one-shoulder look that featured only a pastie on her left breast, causing co-presenterDiana Rossto give Lil' Kim’s decorated chest a joking jiggle as they hit the stage together.

07of 19

The Naked-est

David Drapkin/Getty

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

08of 19

The Feud-iest

Christopher Polk/Getty

09of 19The CringiestMichael Loccisano/GettyAt the 2016 awards,DrakepresentedRihanna, 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.

09of 19

The Cringiest

Michael Loccisano/Getty

At the 2016 awards,DrakepresentedRihanna, 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.

10of 19

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.

11of 19

The Goriest

How could we forgetLady 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.

12of 19The QuickestJeff Kravitz/FilmmagicIt 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.

12of 19

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.

13of 19

The Most Prestigious…?

Kevin Mazur/WireImage

From there, the “Billie Jean” singer gave an an acceptance speech for the very imaginary “artist of the millennium” award.

14of 19

The Strangest

15of 19The Most Marshall MathersFrank Micelotta/GettyWill the real Slim Shady please stand up?Eminembrought 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.

15of 19

The Most Marshall Mathers

Frank Micelotta/Getty

Will the real Slim Shady please stand up?Eminembrought 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.

16of 19The SultriestKevin Kane/WireImageShe’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 snakeand even declaring thatshewas the snaketwo 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.

16of 19

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 snakeand even declaring thatshewas the snaketwo 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.

17of 19

The Most Trailblazing

Madonna performing at the 1984 VMAs.Frank Micelotta/Getty

“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 onThe Tonight Showin 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, andLike a Virginwould become her first number one album.

18of 19The Prince-iestKevork Djansezian/AP/ShutterstockIn 1991,Princeperformed 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 factsheer fabric covering the artist’s rear end.

18of 19

The Prince-iest

Kevork Djansezian/AP/Shutterstock

In 1991,Princeperformed 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 factsheer fabric covering the artist’s rear end.

19of 19The Most Self Aware-istFrank Micelotta/ImageDirectNot 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 helpedturn the cornerin his acting career. Hermandied on July 30, 2023at 70 years old.

19of 19

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 helpedturn the cornerin his acting career. Hermandied on July 30, 2023at 70 years old.

source: people.com