11 Most Iconic VMAs Performances: From Britney’s Snake Shimmy to an Army of Slim Shadys (Videos)

Nirvana began with a banned song, Missy Elliott worked it and Lady Gaga popped off with “Paparazzi”

Britney Spears at the 2001 VMAs
Britney Spears performing at the 2001 MTV Video Music Awards on September 6, 2001. (Scott Gries/ImageDirect)

The Grammys might be more prestigious, but MTV’s Video Music Awards is the ceremony where rising music stars really cut their teeth and industry legends cut loose.

Ahead of this year’s show, which is being held Sunday, Aug. 28, here are some of the most iconic performances since Madonna scandalized critics with her stage-humping version of “Like a Virgin” at the very first VMAs in 1984.

11. Lil Nas X and Jack Harlow, “Industry Baby” and “Montero” (2021)


Just last year, Lil Nas X turned heads (and lit up the internet) with his fiery performance of “Industry Baby” and “Montero” with special guest Jack Harlow. Beginning with a marching band outfit, Lil Nas X shed his shirt (and later pants) on a set that transformed into a prison shower.

10. The Beastie Boys, “Sabotage” (1994)

We know now that MCA, Ad-Rock, and Mike D. were versatile as hell, but — check with your Gen X friends and relatives on this — minds were blown back in 1994 when a rotating stage revealed that the three emcees could crush it on guitar as well as rock the mic. Adam Horowitz proved he could keep it on and on with a lung-bursting “Whyyyyyyyyyy?” at the two-minute mark.

9. Prince, “Gett Off” (1991)

TV censors were (no doubt) losing it when The Purple One revealed his see-through, rear-view pants about two minutes in as he sings, “Let me show you baby, I’m a talented whore,” while near-naked dancers writhe suggestively around him.

8. Nirvana, “Rape Me/Lithium” (1992)

MTV had ordered the groundbreaking grunge trio Nirvana not to play the controversially titled “Rape Me,” so imagine the collective heart attacks when Kurt Cobain launched into that very song, live. After a few bars, he switched over to “Lithium,” but the band continued its anarchic antics, with Kurt climbing the speakers and Krist Novoselic lobbing his guitar into the air and managing to hit himself in the head in the process. The moshing audience, some of who climbed on stage the better to dive back into the crowd, added to one of the most chaotic VMAs ever.

7. Eminem, “The Real Slim Shady/The Way I Am” (2000)

The show starts outside with dozens of Eminem lookalikes as they troop behind the real Slim Shady into Radio City Music Hall, then shifts into his blistering, much-bleeped performance of “The Way I Am.”

6. Beyoncé, “Baby Boy/Crazy in Love” (2003)

It’s always epic when Beyoncé hits the stage and her VMA performances have grown increasingly more elaborate and artistic (including being “arrested” by riot police in 2006 for “Ring the Alarm,” and her stunning Lemonade medley in 2016). But, it’s hard to top the energy and excitement of the 2003 show, where she makes her entrance hanging upside down(!), with the crowd going absolutely wild. The performance crescendos when Jay-Z joins her on their monster hit “Crazy in Love.” The power couple were rumored to be dating at the time, but didn’t make their relationship official until the next VMAs in 2004. 

4. Madonna, Britney Spears, Christina Aguilera and Missy Elliott, “Like A Virgin/Hollywood” (2003)

Britney and Xtina both appear in bridal outfits to belt out “Like a Virgin,” before being joined by the original Material Girl herself singing “Hollywood” in an outfit that’s half groom, half circus master. Madonna shares open-mouth kisses with both (pearls were most definitely clutched) and then Missy Elliott takes it up another notch.

4. Lady Gaga, “Paparazzi” (2009)

Lady Gaga, VMAs 2009
Lady Gaga preforms “Paparazzi” at the VMAs 2009. (Getty Images)

Talk about your operatic performances: A masked Lady Gaga started off lying on the stage, then hits the piano with one high-booted foot on the keys, staggers away bleeding (well done, propmaster) and ends by being lifted into the rafters by one hand. Watch the whole performance here.

3. Missy Elliott, “Work It” Medley (2019)

Missy Elliott 2019 MTV Video Music Awards
Missy Elliott 2019 MTV Video Music Awards. (Mike Coppola/Getty Images for MTV)

Missy Elliott left it all on the floor with an out-of-this-world medley the night she was honored with the VMA Video Vanguard Award. The seven-minute set (which is not on YouTube but can be streamed on Vimeo), featured multiple sets including a huge space ship, several costume changes and literal wig-snatching as she ran through hits including “The Rain (Supa Dupa Fly),” and “Get Ur Freak On.” Bonus: An all-grown-up Allyson Stoner, the little girl from the “Work It” video, showed she could still bust a move.

2. Britney Spears, “I’m a Slave 4 U” (2001)

Britney at her peak shimmying on stage with a snake is probably the first image that comes to mind when you think “VMAs.” Besides that enormous yellow python named Banana, the performance also featured live tigers, which we later learned were being handled by Mahamayavi Bhagavan of “Tiger King” fame.

1. Madonna, “Vogue” (1990)

Pop’s reigning music queen raised eyebrows in 1984 with her “Like a Virgin” performance, but six years later she was all taste and class — well, mostly — in this exquisitely choreographed and only slightly naughty show-stopper. Madonna switched out the Hollywood glamour of the video for an homage to “Dangerous Liaisons,” and somehow it worked brilliantly.