Madonna at the VMAS: Her 10 most iconic moments

Madonna at the VMAS: Her 10 most iconic moments
·6 min read

Visual components are part of what made Madonna the pop icon she is today, so it's hard to imagine where she would be if MTV didn't exist.

Madonna's music videos were masterpieces in and of themselves, often telling heartbreaking stories or showing off the hottest dance moves taking over the floors of nightclubs across the country and world.

Madonna is synonymous with both MTV and the MTV Video Music Awards — happening again this Sunday, Aug. 28.

Here, we take a look back and count down the 64-year-old's most iconic VMAs moments:

10) C'mon girls!

At the 1989 VMAs, Madonna didn't go for second best baby when she performed the hell out of her hit "Express Yourself." Later that ceremony, she snagged the Viewer's Choice Award for "Like A Prayer." The award was famously sponsored by Pepsi, who had cut ties with Madonna over the controversial nature of the same video she was winning for.

9) Bootylicious

2021 MTV Video Music Awards - Show (John Shearer/MTV VMAs 2021 / Getty Images for MTV/ViacomCBS)
2021 MTV Video Music Awards - Show (John Shearer/MTV VMAs 2021 / Getty Images for MTV/ViacomCBS)

In 2021, Madonna surprised the audience at the MTV Video Music Awards when she opened the evening with her derriere on display to celebrate the ceremony's 40th anniversary.

In a sleek leather look, the 63-year-old pop icon cooed, “And they said we wouldn’t last. But we’re still here, motherf------!”

8) Faster than the speeding light, she’s flying

The same year Madonna won her first ever video of the year Moonman, she gave a spiritual performance of "Shanti Ashtangi" and "Ray of Light."

1998 MTV Video Music Awards (Kevin.Mazur / WireImage)
1998 MTV Video Music Awards (Kevin.Mazur / WireImage)

Vocally more challenging than most of her repertoire up until then, she rarely performed "Ray of Light" live because of its impressive scale. While not perfect, this performance reminded her fans that yes, she can sing and yes, she can sing live. Lenny Kravitz also made a notable guest appearance on guitar.

7) 'Michael Jackson was a hero'

A few months after the death of Michael Jackson in 2009, Madonna opened that year's VMAS with a poignant speech about the late superstar.

"There is no question that Michael Jackson is one of the greatest talents the world has ever known," she said. "That his music had an extra layer of inexplicable magic that didn’t just make you want to dance but actually made you believe you could fly, dare to dream, be anything that you wanted to be. Because that is what heroes do and Michael Jackson was a hero."

2009 MTV Video Music Awards - Show (Christopher Polk / Getty Images)
2009 MTV Video Music Awards - Show (Christopher Polk / Getty Images)

Despite being born the same exact month, the two musical icons didn't spend much time together amid their personal lives or professional careers. She did share a sweet story of one night they went to dinner together, explaining it was here she saw his vulnerability, something rarely on display for the public to see at this stage in his embattled life.

"Later we went back to my house to watch a movie and sat on the couch like two kids, and somewhere in the middle of the movie, his hand snuck over and held mine," she shared. "It felt like he was looking for more of a friend than a romance, and I was happy to oblige. In that moment, he didn’t feel like a superstar. He felt like a human being."

6) Will the real Madonna please stand up?

What's a better way to introduce Madonna than with a bunch of Madonna impersonators? Thats exactly what happened at the 1999 VMAs when a medley of her hits played and a gaggle of drag queens donning her most iconic looks sashayed down the runway, before the Material Girl herself came out to to her latest single at the time "Beautiful Stranger."

1999 MTV Video Music Awards (Jeff Kravitz / FilmMagic, Inc)
1999 MTV Video Music Awards (Jeff Kravitz / FilmMagic, Inc)

“All I have to say is it takes a real man to fill my shoes," she quipped on the microphone.

5) 'Like a Virgin'

Promoting her second studio album, Madonna was still a relative newbie trying to make a name for herself at the 1984 VMAs. She must have wished on an extra lucky star because she achieved exactly what she set out to do, wowing audiences in the crowd and at home with her performance of "Like a Virgin," rolling around the floor in her wedding dress and gloves that became of a staple of her look, recreated by her legions of fans for decades.

4) Love and war

The 12th Annual MTV Video Music Awards (Kevin.Mazur / WireImage)
The 12th Annual MTV Video Music Awards (Kevin.Mazur / WireImage)

Not all of the most iconic moments happen onstage at the VMAs.

In our No. 4 spot, an awkward showdown between Madonna and Courtney Love was caught on camera backstage when Madonna was being interviewed. Outspoken Love decided to crash the live shot by throwing things at the stage from below. She got her wish and got to join the sit-down, where the two musical icons traded barbs between each other, reading each other to fifth. Luckily for us, the awkward encounter has been memorialized on YouTube.

3) Don't mess with mama

When Madonna presented Aerosmith with the award for Video of the Year in 1994, Tyler made a joke at Madonna's expense and like the pro she is, she jabbed back with a barb that left the audience speechless. It's a lesser-known moment, maybe because it might have actually been edited out from the live broadcast.

1994 MTV Video Music Awards (Jeff Kravitz / FilmMagic)
1994 MTV Video Music Awards (Jeff Kravitz / FilmMagic)

"Why does Madonna use these two fingers to masturbate?" Tyler asked, before answering, "Because they're mine."

Madonna let the audience laugh at his cringey comment, before she took back the microphone with the response, "If I used your fingers, then it's not masturbation. It's sexual abuse."

Moral of this story: don't mess with Madge!

2) Is three a crowd?

Nineteen years after she first performed "Like a Virgin" on the VMAs stage, Madonna returned for another performance in 2003, but this time she had pop princess backup: Britney Spears and Christina Aguilera.

Britney Spears, Madonna, and Christina Aguilera (Scott Gries / Getty Images)
Britney Spears, Madonna, and Christina Aguilera (Scott Gries / Getty Images)

With Britney and Christina dressed in bridal couture, and Madonna in an all-black catsuit dressed like the groom, the trio ended their wedding themed-performance with a make-out session that sent waves through the music industry the next day. It became a career-defining moment for all three of them, so much so that Madonna and Britney recreated the kiss at Britney's wedding earlier this year.

1) Strike a pose!

In the No. 1 spot on our list is not controversy or crudeness, but the sheer creative genius when it came to the staging of her hit "Vogue" at the 1990 VMAs.

Portraying a sort of Marie Antoinette-inspired queen of the French Revolution, Madonna galloped around the stage in a powdered wig, enormous pannier skirt and frills, frills and more frills. With her dancers dressed as the attendees in her harem, the Queen of Pop was on her throne as she vogued her way through what would be regarded by fans and critics alike as one of the best performances ever in her storied career.