5 Times Madonna Stole the Show at the MTV VMAs

A look back at the Queen of Pop's most memorable appearances at the Video Music Awards, in no particular order.

Madonna and the MTV Video Music Awards go way back. Since the award show’s inception, the Queen of Pop has racked up an impressive total of 20 Moonmen, including a 1986 Video Vanguard Award, making her the first female recipient in VMAs history.

In honor of Madonna’s birthday this week, we’re highlighting some of her most memorable VMAs moments, in no particular order.

  1. “Like a Virgin”

    Frank Micelotta/Getty Images

    This legendary performance during the inaugural VMAs saw the Queen of Pop improvise her way through a major wardrobe malfunction. When she emerged from a 17-foot wedding cake during the “Like a Virgin” set (sporting her iconic “Boy Toy” belt, of course), she lost a shoe, prompting her to roll to the floor and dive around to play it off as intentional.

    “So I thought, ’Well, I’ll just pretend I meant to do this,'” Madonna told Billboard in a special 1984 feature. “And, as I reached for the shoe, the dress went up. And the underpants were showing.”

    The rest, as they say, is history.


  2. “Ray of Light”

    Frank Micelotta/ImageDirect

    The 1998 VMAs were a clean sweep for Madonna, who took home six Moonmen out of her nine total nominations for the iconic “Ray of Light” music video.

    She also took the stage during the show, performing a visually stunning mashup of the Hindu-inspired number “Shanti/Ashtangi” and, of course, “Ray of Light” with a guest appearance from Lenny Kravitz.


  3. “Vogue”

    Frank Micelotta/ImageDirect

    In the early ’90s, the VMAs were still something of a novelty, with boundary-breaking artists like Madonna continuing to pave the way for new acts to come.

    Madonna stole the show with her rendition of “Vogue” at the 1990 VMAs, appearing onstage in a stunning floor-length Rococo gown. Her flair for the dramatic made the opera-like performance a memorable one.


  4. “Express Yourself”

    At the ’89 VMAs, Madonna brought down the house with a performance of her hit “Express Yourself.” The track won her three Moonmen that year—and lent itself perfectly to a sexy show, with the Queen of Pop singing, gyrating, and strutting her stuff onstage.

  5. “Like a Virgin,” round two

    Chris Polk/FilmMagic

    Last, but certainly not least, another “Like a Virgin” performance: Who could forget when Madonna kissed Britney Spears and Christina Aguilera at the 2003 VMAs?

    The trio performed the Queen of Pop’s classic hit 19 years after its debut—and the steamy same-sex smooches with Madonna’s two onstage brides, outfitted in white corsets, elevated the super-sexy track to a whole new level.

Tune in for the 2019 Video Music Awards live from the Prudential Center in Newark, NJ, on August 26 at 8/7c.

Brooklyn-based writer and editor. Probably drinking iced coffee or getting tattooed.