Madonna’s 11 Greatest VMA Moments



We’re less than two weeks away from the 2013 MTV Music Video Awards, and crazier yet we’re only four days away from Madonna‘s 55th birthday. The histories of the VMAs and Madonna are so intertwined that it’s impossible to think of one without the other, and both should be celebrated with equal exaltation. That brings us to today’s journey: Madonna’s 11 Best VMA Moments. Tighten your bustier and pump your Moonman in the air, MTV generation.

5. The only kind of Madonna tribute that matters: a drag one.
The 1999 VMAs ranks among the greatest award shows ever: At the Metropolitan Opera House, an operatic choir chanted Kid Rock‘s “Bawitdaba,” Prince introduced a performance by TLC, and Lauryn Hill walked off with Video of the Year for her stellar clip “Doo Wop (That Thing).” But better yet, Madonna — who presented Video of the Year with Sir Paul McCartney — won a Moonman for “Beautiful Stranger” and got to watch a dozen drag queens vamp in fabulously classic Madge costuming. After examining the gents in their over-the-top attire (My favorite is still the “Bedtime Story” queen with the floating birds surrounding him), Madonna stepped up to the mic and deadpanned, “All I have to say is it takes a real man to fill my shoes.”


4. Madonna successfully convinces you to “Express Yourself” at the ’89 ceremony.
One of Madonna’s greatest looks: that industrial-hard bustier paired with baggy men’s slacks. Hell yes. Madonna sold the hell out of “Express Yourself” at the ’89 ceremony, where she also accepted the Viewer’s Choice Award for “Like A Prayer.” Famously, that award was sponsored by Pepsi, the same company that cut her loose (with pay!) after she debuted her blasphemously hot video for “Like a Prayer.”


3. Madonna survives and conquers Courtney Love at the ’95 VMAs
This is one of Madonna’s funniest moments, and it just may be Kurt Loder‘s finest hour: As the MTV newsman interviewed Madonna about her upcoming ballad collection Something to Remember at the 1995 ceremony, Courtney Love interjected from the red carpet by throwing her compact at the confused Ciccone. After Loder invited Love up to chat, Madonna braced herself for their confrontation, but it wasn’t long before Madonna unleashed a deadly medley of perfect putdowns. The best line? After Courtney Love says she doesn’t want to leave the “hospital” of entertainment because of the “nice clothes and good money,” Madonna retorts, “And plenty of available drugs.” I mean, fire. That’s how it’s done. As in: It will never be done better.


2. “Like a Virgin” for the very first time.
Everything great about the MTV Video Music Awards stems from this: Madonna’s extreme, paralyzingly naughty, and hilarious performance from the 1984 ceremony. The budding superstar had a new album to sell, and she thought she’d do it by wearing a wedding dress, humping the floor, and staring at the camera like a horny wolf. It is still eye-popping television. It is still spellbinding to watch Madonna pretend not to know her dress has stopped covering her body. It’s the best. Except, of course, for…


1. “Vogue” starts a Revolution for Frenchy men.
“Vogue” remains the quintessential Madonna moment. It’s an amazing song, but the video (and her performance of the song at the VMAs) showcased her best assets: cheeky glamor, nervy sexuality, awareness of pop iconography, and her proud domination of gay minions. In her Marie Antoinette getup at the ’90 ceremony, Madonna hustled around that stage ordering boys in booty shorts to eat cake, and God, do they. So outrageous, so marvelously choreographed, so fun, and so a spectacle only Madonna could pull off. Maybe “Like A Virgin” was more instrumental in making the VMAs a music institution, but “Vogue” was a Madonna-specific triumph. Put your opera glasses down and applaud.


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