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.

11. Madonna kisses Britney and Christina, respectfully marries them both.


I’m the devoutest of Madonna devotees, but even I think the momentousness of her kiss with Britney Spears (and a PR-jilted Christina Aguilera) seemed more ridiculous than right. I get that Britney was a big pop star, but nothing about her is the rightful heiress to Madonna’s throne — and this number tried to prove the opposite. Still, it’s an unforgettable performance, and Missy Elliott’s vaudevillian contributions shouldn’t be understated. If Madonna had waited six years to perform this same act with Lady Gaga, her Madgesty’s power-anointing kiss would’ve felt more appropriate. Plus, Gaga would’ve worn a wedding dress made of cold cuts or something. Sigh.

10. Madonna destroys Aerosmith with the comeback quip of the year.


The year was 1994. Madonna and David Letterman butted heads on his talk show and made up at that year’s VMAs. But afterward is when the real magic happened: Aerosmith won Video of the Year honors for “Cryin’,” and a wisecracking Steven Tyler took to the VMA microphone and tossed out a veeeeery lewd joke about Madonna, who stood feet away. “Why does Madonna use these two fingers to masturbate?” he pondered, before answering, “Because they’re mine.” Madonna allowed the audience’s shocked laughter to subside before she stole the microphone and responded, “If I used your fingers, then it’s not masturbation. It’s sexual abuse.” YES. Moral: Don’t mess with Madonna or her masturbation habits.

9. Madonna wins Video of the Year for “Ray of Light,” 1998
Madonna has a trove of Moonmen to call her own, but she didn’t score a Video of the Year win until 1998 when “Ray of Light” won the rightful honor. Never forget how kickass Madonna looked with straight, dark hair. It’s so… ashtangi!

8. Madonna dreams of Dietrich with “Bye Bye Baby” in 1993


Madonna has often invoked Marilyn Monroe’s image, but true fans know she’s much closer in identity and attitude to Marlene Dietrich. With this cabaret-style, chair-straddling performance of “Bye Bye Baby” from ’93, she took a ride on the Shanghai Express to a killer cinematic throwback.

7. Madonna gives the Video Vanguard Award to her favorite “diva” George Michael

I love most moments involving Madonna and her backup dancers Niki Harris and Donna De Lory, but this one may be best. In 1989, Madonna presented George Michael with the coveted Video Vanguard Award (a trophy she picked up in 1986 from presenter Robert Palmer), and after some cheeky line-readings and puffs on a cigarette, she proclaimed — in what I’m assuming was her own contribution to the speech — “Ladies and gentlemen, the diva himself, George Michael!” OK. Perfect.

6. The queen toasts the king at the 2009 ceremony.


Two superstars were born in August of 1958, and the surviving one toasted her fallen comrade (and 1991 Oscars date!) during a tense, but loving speech at the 2009 VMAs. Janet Jackson followed up with an “Unforgettable”-style duet with Michael Jackson on “Scream,” but Madonna’s articulate somberness was an appropriate and cool opening. The idea of Madonna trying to get Michael Jackson to eat French Fries is pretty great.

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

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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.

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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.

The MTV VMA Awards air Sunday August 25 at 9pm Eastern. You can cast your vote in 15 categories including Video of the Year here.