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.

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