The 10 Greatest VMA Moments Ever

Here’s a fact: In under three decades, MTV’s Video Music Awards have given us more iconic, bizarre, meaningful, meaningless, and awesome moments than literally any other award ceremomy on television. We’ll see if this year’s ceremony can live up to all 28 others tonight on MTV, but first, let’s remember the best moments in the VMAs’ kickass, hard-rocking history.

10. Taylor Swift’s beautiful dark twisted fantasy with Kanye West

As I remember it, the most mystifying part of the Taylor Swift/Kanye West acceptance speech debacle was the staging. As Swift attempted to thank MTV and her fans while brandishing the Best Female Video trophy for “You Belong to Me” in 2009, West suddenly appeared to her right — at a perfect camera angle, in record time — and snarked, “Taylor, I’m really happy for you and I’ma let you finish, but Beyonce had one of the best videos of all time.” The moment seemed ridiculous, yet well-choreographed. Was it fixed? I think not, but any moment that provokes heated debate about Network-style ratings stunts deserves a spot on this list.

9. Pee Wee Herman gets the joke

It took one porno theater masturbation scandal to make Pee Wee Herman a cult hero, and thus, his post-arrest reemergence at the 1991 VMAs was received in a sensational roar by the captive audience. After he soaked in the adulation, he asked one of the great rhetorical questions of our time: “Heard any good jokes lately?” Cheeky, little man. Cheeky.

8. Britney Spears “does it again” for the first time.

Forget the “Gimme More” fiasco and even the “I’m a Slave 4 U” snake dance of ’01; Britney’s definitive VMA moment is her sudden stripdown at the 2000 VMAs during a colossal version of “Satisfaction”/”Oops… I Did It Again.” To see Spears rip off her bedazzled blazer and slacks to reveal what looked like nothing but body glitter was shocking and scandalous — even after you realized it was a flesh-toned bodysuit. At the very least, the performance was a welcome delight after the drudgery of watching the Wayans brothers’ abysmal hosting.

7. Bon Jovi strums up a new generation of MTV greatness

If you can spawn the genesis of an entire MTV series with just one performance, you’ve earned yourself a place in history. When Jon Bon Jovi and Richie Sambora strummed and trilled onstage without any electrical accompaniment, their stirring versions of “Livin’ on a Prayer” and “Wanted Dead Or Alive” inspired the birth of MTV Unplugged, arguably the network’s most respected institution. Eric Clapton, Tony Bennett, and Lauryn Hill owe massive thanks to the Slippery When Wet hunks for kickstarting the album series that afforded them major comeback opportunities.


6. Afeni Shakur and Voletta Wallace toast their sons’ legacies

I’ve said it before and I’ll say it again: There is no topping the ’99 VMAs. Part of the reason is the surprise, touching connection onstage between Afeni Shakur and Voletta Wallace, the mothers of slain rappers Tupac Shakur and Christopher “Notorious B.I.G.” Wallace. With the help of Will Smith, who introduced the women, Ms. Shakur and Ms. Wallace exhibited a  connection that transcended the evening’s silliness at the Metropolitan Opera House and underscored the meaning behind the network’s music. Plus, they presented the Best Rap Video award to Jay-Z. Unforgettable, yet quaint.

5. Lady Gaga’s rawest moment

If you didn’t cackle with glee at the sight of Lady Gaga’s meat dress, you and I have little in common. Though Ms. Germanotta wore several ensembles during the 2010 VMAs, her final one — the uncooked meat outfit she wore while accepting Video of the Year for “Bad Romance” — is what will forever exemplify the singer’s showstopping irreverence. And in case you forgot, Gaga handed off her meat purse to presenter Cher, who was dressed in the leather jacket and micro-leotard from the “If I Could Turn Back Time” video.

4. Diana Ross fondles Lil Kim

But back to the glorious ’99 VMAs: Rapper Lil Kim’s outrageous, breast-exposing ensemble raised more than a few eyebrows with viewers, but no one was more intrigued with her gall than surprise presenter Diana Ross, who hugged Kim onstage before patting the breast with her own hand. The groping was so unexpected that the audience burst with applause and laughter, and in a hilarious twist, the most shocked person in the room was Kim herself.

3. Madonna vamps it up with “Vogue”

Here’s my vote for the most artful, winking, decadent, and naughty performance in VMA history: For the ’90 ceremony, Madonna needed to perform “Vogue” in a way that both recalled its iconic video and stood on its own as a breakout performance. While wearing lavish Marie Antoinette regalia and scoffing at scores of her male dancers in tiny shorts, Madonna held court and turned “Vogue” into a royal reception. And she even flashed the audience her old-timey underwear for added flavor. Brilliant and so definitively Madonna.


2. Michael Jackson and Lisa Marie Presley intrigue and repulse the universe with a single kiss.

The primary purpose of award shows is mayhem, and nothing incited mass chaos and destruction like newlyweds Michael Jackson and Lisa Marie Presley’s fascinatingly awkward liplock at the ’94 VMAs. “Just think,” Michael Jackson purred at the captive audience before the kiss, “Nobody thought this [his relationship with Presley] would last.” Naturally, the courtship soon ended, but the memory of Michael’s kissy aggression and Lisa Marie’s barely contained discomfort is emblazoned in every responsible VMA lover’s mind.

1. Madonna shows you just how “Like a Virgin” she is.

To understand the true magic of the VMAs, you have to go back to the very first ceremony in ’84. A brazen young starlet named Madonna crawled down a giant wedding cake, cooed a ditty called “Like a Virgin,” and rolled around in a wedding dress as if the whole room were deflowering her. No moment better defines MTV’s blend of sensational programming, rock ’n’ roll attitude, and unapologetic rauchiness. And it also cemented Madonna — who remains the biggest award winner in the ceremony’s history — as the eternal empress of the Video Music Awards.