Britney Spears, MTV VMAs 2001
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Like summer's end, the 2014 MTV Video Music Awards are fast approaching. If the show's 30-year legacy is any indication, we're in for superstar collabs and elaborate sets come Sunday (Aug. 24). To celebrate the annual spectacular, we’ve picked the best performances in VMA history. Pop megastars including Michael Jackson, Madonna, Britney Spears and Lady Gaga made a strong showing on the tally – but who had the most showstopping moment of all? Read on to find out where they ranked, and relive all the jaw-dropping, headline-grabbing performances.

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15. Justin Timberlake Medley (2013)

The sheer breadth of Timberlake’s catalogue is easy to forget, so the singer made sure to remind us during his Video Vanguard performance at the 2013 VMAs. Justin took the stage for over 15 minutes and ran through almost every one of his biggest hits. The best part? A mini ‘N Sync reunion -- the first in a decade ­- when his former bandmates joined him on stage for a few ultra-memorable moments.

14. Madonna, "Like a Virgin" (1984)

Already a huge star when she took the stage, Madonna went supernova at the inaugural VMAs and set the bar for every artist in her wake. The imagery from that performance ­- the wedding dress, walking down the cake, writhing on the floor -­ became so iconic that Madonna herself repeated it with Britney Spears and Christina Aguilera during her also-memorable 2003 performance.

13. Diddy feat. Sting, Faith Evans & 112, "I'll Be Missing You” (1997)

As memorable as it is meaningful, this Diddy tribute to the Notorious B.I.G got plenty of big names to participate: Biggie’s widow, Faith Evans, R&B group 112 and Sting, who stopped by to contribute live vocals to The Police’s “Every Breath You Take” sample. It remains one of hip-hop’s more touching and tender moments.

12. Britney Spears, "Oops I Did It Again" (2000)

Spears has had many showstopping VMA moments over the years, but the pop princess’ 2000 performance remains one of her most iconic. After kicking things off with her cover of the Rolling Stones’ “(I Can’t Get No) Satisfaction,” Spears proceeded to strip down to a nude bikini top and hip-hugging pants, shake out her blonde hair and and dance her heart out, growing from a precocious little girl into a sexy, grown-ass woman right before our eyes.


11. Rihanna, “Disturbia”/ “Seven Nation Army” (2008)

Subtly sampling the beat from the White Stripes' "Seven Nation Army" with her own haunting pop, Rihanna kicked off the 2008 VMAs with "Disturbia." Naturally, an onslaught of "Thriller"-esque dance-zombies took the stage and rounded out the eerie gig.

10. Taylor Swift, “You Belong With Me” (2009)

Country gal Taylor Swift got a taste of the big city life at the 2009 VMAs, performing "You Belong With Me" on the uptown F train before emerging from the subway and climbing on top of a taxi. Swift was riding high from the innovative performance, until Kanye West proceeded to bring her down a peg later that night with his "I'm gonna let you finish..." rant.


9. Kanye West, "Runaway" (2010)

It was a performance that could only come from the mind of Yeezy. Alone on a black and white stage, West wore a vibrant red suit and played DJ before launching into his huge self-referential hit about toasting the douchebags and assholes. Ballerina dancers joined him onstage briefly, but then Yeezy was left alone to shine. Just how he likes it.

8. Beyonce, “Love on Top” (2011)

When Beyonce strutted on stage at the 2011 VMAs in her tux-inspired suit and belted out "I want you to feel the love growing inside of me," the internet was freshly alight with reports that she was pregnant following a glowing walk down the red carpet. Her energetic performance of "Love On Top" keyed into the news that she and Jay Z were expecting, but when she dropped the mic, unbuttoned her jacket, winked and rubbed her belly with a big smile, viewers everywhere were captivated.

7. Eminem, “The Real Slim Shady”/ “The Way I Am” (2000)

Performing amidst a sea of Eminem lookalikes, Marshall Mathers made his point loud and clear at the 2000 VMAs: He is and will always be the Real Slim Shady. In an image etched into our minds, Em led his the imitators through Radio City, later busting right into "The Way I Am."


6. Britney Spears, “I’m a Slave 4 U” (2001)

All sexy and grown-up, Britney busted out in a big way at the 2001 VMAs, channeling the sauna vibe of her "I'm A Slave 4 U" video with a jungle-themed performance. But the real star of the show was the albino python that she wore around her neck like little more than a sexy accessory.


5. Chris Brown & Rihanna, “Wall To Wall”/ “Umbrella”/ “Kiss Kiss” (2007)

The carnival-esque Charlie Chaplin routine to "Wall To Wall" that opened Chris Brown's nearly six minutes on stage performing at the 2007 VMAs was just the beginning. Soon he was leaping across the seven mini-stages in the audience. But things truly kicked into high gear when Rihanna, in a sexy black ensemble, joined him for an interlude of her hit "Umbrella." Lest he let her steal the show, he grooved into full-on classic Michael Jackson mode with "Billie Jean" inspired moves before breaking into his own "Kiss Kiss."

4. Lady Gaga, “Paparazzi” (2009)

In what may be Gaga's best awards show performance ever, Mother Monster riffed on her "Paparazzi" video with a treatment that was equally as epic. Instead of the video's paralyzing fall, Gaga takes one in the chest, dripping faux blood on stage and being strung up from the ceiling. Even for Gaga, the moment was gasp-worthy.


3. Bon Jovi, “Livin’ On a Prayer”/ “Wanted Dead or Alive” (1989)

In a performance largely credited with inspiring MTV's massively popular "Unplugged" series, Bon Jovi brought its hair pop-metal down to earth for a riveting acoustic jam session. Jon snapped and strummed along with Richie Sambora's double guitar, as the two brought down the house with two of the band's biggest hits, portrayed this time in a more modest light.


2. Madonna, “Vogue” (1990)

Talk about a cultural mashup: Madonna and her company of dancers, clad in 18th century Marie Antoinette garb, taught the world how to vogue, a performance style popularized in underground gay dance clubs of the '80s. Cue one incredibly animated pants-less dancer, and VMA magic is made.

1. Michael Jackson Medley (1995)

Michael Jackson proved, yet again, just why he was the King of Pop at the '95 show. Not only did he give MTV viewers a 15-minute medley of many of his biggest hits (including "Beat It," "Billie Jean," "Black or White," "The Way You Make Me Feel" and more); he did it with on-stage costume changes, moonwalking, Slash shredding on guitar, dance-fighting and enough crotch-grabbing for the whole of the '90s. Such was the awesome power of this spectacular MJ performance, which set the standard for today’s Video Vanguard performances.