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15 Most Unforgettable VMA Performances in Music History

15. 1999: Britney Spears & ‘N Sync — Baby One More Time/Tearin’ Up My Heart


This is one heck of a pop throw back. Right around the new millennium, Britney & ‘N Sync were tremendously popular pop acts. This memorable VMA pairing had them performing their most popular hits from that time.

14. 1989: Cher — Turn Back Time


I think more people might actually remember Cher’s outfit than her actual performance; either way, the big-voiced diva solidified herself in VMA history. And remember–it’s not “time”, it’s “towm”! Thanks, Jack:

13. 1997: Puff Daddy, Sting, Faith Evans, 112 — I’ll Be Missing You/Every Breath You Take


This performance was dedicated to Notorious B.I.G., who was gunned down earlier that year in a tragic drive-by shooting. Respects were also paid to Princess Diana, Tupac Shakur, Gianni Versace, and others that were lost around that time. Faith Evans was the wife of Biggie, but the two were separated when he died.

12. 1990: Madonna — Vogue


A Victorian-inspired performance which introduced mainstream pop culture to vogue-ing, a dance style that originated from LGBT people of color performing in Harlem ballrooms. It’s got a really interesting back story. If you’re interested, the acclaimed documentary Paris is Burning covers the subject, and is available to stream on Netflix-instant.

11. 2011: Lady Gaga (Jo Calderone) — You And I


Lady Gaga took some inspiration from drag culture and appeared as Jo Calderone to perform a wonderful rendition of “You And I,” beginning with a somber piano introduction and leading into a big dance number. Gaga would only answer interview questions as Jo while she was at the VMAs. Queen’s famous guitarist Brian May also made an appearance for a guitar solo. Our favorite moment was Justin Bieber’s look of utter confusion.

10. 1989: Bon Jovi — Livin’ On A Prayer/Wanted Dead Or Alive (Acoustic)


This is the performance that inspired MTV’s popular Unplugged series, where artists stripped down their sound to the basics.



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