Gender-Bending Moments in Music

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  • Janet Jackson
  • Cassie
  • Tyler, the Creator
  • Lady Gaga
  • Graces Jones
  • Janelle Monáe
  • Prince
  • Eminem
  • Earl Sweatshirt
  • Mariah Carey
  • Ciara

Tyler, the Creator and L-Boy

Odd Future's Tyler, the Creator and L-Boy threw on tennis skirts and tank tops to impersonate Venus and Serena Williams. The spoof was filmed for their Loiter Squad comedy show and fooled onlookers who showed up believing the tennis stars were on hand.  

(Photo: Courtesy Tumblr via bassmotel)

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