Gender-Bending Moments in Music

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

Eminem

Eminem contested manufactured pop music with his song "The Real Slim Shady," and in addition to lyrically calling out Britney Spears, who was the reigning princess of pop at the time, he dressed up like her for the accompanying video.

(Photo: Courtesy Interscope Records)

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