Gender-Bending Moments in Music

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

Mariah Carey

In the midst of her beef with EminemMariah Carey dropped a song called "Obsessed" (in 2009) along with a video in which she played dual roles, as a diva dressed in glam gear and a stan presumably the rapper cloaked in a hooded sweatsuit and a beard.

(Photo: Courtesy Def Jam)

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