Gender-Bending Moments in Music

Janelle Monáe, Prince and Ciara have all tested tradition.

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)
Lady Gaga - Lady Gaga is known to push the envelope and in 2011 she up and changed genders. Mother Monster attended the 2011 MTV Video Music Awards dressed as her fictional male alter-ego, Jo Calderone, from her "You and I" video. Gaga said Jo was created to help "shift the world's perspective on what's beautiful."(Photo: Kevin Winter/Getty Images)
Grace Jones - Long before Gaga broke out of the gender box, Grace Jones was spearheading the look. Her 1980 Warm Leatherette album cover, shot by boyfriend Jean Paul-Geode, debuted the fiercely androgynous look she became known for. (Photo: Courtesy Island Records)

Next Gallery

Where Are They Now: The Cast of In Living Color

13 Photos

10 / 11

Lady Gaga - Lady Gaga is known to push the envelope and in 2011 she up and changed genders. Mother Monster attended the 2011 MTV Video Music Awards dressed as her fictional male alter-ego, Jo Calderone, from her "You and I" video. Gaga said Jo was created to help "shift the world's perspective on what's beautiful."(Photo: Kevin Winter/Getty Images)

ADVERTISEMENT