David Bowie
David Bowie (pictured above) continually challenged stereotypical expressions of masculinity through his gender non-conformist style and music. His unconventional embodiment of a sort of maleness and femaleness tested what the mainstream public associated with a virile, cisgender man.
Prince
Pop and R&B Icon, Prince (pictured above), "inlaid his albums with brazen pansexuality and gender norm coquetry. Years before the leaders of the gay and lesbian community began to embrace a more nuanced, less binary notion of queerness and decades before transgender and genderqueer politics became mainstream topics of interest, Prince presented a living case study in the glorious freedom a world without stringent labels might offer" (Cauterruci 2016, Slate writer). “I’m not a woman. I’m not a man. I’m something that you’ll never understand,” Prince sang on 1984’s “I Would Die 4 U.” He was right, few could claim to fully grasp Prince’s easy embodiment of both maleness and femaleness.
Annie Lennox
Annie Lennox challenged the aggressive promotion of hyper-feminization of female artists by embracing androgyny. She wore suits and close cropped haircuts (stereotypically male presentations) to present an image of women that went against the normative ideals of femininity.
Grace Jones
Grace Jones (pictured above) is iconic for her androgynous style and gender play. Jones says that even as a young child she possessed a certain masculinity that she eventually began to explore when she left her home in Jamaica to live in the United States. It was in the 1970's that she met her former partner, photographer, Jean-Paul Goude, who was captivated by Jones and became her creative director. Goude amplified Jones' masculinity by photographing her in suits with close cropped, flat top hairstyles, and makeup that accencuated her masculine feautures, which became the singer's signature look and propelled her to icon status as a symbol of androgyny.