I grew up on the edge 70s glam, right through its 80s incarnation as hair metal, and then 90s acceptance of gender play. Bowie, New York Dolls; Poison and Motley Crue's eyeliner misogyny; and Kurt Cobain showing up on Headbangers Ball in a full ball gown. There are tons of examples of male artists finding ways to play with gender roles, but very few of women. Female artists, to have any chance at mainstream success, are stuck with the dichotomy of playing the sexy vixen, or the good, innocent virgin.
The recent popularity of artists like Janelle Monae and La Roux's Elly Jackson provided some much needed androgyny that didn't play to some male fantasy. (Yeah, Madonna wore a suit in "Express Yourself" but with a hefty dose of self-awareness, and her co-opting of gay culture never sat right with me.)
In the 80s, Annie Lennox with her tailored suits and red buzz bordered on revolutionary. I always thought that this, though, was really Annie in drag. There's something almost grotesque in its cliched femininity:
Cher channeled another one-named icon for her video for the cover of Mark Cohn's "Walking in Memphis." (Chelvis?) Not exactly known for stepping outside her Cher-persona, I still had to include this because it's still a drag performance at the core, and her cover of the song is pretty damn amazing.
Patti Smith was one of the first performers I loved who played with gender is a most unselfconscious way. I have some legitimate complaints about Patti: the stories I've heard of her being not so nice to her female contemporaries, choosing male role models almost exclusively, and eschewing feminism altogether, but it'd hard to deny her power. On thing I've always respected is that when covered "Gloria," an old Van Morrison song from his Them days, she didn't bother to change the song's pronouns.
And Coco Rosie is probably one of the best (or one of the few) examples of mixing drag, art and pop.
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