5 Eddie Izzard
A jack-of-all-trades best known for his stand-up comedy, Eddie Izzard is one of the most versatile performers of the 21st century. And he is a man. A heterosexual man. An executive transvestite! It’s no wonder he landed the role of Mr. Kite in Julie Taymor’s “Across the Universe.” Performing “Being for the Benefit of Mr. Kite” is one of his musical credits, but his stand-up shows include several impromptu musical numbers, including fake opera, dinosaur church hymns, and musicals about chickens. Izzard made his grand self-identification as a transvestite during his first major stand-up show. Since then he has been a champion of LGBTQ awareness.
4 Alex Davis
If you’re looking for soulful guitar playing, you’ve come to the right place. L.A.-based musician Alex Davis spent his whole life dealing with gender issues, and was blessed with open-minded parents. His simple lyrics like “I’d cut your hair for you if I could do it well” are poignant and beautiful. His gender identity informs his music only insofar as anyone’s personal identity informs his or her music. In Davis’ “Oh Sugar” you can’t help but feel like you’re falling in love. His music shows that love is love no matter what physical body it hides in.
Not strictly transgender, the Brooklyn-based folk-rock trio Girlyman simply exist to make good music. They are prominent members of the LGBTQ world, and have a massive “Girlyfan” base. Instead of worrying about redefining gender labels, Girlyman simply exist without them. When asked, vocalist/guitarist Doris Muramatsu said “a Girlyman is whatever you want it to be – just someone who is nontraditional in some sort of way, or likes to play with gender roles, or isn’t afraid to have a sensitive side.”.
2 Chaz Bono (Ceremony)
Chaz Bono was born Chastity Sun Bono to supernova-famous parents Cher and Sunny Bono. Chaz had been outed as a lesbian in the mid ‘90s before self-identifying in 1995. Sunny didn’t take it too well (he was a California republican congressman after all). Chaz’s musical endeavor, Ceremony, had a less technologically driven sound, and featured Chaz on vocals, acoustic guitar, and percussion. In 2008, Chaz underwent the process of gender reassignment.
1 Laura Jane Grace (Against Me!)
The most recently famous gender-bending musician, front man of punk group Against Me!, Tom Gabel came out as transgender in May 2012 and changed her name legally to Laura Jane Grace. Grace had been inspired to come out after meeting a transgendered Against Me! fan. In an act of true musical solidarity, Grace is fully supported by her band mates (as well as her wife) and Against Me! will continue to perform with their kick-ass punk front-woman.