There is no more bashful yet blatant love letter than the mix tape. No matter how the technology has changed -- call it a mix CD or an iMix, if you must -- the heart of it has stayed the same. At their best, they are carefully curated, obsessively arranged, and imbued with a thousand deeper meanings, each song carrying a secret message to the listener.
Our collection of gender-bending songs is as much a tribute to the artists who donned skirts instead of shitkickers as it is a gleefully raised middle finger to every driver cruising Main Street who had to rethink singing along when he finally clued in to the deliberately ambiguous pronouns.
To download these valentines to drag queens, androgynes, and girls who want boys who like boys to be girls, as Blur put it, go to iTunes.
1. Lou Reed, Walk on the Wild Side (1972)
Dressed in drugs, backroom fellatio, and prostitution, gender-bending left its gritty underground nest, hit the streets, and forced itself into the ears of millions in this thinly veiled bio of Warhol muses, including trans ladies Holly Woodlawn and Candy Darling. A trailblazing trans classic.
2. Hedwig and the Angry Inch, Wig in a Box," from Hedwig And the Angry Inch (2001)
Belting out rousing tracks like this, John Cameron Mitchell rescued us from Rocky Horror fatigue with his Golden Globe-nominated portrayal of a broken trans glam-punk with a weakness for vermouth, Bowie, and dickhead boyfriends. Wig is pure trailer-trash rock with a heart of gold.
3. Aerosmith, Dude (Looks Like a Lady) (1987)
"Never judge a book by its cover," Steven Tyler warns, skipping over exactly how anyone would be able to tell a transvestite bombshell from your average dude in a hair metal band. Of course he also pants, "Do me, do me, do me!"
4. Bitch and Animal, Best Cock on the Block (2001)
In praise of dicks that stay eternally hard and come in a variety sizes, shapes, and colors for every possible pleasure-providing occasion, Bitch and Animal promise the best cock on the block is like chick bait -- one bite and theyre hooked.
5. James, Laid (1993)
The sweet acoustic arrangement barely bothers to hide the song's sexual obsession with an insatiable girlfriend whose falsetto mocks, "Oh, you think you're so pretty." (He is.) The song's plea to "dress me up in women's clothes, mess around with gender roles" is borne out in the music video, where the band wears wispy, gorgeous frocks.
6. Cyndi Lauper, Ballad of Cleo and Joe (1996)
From her flagrantly queer album, Sisters of Avalon, this infectious club-thumper depicts a drag queens complicated double life. Set to a backdrop of operatic vocals, distorted accordion, and dizzying world beats, its the anthem for any dance-obsessed trans artiste.
7. The Killers, Somebody Told Me (2004)
The retrosexual breakout song from a band that looked and sounded like every queer '80s group thrown in a blender hit close to home: Somebody told me you had a boyfriend who looked like a girlfriend that I had. But they shrugged off the finer details of anatomy, crooning, Its not confidential, Ive got potential.
8. The Kinks, Lola (1970)
This may be the first time a top 10 hit encouraged the embrace of a mixed-up, muddled-up, shook-up world, where your bar pickup walked like a woman but talked like a man. But instead of rejecting Lola after the reveal, the song seems set on reminding you it's possible to find a certain comfort in simply going with the flow.
1. David Bowie, Rebel Rebel (1974)
No rocker toyed with gender like Bowie, as much a songwriting chameleon as he was a maestro of outr stage antics. Diamond Dogss funky, flippant highpoint finds its androgynous hero(ine) baffling mum and leaving a messy, glittery sheen on the dance floor. And damn if it doesnt have one of the best opening guitar riffs ever.
2. Blur, Girls & Boys (1994)
With its irresistible industrial-strength synth hooks, youd never know -- and maybe wouldnt care -- that Blur intended their biggest hit to be a caustic pop postcard addressed to the faddish, party-going, pansexual youth of mid-90s Britain.
3. Garbage, Cherry Lips (Go Baby Go) (2001)
Dedicated to anyone who is willing to try and survive, this sunshine-laced, three-minute parade was inspired by trans memoirist JT Leroy. What a shame Leroy turned out to be a veil for non-trans writer Laura Albert.
4. Pet Shop Boys, Electricity (1996)
Foppish front man Neil Tenant proves hes the perfect impressionist as he takes on the role of a lippy, lip-synching club diva in this dark, warbling trip-hop number. Hes all attitude when he coos, Im an artist, honey, but, as he himself admits, hes fucked if the tape dont start.
5. King Missile, Detachable Penis (1992)
In the style of SoCal joke-jock-rock (think Cake), this catchy, almost spoken word narrative recounts the morning after of a confused dude who can't seem to find where he left his precious parts during a raucous party. He eventually locates it at a sidewalk sale on St. Mark's Place in New York City, but still resists his friends' suggestions to have it "permanently attached."
6. Suzanne Vega, As Girls Go (1992)
Initially curious whether her friend kept the date with the steel side of the knife to make her more girl than girls are, Vega eventually proclaims she doesnt care where in Genderville her ambiguous gal pal comes from.
7. Tim Curry, Sweet Transvestite, from The Rocky Horror Picture Show film soundtrack (1975)
The camp classic cues the grand entrance of Dr. Frank-N-Furter -- the sweet transvestite from Transsexual, Transylvania -- onto the screen and into the pitter-pattering hearts of diehard Picture Show fans for generations to come.
8. Antony and the Johnsons, For Today I Am a Boy (2005)
Antony Hegartys angelic vocals soar in this raw, haunting hymn about a boy longing to transition and find true happiness, but by the time the song reaches its gorgeous climax, it seems hes transcended gender completely.
Additional track commentary and selection by Jason Lamphier and Noah Michelson.