# Songs About Cross-Dressing? **URL:** \ **Category:** Cafe Society\ **Created:** [December 28, 2009, 4:57am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776 "2009-12-28T04:57:44Z")\ **Posts on this page:** 20\ **Page:** 2
**Author:** ![Diogenes\_the\_Cynic](https://avatars.discourse-cdn.com/v4/letter/d/e99b99/32.png) [@Diogenes\_the\_Cynic](https://boards.straightdope.com/u/Diogenes_the_Cynic)\ **Post date:** [December 28, 2009, 7:50pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/21 "2009-12-28T19:50:55Z")
> [@TWDuke](#): > > “You’ve got your mother in a whirl / She’s not sure if you’re a boy or a girl”? I’m not sure it’s about cross-dressing per se, or androgyny, or just a “your folks don’t understand you” kind of thing There’s more than that. I think there are other hints like, “You tacky thing, you put them on,” and the repeated tag of “Rebel, rebel, how could they know?” I always kind of assumed this song was about a tranny. ---
**Author:** ![Zsofia](https://avatars.discourse-cdn.com/v4/letter/z/7bcc69/32.png) [@Zsofia](https://boards.straightdope.com/u/Zsofia)\ **Post date:** [December 28, 2009, 7:53pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/22 "2009-12-28T19:53:21Z")
“The Lapdance is Always Better When the Strippper is Crying”? It includes the memorable line, “It’s hard to hide a hard-on when you’re dressed like Minnie Pearl.” ---
**Author:** ![TWDuke](https://avatars.discourse-cdn.com/v4/letter/t/e495f1/32.png) [@TWDuke](https://boards.straightdope.com/u/TWDuke)\ **Post date:** [December 28, 2009, 7:56pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/23 "2009-12-28T19:56:20Z")
**Dio** , I interpreted those lines differently (e.g., “how could they know” how much the singer loves the tramp), but that makes a lot of sense. I guess a lot of Bowie’s early songs were at least arguably about cross-dressers (shocker!). ---
**Author:** ![Really\_Not\_All\_That\_Bright](https://avatars.discourse-cdn.com/v4/letter/r/e8c25b/32.png) [@Really\_Not\_All\_That\_Bright](https://boards.straightdope.com/u/Really_Not_All_That_Bright)\ **Post date:** [December 28, 2009, 7:59pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/24 "2009-12-28T19:59:11Z")
What **Dio** said. ---
**Author:** ![RealityChuck](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/realitychuck/32/195_2.png) [@RealityChuck](https://boards.straightdope.com/u/RealityChuck)\ **Post date:** [December 28, 2009, 9:10pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/25 "2009-12-28T21:10:42Z")
The Beatles “Ob-la-Di Ob-la-da,” final verse: “Desmond stays at home and does his pretty face and in the evening she’s a singer in the band.” ---
**Author:** ![Thudlow\_Boink](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/thudlow_boink/32/320_2.png) [@Thudlow\_Boink](https://boards.straightdope.com/u/Thudlow_Boink)\ **Post date:** [December 28, 2009, 11:59pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/26 "2009-12-28T23:59:19Z")
“Have You Seen Jackie?” by The Dukes of Stratosphear ---
**Author:** ![wunderkammer](https://avatars.discourse-cdn.com/v4/letter/w/ed8c4c/32.png) [@wunderkammer](https://boards.straightdope.com/u/wunderkammer)\ **Post date:** [December 29, 2009, 2:11am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/27 "2009-12-29T02:11:13Z")
[“Boys”](http://www.youtube.com/watch?v=wCuL9Z019KE) by Bauhaus? At the very least, it’s got a lot of of androgyny and makeup. ---
**Author:** ![Really\_Not\_All\_That\_Bright](https://avatars.discourse-cdn.com/v4/letter/r/e8c25b/32.png) [@Really\_Not\_All\_That\_Bright](https://boards.straightdope.com/u/Really_Not_All_That_Bright)\ **Post date:** [December 29, 2009, 3:11am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/28 "2009-12-29T03:11:29Z")
Well, in that case, just about every Orgy and Poison song gets in. ---
**Author:** ![TWDuke](https://avatars.discourse-cdn.com/v4/letter/t/e495f1/32.png) [@TWDuke](https://boards.straightdope.com/u/TWDuke)\ **Post date:** [December 29, 2009, 3:26am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/29 "2009-12-29T03:26:30Z")
Oh, yeah, naturally cross-dressing is brought up in a couple of songs from The Rocky Horror [Picture] Show: “Sweet Transvestite” and “Don’t Dream It.” ---
**Author:** ![Roderick\_Femm](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/roderick_femm/32/14875_2.png) [@Roderick\_Femm](https://boards.straightdope.com/u/Roderick_Femm)\ **Post date:** [December 29, 2009, 7:15am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/30 "2009-12-29T07:15:45Z")
There’s a song called “Bruce”, by John Wallowitch, one of those uber-sophisticated East Coast types. It pretends to be funny, but it’s really just vicious. “and who were those awful old trolls? They looked like a bus-and-truck Cage aux Folles” “Don’t emulate Nancy, or Jacquie, You’re acting just as I feared. … My heart has an ache, Bruce, For haute couture’s sake, Bruce, Shave off your beard!” Roddy ---
**Author:** ![Johnny\_Q](https://avatars.discourse-cdn.com/v4/letter/j/898d66/32.png) [@Johnny\_Q](https://boards.straightdope.com/u/Johnny_Q)\ **Post date:** [December 29, 2009, 7:42am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/31 "2009-12-29T07:42:39Z")
Androgynous-- The Replacements ---
**Author:** ![Equipoise](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/equipoise/32/151_2.png) [@Equipoise](https://boards.straightdope.com/u/Equipoise)\ **Post date:** [December 29, 2009, 9:33am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/32 "2009-12-29T09:33:07Z")
This may not quite fit, but, [The Handsome Cabin Boy](http://www.youtube.com/watch?v=sDn_3VysILs). ---
**Author:** ![Ponderoid](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ponderoid/32/19221_2.png) [@Ponderoid](https://boards.straightdope.com/u/Ponderoid)\ **Post date:** [December 29, 2009, 9:36am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/33 "2009-12-29T09:36:26Z")
> [@RealityChuck](#): > > The Beatles “Ob-la-Di Ob-la-da,” final verse: “Desmond stays at home and does his pretty face and in the evening she’s a singer in the band.” That’s a screw-up they decided to leave in after having done way too many takes of the song. I guess it still counts, though. 🙂 ---
**Author:** ![Cicero](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cicero/32/3594_2.png) [@Cicero](https://boards.straightdope.com/u/Cicero)\ **Post date:** [December 29, 2009, 9:50am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/34 "2009-12-29T09:50:21Z")
Mrs Brown You’ve Got a Lovely Daughter. ---
**Author:** ![gaffa](https://avatars.discourse-cdn.com/v4/letter/g/e68b1a/32.png) [@gaffa](https://boards.straightdope.com/u/gaffa)\ **Post date:** [December 29, 2009, 10:20pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/35 "2009-12-29T22:20:21Z")
On Todd Rundgren’s classic _A Wizard/A True Star_ - _You Don’t Have To Camp Around_: \* Save the satin undies, don’t pluck out your eyebrows\* He had [lots of fun with the song](http://www.youtube.com/watch?v=iCanZ-8d9NI), and how he dressed at the time, in his recent tour of the album. ---
**Author:** ![joyfool](https://avatars.discourse-cdn.com/v4/letter/j/df788c/32.png) [@joyfool](https://boards.straightdope.com/u/joyfool)\ **Post date:** [December 29, 2009, 11:53pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/36 "2009-12-29T23:53:27Z")
_Jesse Jane_ by Alice Cooper. ---
**Author:** ![outlierrn](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/outlierrn/32/3005_2.png) [@outlierrn](https://boards.straightdope.com/u/outlierrn)\ **Post date:** [December 30, 2009, 2:01am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/37 "2009-12-30T02:01:12Z")
> [@Biffy\_the\_Elephant\_Shrew](#): > > “Out of the Wardrobe” by the Kinks–none of the ambiguity of “Lola” there! Lola is ambigous? > **[Lola (song)](https://en.wikipedia.org/wiki/Lola_(song)#Inspiration_for_the_song)** > > "Lola" is a song by the English rock band the Kinks, written by frontman Ray Davies for their 1970 album Lola Versus Powerman and the Moneygoround, Part One. The song details a romantic encounter in a Soho bar between a young man and Lola, who is possibly a trans woman or cross-dresser. In the song, the narrator describes his confusion towards Lola, who "walked like a woman but talked like a man", yet he remains infatuated with her. > The song was released as a single in the United Kingdom o... ---
**Author:** ![lost4life](https://avatars.discourse-cdn.com/v4/letter/l/c4cdca/32.png) [@lost4life](https://boards.straightdope.com/u/lost4life)\ **Post date:** [December 30, 2009, 1:40pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/38 "2009-12-30T13:40:23Z")
_I Wanna Get In Your Pants_ by The Cramps. Lux sings about wanting to get into a girl’s pants…literally. ---
**Author:** ![Biffy\_the\_Elephant\_Shrew](https://avatars.discourse-cdn.com/v4/letter/b/e47c2d/32.png) [@Biffy\_the\_Elephant\_Shrew](https://boards.straightdope.com/u/Biffy_the_Elephant_Shrew)\ **Post date:** [December 30, 2009, 2:15pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/39 "2009-12-30T14:15:58Z")
> [@outlierrn](#): > > Lola is ambigous? Yes, quite artfully and intentionally so. The fact that it was “inspired” by a specific incident doesn’t have any bearing on that. The purpose of art is to improve on reality. ---
**Author:** ![Jonathan\_Chance](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/jonathan_chance/32/701_2.png) [@Jonathan\_Chance](https://boards.straightdope.com/u/Jonathan_Chance)\ **Post date:** [December 30, 2009, 2:44pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/40 "2009-12-30T14:44:04Z")
“Looked Like a Woman (But Dressed Like a Man)” by Cowboy Mouth The tender, sensitive story about a man meeting a cross dressing woman in a bar and going home with her. > [@](#): > > She had muscles and a crew cut > She had shoes like mine > She had a way with a pool cue > She had a pick up line [Previous page](https://boards.straightdope.com/t/songs-about-cross-dressing/522776.md?page=1) [Next page](https://boards.straightdope.com/t/songs-about-cross-dressing/522776.md?page=3)