# 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:** 1
**Author:** ![tr0psn4j](https://avatars.discourse-cdn.com/v4/letter/t/958977/32.png) [@tr0psn4j](https://boards.straightdope.com/u/tr0psn4j)\ **Post date:** [December 28, 2009, 4:57am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/1 "2009-12-28T04:57:44Z")
A friend had once given me an mp3 of a weird song. It was sung by a guy and it was about cross-dressing. I’d like to hear it again, but I’m not in talking terms with that guy and Google hasn’t really helped me. So name a few songs about cross-dressing. 🙂 ---
**Author:** ![running\_coach](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/running_coach/32/15836_2.png) [@running\_coach](https://boards.straightdope.com/u/running_coach)\ **Post date:** [December 28, 2009, 5:03am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/2 "2009-12-28T05:03:46Z")
[Walkin’ Round in Women’s Underwear.](http://www.youtube.com/watch?v=foybsDsn5hk) ---
**Author:** ![NDP](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ndp/32/55_2.png) [@NDP](https://boards.straightdope.com/u/NDP)\ **Post date:** [December 28, 2009, 5:06am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/3 "2009-12-28T05:06:09Z")
Cross-dressing is brought up (or heavily implied) in these songs: “Lola” by the Kinks “Arnold Layne” by Pink Floyd “Walk on the Wild Side” by Lou Reed ---
**Author:** ![MPB\_in\_Salt\_Lake](https://avatars.discourse-cdn.com/v4/letter/m/c0e974/32.png) [@MPB\_in\_Salt\_Lake](https://boards.straightdope.com/u/MPB_in_Salt_Lake)\ **Post date:** [December 28, 2009, 5:11am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/4 "2009-12-28T05:11:36Z")
Van Morrison’s “Madame George” ---
**Author:** ![Oregon\_sunshine](https://avatars.discourse-cdn.com/v4/letter/o/50afbb/32.png) [@Oregon\_sunshine](https://boards.straightdope.com/u/Oregon_sunshine)\ **Post date:** [December 28, 2009, 5:15am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/5 "2009-12-28T05:15:00Z")
I’m guessing it was “Walk on the Wild Side”… ---
**Author:** ![Horatio\_Hellpop](https://avatars.discourse-cdn.com/v4/letter/h/e5b9ba/32.png) [@Horatio\_Hellpop](https://boards.straightdope.com/u/Horatio_Hellpop)\ **Post date:** [December 28, 2009, 5:34am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/6 "2009-12-28T05:34:53Z")
“Jane Says” by Jane’s Addiction “Where’s the Dress” by Moe Bandy and Joe Stampley ---
**Author:** ![Tim\_R.Mortiss](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/tim_r.mortiss/32/142_2.png) [@Tim\_R.Mortiss](https://boards.straightdope.com/u/Tim_R.Mortiss)\ **Post date:** [December 28, 2009, 5:41am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/7 "2009-12-28T05:41:37Z")
Monty Python’s “The Lumberjack Song”? ---
**Author:** ![Leiko](https://avatars.discourse-cdn.com/v4/letter/l/c5a1d2/32.png) [@Leiko](https://boards.straightdope.com/u/Leiko)\ **Post date:** [December 28, 2009, 6:36am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/8 "2009-12-28T06:36:36Z")
Weird Al’s “Truck Driving Song”? Doesn’t Brad Paisley have a song about wearing lady’s clothes? ---
**Author:** ![Polycarp](https://avatars.discourse-cdn.com/v4/letter/p/82dd89/32.png) [@Polycarp](https://boards.straightdope.com/u/Polycarp)\ **Post date:** [December 28, 2009, 6:39am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/9 "2009-12-28T06:39:55Z")
“Lola” ---
**Author:** ![Hazle\_Weatherfield](https://avatars.discourse-cdn.com/v4/letter/h/e9bcb4/32.png) [@Hazle\_Weatherfield](https://boards.straightdope.com/u/Hazle_Weatherfield)\ **Post date:** [December 28, 2009, 8:11am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/10 "2009-12-28T08:11:14Z")
> [@Krokodil](#): > > “Jane Says” by Jane’s Addiction > “Where’s the Dress” by Moe Bandy and Joe Stampley Isn’t “Jane Says” about a heroin addict who used to be Farrell’s roommate? ---
**Author:** ![Rodgers01](https://avatars.discourse-cdn.com/v4/letter/r/b19c9b/32.png) [@Rodgers01](https://boards.straightdope.com/u/Rodgers01)\ **Post date:** [December 28, 2009, 8:18am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/11 "2009-12-28T08:18:17Z")
Might have been [Wig in a Box](http://www.youtube.com/watch?v=6kySwhkpY4I) from Hedwig and the Angry Inch? ---
**Author:** ![Horatio\_Hellpop](https://avatars.discourse-cdn.com/v4/letter/h/e5b9ba/32.png) [@Horatio\_Hellpop](https://boards.straightdope.com/u/Horatio_Hellpop)\ **Post date:** [December 28, 2009, 8:56am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/12 "2009-12-28T08:56:16Z")
> [@Hazle\_Weatherfield](#): > > Isn’t “Jane Says” about a heroin addict who used to be Farrell’s roommate? And a transvestite, yes. ---
**Author:** ![jjimm](https://avatars.discourse-cdn.com/v4/letter/j/ba8739/32.png) [@jjimm](https://boards.straightdope.com/u/jjimm)\ **Post date:** [December 28, 2009, 9:11am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/13 "2009-12-28T09:11:50Z")
> [@Krokodil](#): > > And a transvestite, yes. Nothing I’ve ever read about Jane Bainter indicates she has ever been a transvestite. [Washington Post article](http://www.davenavarro.de/jane_WA.htm) (reprint), [Wikipedia article](http://en.wikipedia.org/wiki/Jane_Says), [picture of Jane Bainter](http://www.davenavarro.de/Bio/Bio_Jane.jpeg) then, [picture of Jane Bainter](http://gravitatetowards.blogspot.com/) more recently. IIRC, the wig was worn due to her involvement in the LA club scene. ---
**Author:** ![Tangent](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/tangent/32/3098_2.png) [@Tangent](https://boards.straightdope.com/u/Tangent)\ **Post date:** [December 28, 2009, 10:07am UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/14 "2009-12-28T10:07:56Z")
Dude Looks Like a Lady - Aerosmith ---
**Author:** ![panache45](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/panache45/32/64_2.png) [@panache45](https://boards.straightdope.com/u/panache45)\ **Post date:** [December 28, 2009, 1:07pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/15 "2009-12-28T13:07:22Z")
_“I’m Wishing You a Drag Queen Christmas”_ and _“I Am What I Am”_ from la Cage aux Folles ---
**Author:** ![asterion](https://avatars.discourse-cdn.com/v4/letter/a/4da419/32.png) [@asterion](https://boards.straightdope.com/u/asterion)\ **Post date:** [December 28, 2009, 1:28pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/16 "2009-12-28T13:28:39Z")
Isn’t “I’m A Boy” by The Who about forced cross-dressing? ---
**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 28, 2009, 2:43pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/17 "2009-12-28T14:43:55Z")
“Out of the Wardrobe” by the Kinks–none of the ambiguity of “Lola” there! “Rosie” - Joan Armatrading “Woman or a Man?” - Richard Thompson ---
**Author:** ![Ichbin\_Dubist](https://avatars.discourse-cdn.com/v4/letter/i/51bf81/32.png) [@Ichbin\_Dubist](https://boards.straightdope.com/u/Ichbin_Dubist)\ **Post date:** [December 28, 2009, 2:59pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/18 "2009-12-28T14:59:17Z")
There’s “Queen of the BBQ” by 80s Austin punk band The Hickoids (“he looks much better in a dress than you”), which is pretty obscure but not too obscure to be on a MySpace page: [!!!](http://www.myspace.com/hickoids) ---
**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, 3:08pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/19 "2009-12-28T15:08:39Z")
These songs _mention_ cross-dressing or cross-dressers but may not, strictly speaking, be _about_ them: _King For a Day_ - Green Day _Nancy Boy_ - Placebo _Funky Cold Medina_ - Tone Loc _Get Back_ - The Beatles _Laid_ - James _Where I Come From_ - Alan Jackson _Rebel Rebel_ - David Bowie There are lots about women dressing as men to join the army: _Sweet Polly Oliver_ (English folk song) _The Cruel War_ - Peter, Paul & Mary (among others) ---
**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, 7:42pm UTC](https://boards.straightdope.com/t/songs-about-cross-dressing/522776/20 "2009-12-28T19:42:18Z")
> [@Really\_Not\_All\_That\_Bright](#): > > _Rebel Rebel_ - David Bowie “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 ([lyrics here](http://www.sing365.com/music/lyric.nsf/Rebel-Rebel-lyrics-David-Bowie/9A334021EA83F4ED482568A20026656F)). [Lady Stardust](http://www.sing365.com/music/lyric.nsf/Lady-Stardust-lyrics-David-Bowie/4CE13886A78B73CF482568A2001433B2) is another song toying with gender identity, but not explicitly about cross-dressing. I _thought_ Bowie’s [Queen Bitch](http://www.sing365.com/music/lyric.nsf/Queen-Bitch-lyrics-David-Bowie/5DCB746104F9276A482568A20016EAC0) was about cross-dressing, but reviewing the lyrics, I’m not sure. Is the “queen” who pushes “ahead of the dames” a drag queen, or just a pushy broad? When the singer says “I can do better that,” is he saying he could find a better lover than her, or he could dress better than her, or he could please her man better than her? I find it all very confusing. > [@](#): > > There are lots about women dressing as men to join the army: > _Sweet Polly Oliver_ (English folk song) > _The Cruel War_ - Peter, Paul & Mary (among others) Oh, Bowie’s [She’s Got Medals](http://www.sing365.com/music/lyric.nsf/She%27s-Got-Medals-lyrics-David-Bowie/B342262412C0CA31482568A2002A8D35)\* fits in that category. No ambiguity there, except for the part about picking up girls. Whatever do you suppose she did with them? - One of several obscure novelty songs he recorded before “Space Oddity.” [Next page](https://boards.straightdope.com/t/songs-about-cross-dressing/522776.md?page=2)