This category relaxes the criteria for entries slightly, accepting not only songs that are about gender-bending, but also songs from a perspective recognizably at odds with the vocalist's gender or which explore an alternate gender perspective on events in another song.
|21st Century Digital Girl||Groove Coverage||Major||7.2|
|Another Happy New Year||Spirit of the West||Major||2.4|
|As Girls Go||Suzanne Vega||Central||20.8|
|Dude (Looks Like A Lady)||Aerosmith||Central||16|
|Girl 4 A Day||Band Ohne Namen||Central||32|
|If I Were A Girl||Dave Days||Central||32|
|Lily The Pink||The Scaffold||Minor||8|
|Love Letter From China||Hayashibara Megumi, Yamaguchi Kappei||Minor||8|
|Moorlough Shore||Caroline Lavelle||Major||2.4|
|Sweet Polly Oliver||Central||16|
|The Lumberjack Song||Terry Jones, Michael Palin, Fred Tomlinson||Central||16|
|Truck Drivin' Song||Weird Al Yankovic||Central||16|
|Walk On The Wild Side||Lou Reed||Minor||16.9|
Each verse of the story is a vignette about a character who came to New York City, some of whom are transsexual prostitutes. "Taking a walk on the wild side" is a slang term for having a sexual experience with a cross-dresser.
While the concept of taking a walk on the wild side is central to this song, none of the individual characters take up more than one of the five verses, so none of them can really be called more than minor.
Because this is the first song I've ever seen where some lyrics sites indicate they were denied permission to display the lyrics, I've linked to two of the others, in case one gets taken down... but, seriously, what clueless executive thinks free lyrics can do anything but increase the chances that someone will want to buy a song?