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|
Dollar Bill (Music) By: Tanglefoot
This song is based on a real-life bootlegger from Kingston, Ontario, Canada. One verse describes him cross-dressing as part of evading the law.
Note: The only copy of the lyrics I could find is on the band's official website, where they only let you link to the entire album rather than to individual songs.
|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|