If dedication to excellence in vagina-related music were a role-playing adventure, these would be the top players on my server.
Besides having made perhaps the most formidable contribution to make-out music since Marvin Gaye, Prince has celebrated more sexual exploration and diversity in music that any other mainstream artist, even Madonna. I award this for all the pleasure-positive songs he's written about G-spots, vibrators, women who masturbate, cunnilingus, fantasy, gender exploration, safe sex, you name it.
With her long-running interest in women and politics, it's no surprise that Ani Difranco has sung about a lot of vaginal topics. I award this for the only well-known song about menstruation (Blood in the Boardroom), a song about abortion that both pro-life and pro-choice people can identify with (Lost Woman Song), and many other songs about sexuality, relationships, gender, feminism, and varied experiences of womanhood.
The strong, angry, female point of view often present in her songs has made PJ Harvey something of an accidental feminist icon, but her dedication to pursuing artistic rather than political goals makes her lyrics all the more diverse and complex. I award this for all the themes of fertility, desire, sexuality, and gender in songs like Man-Size, The Letter, Dry, and all the rest.
Tori Amos is nearly a developmental stage for sensitive teenagers. For a lot of people, she's the singer who writes about taboos and defiance. I award this for giving her fans songs to sing about masturbation, rape, cunnilingus, desire, and independent sexuality.
This band may have been officially based on gospel rock fusion, but it's difficult to ignore their obsession with pregnancy, birth and babies. I award this for weird songs about reproduction, and excessive use of the words womb and spawn.