Paula Cole

One of the more prominent female singer-song writers who gained popularity during the 90s, Paula Cole is probably best known for the song "Where Have All the Cowboys Gone" and the song which would become the theme to Dawsons Creek. Her songs are musically lush, but tends towards lyrically bleak with a dark bent.

Born in Rockport, Massachusetts to Stephanie, a visual artist, and Jim Cole, a polka-playing entomologist. She has a sister named Irene. She lived in Rockport with her parents, where she attended elementary school. She was an active and popular student in middle school and high school, holding offices as class president and student council member. This would become important later.

Political with an overtly leftist bent (except on her Grammy winning second album, which largely avoids political tropes), many of Cole's songs deal explicitly with such topics as feminism, racism and discrimination, and more general themes of social justice. Your Mileage May Vary as to how well she pulls this off, with results ranging from impressive to Anvilicious (and this is if you are in general agreement with her politics).

Discography:
 * Harbinger (1994)
 * This Fire (1996)
 * Amen (1999)
 * Greatest Hits: Postcards from East Oceanside (2006)
 * Courage (2007)
 * Ithaca (2010)

She provides examples of:
 * All Men Are Perverts: Maybe not all, but certainly all sex-starved high school teachers.
 * Black Sheep Hit: "I Don't Wanna Wait," a.k.a. the Dawsons Creek theme song.
 * Chained to A Railway: Played deadly and heartbreakingly straight.
 * Class Representative: The (probably auto-biographical) protag of Bethlehem struggles with her identity as one of these.
 * Conspiracy Theorist: "Amen for NASA,The NSA / It's all a front anyway"
 * High School: Bethlehem
 * Inner City School: Latonya
 * Intercourse With You: Carmen, Feelin' Love, and most explicitly Chiaroscuro. Oh John is slightly less direct, but it is basically just a song listing off the places she and the titular man got it on.
 * Mayfly-December Romance: The theme of the video for "I Don't Wanna Wait", as she portrays an immortal who takes and loses a series of lovers as the centuries roll on.
 * The Nineties: Aside from being most closely associated with this decade (and not having done much of note in the decade since), Cole's song Amen invokes many of the cultural tropes and public figures of the decade.
 * Protest Song: Watch the Woman's Hands sounds like a 60s feminist protest song, but the snaky My Hero, Mr. President! plays this trope far straighter.
 * Rape As Drama: She Can't Feel Anything Anymore, probably.
 * Small Town Boredom: Bethlehem
 * Used to Be A Sweet Kid: Danny in She Can't Feel Anything Anymore, depending on your exact interpretation of the song.