Chely Wright

Chely Wright is a Country Music singer. She is known primarily for her hit "Single White Female" and pretty much nothing else. Far after this hit, Wright was the subject of much controversy in the fandom for coming out as a lesbian. Keep in mind that country music is one of the most conservative genres...

Chely Wright provides examples of the following tropes:

Bi the Way: The addressee of the song Like Me: "Who's gonna end up holding your hand - a beautiful woman or a tall handsome man?"
Corrupt Corporate Executive: Her fan club posed as family or friends of military members to plant requests for "The Bumper of My SUV".
The Four Chords of Pop: The stanzas of One Night In Las Vegas start with the familiar I-V-vi-IV progression.
Have I Mentioned I Am Heterosexual Today? and Hilarious in Hindsight: Try watching the video for Single White Female with a straight face these days.
Hot Teacher: Played this in Max Keeble's Big Move
Lipstick Lesbian
Old Shame: In-universe, "Back of the Bottom Drawer" has the singer digging through some detritus from previous relationships. She is ashamed of said relationships, but still can't bring herself to throw it away.
One-Hit Wonder: "Single White Female" was her only major hit.
Posthumous Narration: Notes to the Coroner
Shiksa Goddess: Became the lesbian answer to this trope when she married LGBT activist, Lauren Blitzer, in a Jewish/Christian ceremony
Tomboy and Girly Girl: Heavenly Days: "Tennessee tomboy, feminine girl, takin' a ride on top of the world..."
The Un-Reveal: When it was announced that someone in country music was going to admit they were gay, it caused something of a stir (country fans being very conservative.) When it was revealed it was Chely Wright, the response quickly shifted to "Who?!"
Writer Revolt: Wright's record company apparently disliked the gloominess of one of her recent albums, and requested that she write "something positive and hopeful". And so she did.