
- Trust-Billy Bragg. Have never been able to figure out if this is sung from a girls or boys POV. Rape is never upbeat.
- I Love You, Creedence-Casiotone For The Painfully Alone. Song for the hipster lonely.
- Damage-David Sylvian. "I only want to be in love"
- $35-The Aluminum Group. What makes this one sad is it is a true story. Listen to the lyrics and I'll tell you the story relayed to me offline.
- Medicine Bottle-Red House Painters. "I drank so much tea I wrote my letter in Kanji"
- Mexican Wrestler-Jill Sobule. Guess you can't force love.
- Il Adore-Boy George. This placement was a toss up between this and Culture Club's Less Than Perfect. Still not 100% on my choice.
- Scorn Not His Simplicity-Sinead O'Connor
- Marie-Townes Van Zandt. Homeless people and miscarriages. Fun.
- Till The Heart Caves In-kd lang. Lost unrecorded Roy Orbison tune.
- Half-Life Duncan Sheik. Always thought this was a song about being in the closet. Take it as you see it.
- Your Next Lover-Lori McKenna. and it goes a bit rootsy, sorry.
- Would You Still Have Fallen-Holly Williams. Got me through my dad's death.
- New Favorite (Edit)-Alison Krauss
- Come Pick Me Up Ryan Adams. The last 2 are more angry than sad. And he says Fuck.
- Why Don't You See Me?-Concrete Blonde. My default breakup/unrequited love song.
Bonus Track: Make It Easy On Yourself-Jerry Butler. Before my second attempt at uploading I realized I have 3 minutes of space left so stuck this on. I remember a break up in 98 where I went out to Hunters for a rebound the next day. As my friend Paul drove my drunk ass home, i turned this up on the car radio and screamed this out the window till I cried.

