Inspired by @soph & honestly just writing this list fucked me up sos [listen here: ]
  1. Now and Then - Kenny Loggins
    i can talk about this song for 20 years i love it so much
  2. Master & A Hound - Gregory Alan Isakov
  3. Passage - Vienna Teng
    i listened to this song while writing this list & it takes all the air out of your lungs its so haunting pls listen
  4. Firewood - Regina Spektor
    honestly it takes literally just the first line of this song to fuck me up
  5. I Can't Make You Love Me - Bonnie Raitt
    oh mannnn is all i can say
  6. In A Week - Hozier
  7. Operator (That's Not The Way It Feels) - Jim Croce
    i cant even comment on the rest of these but they're all beautiful aNd sad and u should listen to them all but not all at once
  8. Maybe - Lily Kershaw
    wow literally these all just have such specific emotions attached to them BYE
  9. Happy - Marina and the Diamonds
  10. Everything That Dies - Matthew and the Atlas
  11. Time - Pink Floyd
  12. Suddenly - Swear and Shake
  13. The Motherlode - The Staves
  14. Go Home - Lucius
  15. Heal - Tom Odell
  16. Dust to Dust - The Civil Wars
  17. A Case of You - Joni Mitchell
  18. I Of the Storm - Of Monsters and Men
  19. Beau's All Night Radio Love Line - Joshua Kadison
  20. Once Upon Another Time - Sara Bareilles
  21. While My Guitar Gently Weeps - Martin Luther McCoy (originally by George Harrison)
  22. Masochist - Ingrid Michaelson