But in a good way. I think. I'm not including purely instrumental tracks because that's for another day.
  1. Space Oddity
    by David Bowie. It took me a while to realise just how sad this song is when I was a kid.
  2. Medicine
    by Daughter. Or basically anything by Daughter.
  3. About Today
    by The National. Also basically anything by The National.
  4. Tornado
    by Jónsi. I saw this on a fanmix for Never Let Me Go once and it's made me super sad ever since.
  5. Kettering
    by The Antlers. From maybe the most tragic album of all time.
  6. Creep
    by Radiohead. Obviously.
  7. Elephants
    by Rachael Yamagata. "If the elephants have past lives yet are destined to always remember, it's no wonder how they scream. Like you and I they must have their temper."
  8. Asleep
    by The Smiths. Another obvious choice.
  9. The House That Built Me
    by Miranda Lambert. Growing up sucks.
  10. Everybody's Waiting
    by Missy Higgins. Most of her songs.
  11. Bluebird of Happiness
    by Mojave 3. From my favourite movie, Paper Man.
  12. A Better Son/Daughter
    by Rilo Kiley. If I had an "anthem" this would be it.
  13. Landslide
    by Fleetwood Mac. I am only fucking human.
  14. This Bitter Earth/On the Nature of Daylight
    by Dinah Washington/Max Richter. Yes, devastating. Even just Max Richter's composition, as used in Shutter Island.
  15. Hallelujah
    by Jeff Buckley. Yes, I know this is Leonard Cohen's song, but Jeff Buckley's cover won me over. This has been played at too many funerals and on too many sad TV shows to not make me cry.
  16. The Only Thing - Sufjan Stevens, "and also anything by The National"
    Suggested by @michael_circa91
  17. Bittersweet Genesis for Him and Her
    By Kishi Bashi • "Critically acclaimed but sadly underrated, fortune definitely favored us but no one celebrated." If you haven't listened to Kishi Bashi yet, you need to.
    Suggested by @leighton
  18. Little Did I know or anything by Over the Rhine
    V good for driving home crying on summer nights
    Suggested by @colleenpagaard
  19. Pictures of You
    by Angie Hart
  20. I Hurt Too
    by Katie Herzig
  21. The Scientist
    by Coldplay. Forever.
  22. Maybe God is trying to tell you something from the Color Purple Sdtk
    Suggested by @shanaz
  23. Hurt
    by Johnny Cash. Another obvious choice haha. It's a cover of a Nine Inch Nails song and it's reaaalllllyy heavy.
    Suggested by @gagneet