Please add to this so I can increase the length of my depressing playlist
  1. Skinny Love//Birdy
    Especially Birdy's version. It's so emotional and if I'm already sad it's going downhill fast for me
  2. Rivers and Roads//The Head and the Heart
    Thinking about college and leaving friends I've known my whole life + this song ends in many many tears
  3. The Funeral//Band of Horses
    Never ever ever ever listen to this if you are already sad/ right after you hear horrible news. Especially not on repeat(idk why I did that I guess I felt like being miserable)
  4. Let it Be//The Beatles
    Beautiful song/ beautiful people get me emotional sometimes so yeah
  5. Turning Page//Sleeping At Last
    Most real/sad love song I've ever heard (besides skinny love)
  6. 5AM//Amber Run
    Trust me. Tears for days.
    Suggested by @SpaceCase
  7. No One Is to Blame//Howard Jones
    A few years ago, I was driving with my mom and this song came on. She started to cry and said that she missed her mother. So now I cry whenever I hear it.
    Suggested by @biz
  8. When a Heart Breaks by Ben Rector 😭
    Suggested by @chrisfon
  9. Hallelujah//Jeff Buckley
    His inhale before he even starts the song makes me tear up. I've morbidly told my sister I want this song played my funeral and can no longer listen to it all the way through.
    Suggested by @michellejennifer
  10. 100 Years// Five for Fighting
    Has kind of a bittersweet feeling & it was played as part of a playlist on loop at the calling hours/visitation of a young man I went to years ago
    Suggested by @kate81
  11. Time For You// K.Flay
    I've literally just sat on my floor and cried listening to this song 😿
    Suggested by @sesealyah
  12. She Don't Love You/ Eric Paslay
    Something about his voice gets me
    Suggested by @Marna
  13. Argue with Heaven // David Ramirez
    I actually cried in the library to this song while reading about Alexander Graham Bell's death for my history class. It was a weird moment but such a great crying song!!
    Suggested by @calliestorie
  14. Hot Gates// Mumford and Sons
    Honestly most songs by them make me cry. But this one rips my heart out a bit. Amazing lyrics that are very heartfelt and honest
    Suggested by @libby92
  15. Overs - Simon & Garfunkel
    "And I'm habitually feeling kind of blue, but each time I try on the thought of leaving you, I stop...I stop and think it over."
    Suggested by @avecsarah
  16. River - Joni Mitchell
    Captures my yearly Christmas melancholy.
    Suggested by @avecsarah
  17. "Clam, Crab, Cockle, Cowrie - Joanna Newsom
    Suggested by @poly
  18. November rain // guns & roses
    Suggested by @imc
  19. Skinny Love//Bon Iver
    Suggested by @margaretmae
  20. Saturn//Sleeping At Last
    I cry. Every. Single. Time. The opening notes on violin are too beautiful and the message is so sweet.
    Suggested by @bredee
  21. "Adam McCarthy" by Ralph Covert
    An ode to the song-writers friend who was dying and then died of cancer and he was WAAAYYY young.
    Suggested by @jeffnewman
  22. Medicine - Daughter
    this whole album actually completely destroys me. if you ever need a good sob, this is where you should go.
    Suggested by @aesthetic
  23. Five Years - David Bowie
    I cried when I first heard this song years ago. Now that Bowie has passed away, it's become even more emotional for me.
    Suggested by @MatthewAlmont
  24. So This is Goodbye
    William Fitzsimmons
    Suggested by @margaretyoko