Toeing the line between sadness and joy, yearning and nostalgia, some music just punches you in the gut. Here's a playlist:
  1. "Alison" by Elvis Costello
    This song is wry and witty until it just stabs you. I fall to pieces. "I'm not gonna get too sentimental like those other sticky valentines / cause I don't know if you've been loving somebody, I only know what isn't mine."
  2. "Moon River" by Audrey Hepburn
    Hopeful and hearbreaking
  3. "Peach, Plum, Pear" by Joanna Newsom
    Joanna Newsom tells stories, and this one takes you from meet-cute to heartbreak as the whimsical and eerie chords play behind.
  4. "Goodbye Stranger" by Supertramp
    "Goodbye stranger / it's been nice / hope you find your / paradise"
  5. "Hey Mama" by Kanye West
    RIP Donda West, this one hurts
  6. "She's Not Me" by Jenny Lewis
    Like Costello, Lewis' lyrics are full of wit until you hear "She's not me / she's easy"
  7. "Nightswimming" by R.E.M.
    The first few notes on the piano are enough to make you beam and sob
  8. "Our Deal" by Best Coast
    "I wish you would tell me / how you really feel / but you'll never tell me / cause that's not our deal"
  9. "Calendar Girl" by Stars
    "The pages keep turning / I'll mark off each day with a cross / and I'll laugh about all that we've lost" The best at this sensation. @xtineengels
  10. "You Belong to Me" by Patsy Cline
    Such a lovely song until you listen and feel the longing in Patsy's voice. Amazing
  11. "The Book of Love" by the Magnetic Fields
    Really their entire "69 Love Songs" album
  12. "Dream a Little Dream of Me" by The Mamas and the Papas
    A classic covered by many, Mama Cass just transforms this into one that will get you welling up
  13. "A Change Is Gonna Come" by Sam Cooke
    RIP Sam Cooke. This song is an inspiration but also a solemn reminder of how little progress we've made since it was written
  14. "Changes" by David Bowie
    "Turn and face the strange ch-ch-changes"
  15. "We Will Become Silhouettes" by The Postal Service
    The music is bright and light electronica juxtaposed by "We will become / silhouettes when our bodies finally go"
  16. Every Fleetwood Mac and/or Stevie Nicks song
    "I've been afraid of changing / cause I built my life around you" "But listen carefully to the sound / of your loneliness / like a heartbeat drives you mad / in the stillness of remembering what you lost / and what you had" Stevie is the master of this and that's why she's the best!
  17. "Naked As We Came" Iron and Wine
    It's sweet and beautiful, but the lyrics are honest. "I lay smiling like our sleeping children. / One of us will die inside these arms. / Eyes wide open, naked as we came"
    Suggested by @annalara
  18. When She Loved Me by Sarah McLachlan
    Suggested by @josella
  19. Alone Again (Naturally) by Gilbert O'Sullivan
    Suggested by @tmarchewski
  20. "Umbrella" Rihanna f. Jay-Z
    "When the sun shines, we'll shine together / Told you I'd be here forever / Said I'll always be a friend / Took an oath, I'ma stick it out till the end". Also I think the chord progression in the chorus directly taps into all of the emotion centers in my brain.
    Suggested by @ladyprofessor
  21. "Bobby Jean" by Bruce Springsteen
    Maybe you'll be out there on that road somewhere / In some bus or train, traveling along / In some motel room there'll be a radio playing / And you'll hear me sing this song
    Suggested by @katya
  22. "Cats in the cradle" Harry chapin
    Suggested by @pcutler99
  23. "Dear Old Friend" by Patti Griffin
    Suggested by @maretorliss
  24. The First Time Ever I Saw Your Face, Roberta Flack
    At some point in the early 80s, my Dad discovered this song and played it over and over and over, as he transcribed the lyrics. It perfectly describes his feelings about my Mom. Drove me batty at the time because I was 11 or 12 or 13 and I knew the song sucked. Now, 18 years after my Dad died, I think of my parents and remember my Dad transcribing the words the captured his One True Love. Happy tears all the way!
    Suggested by @lambikins