8 Heartbreaking Songs

One of my friends from college posted a link to Entertainment Weekly's "50 Most Heartbreaking Songs of All Time". I'm neither ambitious nor diverse enough to come up with 50, and I'm not conceited enough to think my choices are "of all time". However, here are 108 songs that make me tear up a little every time I hear them. (And you can use either version of "tear" that you wish.) (As always, in no particular order.)

Note: Links are to Amazon. If you buy any of the songs, I get a cut.

  1. "Hallelujah (Live)" by Jeff Buckley
    This song so forlorn and plaintive that it moves me each time I hear it. A friend who I've lost touch with introduced me to Jeff Buckley.
  2. "Hurt " by Johnny Cash
    Trent Reznor's version of this is from such a different outlook, and it's one I don't identify with very well. But Johnny Cash was singing about the love of his life and the damage he'd done to that love over time. His voice sums up the pain of years of trying and frequently failing and of wanting so badly to get it right.
  3. "Breathe" by Melissa Etheridge
    This song ran through my head again and again when we were at the hospital with Aiden. To this day, my mind goes back to those hours of trying to find strength to get through the hardest days of my life.
  4. "Whiskey Lullaby" by Alison Krauss and Union Station
    I don't really know why this song resonates with me the way it does. But I think that the slow dull pain of losing love is one of the more terrifying things to contemplate.
  5. "Mama's Arms" by Joshua Kadison
    The album this song is from was one TBWITWW and I listened to frequently when we were dating (the first time). I can't imagine the pain of losing a parent even now, let alone as a child.
  6. "Taps"
    Both of my grandfathers were veterans. The simplicity of this song is both a hymn and a lament. Those who lay down their lives (or any part of it) to preserve the rights we have deserve every honor we can give them.
  7. "Bang the Drum Slowly" by Emmylou Harris
    I lost one of my grandfathers when I was too young to really understand what I missed in not knowing him better. I lost the other shortly after Aiden passed away. Even though I grew up within a few miles of both of them, I never learned as much about them as I wish I could have.
  8. "Walking On Sunshine" by Katrina and the Waves
    There's nothing actually sad or heartbreaking about this song, unless you've seen the episode of Futurama "Jurassic Bark". But if you have...

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