A List of Sad Songs

First post in a long time, but was compelled by a conversation with my friend J. We were discussing some of the saddest songs we’ve heard, so I’m listing a few off the top of my head. There are definitely plenty more that take on all sorts of heart break. These are amongst the ones that hit me hardest.

  1. Jason Isbell – Dress Blues: Describing the unexpected losses of war and the impact on an entire community.
  2. The Bee Gees – I Started a Joke: A song often sung by some soldiers in Vietnam, this song takes on a whole new meaning
  3. Al Green – How Do You Mend a Broken Heart: another song written by the Gibbs, a lot of it is just the way this song is sung by Green that makes it intensely emotional.
  4. Death Cab for Cutie – Tiny Vessels: I could have listed about five songs for DCFC that are sad. This is the one that has been the most relevant to me. If you’ve ever been on the end of a breakup that you don’t understand, this song is for you.
  5. Ra Ra Riot – Dying is Fine: When thought of in the context of the death of their drummer, John Pike, this song takes on a whole new meaning.
  6. Jars of Clay – Fly: A song written for a woman who had cancer, and her husband who promised never to let go of her hand until she passed away.
  7. Rachael Yamagata – What if I Leave: A song about a relationship in its death spiral, and having the strength to walk away.
  8. Vic Chestnutt – Flirted with You All My Life: At first you think the song is about the inability to gain the affections of a woman, but then you realize he’s flirting with death and suicide. Particularly sad in the context of his eventual suicide. This song will make you shiver.
  9. Journey – Don’t Stop Believin’: This is more to do with the song’s potential to be sad. If you slowed this song down substantially, it can become a very depressing song. It goes to show that how a song is played makes a huge difference on how it’s interpreted.
  10. Ben Folds Five – Brick: Ben Folds’s experience of assisting his girlfriend with getting an abortion. Non-political, and just reaffirms that an abortion is never an easy decision.

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