So, I’ve decided to do this facebook 30 Day Song Challenge (you can see previous days here)thing and I figured I’d do it here on ninebullets. Feel free to contribute your thoughts in the comments section. So, without further ado:


Ever since Brian explained the origins of this song I don’t even listen to it anymore. It’s incredibly sad and I sometimes feel like an asshole for listening to it.

Lucero – Darby’s Song

So, how about you? You got any songs that make you sad?

17 thoughts on “30 DAY SONG CHALLENGE: DAY 4:”

  1. I agree with you, I can’t listen to that song anymore, it’s just too sad. I skip it every time it pops up.

    Anyway, I’m doing this challenge too, and I chose Justin Townes Earle’s “Yuma” as my selection for this one. It’s a brutal listen.

  2. David Wiffen’s Driving Wheel, performed either by Tom Rush or The Black Crowes. Brings me down every time. Love it, though.

  3. Tim Barry’s “222”. Reminds me very much of a friend of mine who is no longer with us.

  4. Tim Barry “Wait at Milano” – The guy just sings with so much passion and emotion.

  5. I had an instant response to this one: Johnny Cash’s “Spiritual”. I love singing along to Cash songs, but I always get a lump in my throat when singing to this one.

  6. Definitely the easist one of the challenges yet for me. It has to be Pineola By Lucinda Williams. So close to an experience I had with one of my best friends, reminds me of Rusty every time I hear it. RIP my brother.

  7. Mine is out of the genre so to speak but it reminds me of an easier time that wasn’t all that happy along with my best friend and too many nights at sketchy pool halls. Too many stories behind it and even though it’s cheesy it is:

    Pearl Jam – Black

  8. “Where Were You” Alan Jackson. I cannot listen to that song without getting emotional

  9. Johnny Cash’s version of the Nine Inch Nails song Hurt….makes me tear up every time I hear that last verse

  10. that one is pretty awesome. I think I’ve written about this on here but I think Johnny stole that song from Trent. Like, when someone says, “All Along The Watchtower”, you immediately think Hendrix despite it being a Dylan song. Yeah. I think in 10 years it’ll be assumed that it Cash’s song.

  11. i’ll follow you into the dark by death cab for cutie reminds me of that girl that got away. great song.

  12. “Adagio for Strings” is universally regarded as the saddest musical piece ever written – I can’t argue with that sentiment.

  13. Tim Barry “222” & “Wait at Milano” are 2 that ALWAYS make me full on cry, took everyhting I had not to do it in front of him.
    William Elliott Whitmor, “Hell or high Water” is a happy kind of sad if that makes sence.

  14. Tim Barry “222″ & “Wait at Milano” are brutal but there’s another one of his songs that got me. There’s a live version of South Hill from a show in CO where a few veterans jumped onstage and sang it with Tim. It’s amazing. I’m not sure if it’s still true but for awhile after that he wouldn’t play the song anymore because it could never be that good again.

    Darby’s Song and the story behind it are heartbreakers as well. It annoys me to no end when people insist on requesting it at shows.

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