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30 Day Song Challenge – Day 27 – A Song That Breaks Your Heart

Today’s challenge invites us to share a song that breaks our heart. If I’d looked ahead on these challenges, I might have saved the Glen Campbell song I posted on Day 10 for “A Song That Makes You Sad” for this, and chosen a different sad song then. But since that’s under the bridge, here’s another song about heartbreak, and specifically about that moment in a long-term relationship when you realise things maybe aren’t going to work out in the end. I’m happy to say that it’s been a very long time since this song resonated strongly with me, but back when it did, it certainly was a time of tremendous heartache. Here’s Christine Lavin with “Katy Says Today Is The Best Day Of My Whole Entire Life”


30 Day Song Challenge – Day 26 – A Song That Makes You Want To Fall In Love


30 Day Song Challenge – Day 28 – A Song By An Artist Whose Voice You Love


  1. Jim Poltrone

    It’s a tossup between this and “If I Could Change Your Mind” — one of the few APP songs featuring a female vocalist (the late Lesley Duncan).

    • Lee Billings

      That’s definitely capable of more than one interpretation. Listening to it now, I hear someone trying to get his hooks back into a woman who finally managed to get out of a really bad relationship. Sylvia has her mother running interference for damn good reason.

    • Daniel Reitman

      I saw a documentary last year in which it turned out the woman who inspired Shel Silverstein thought of him as a friend

  2. Bruce Adelsohn

    Another no-brainer for me. Can never get through this without requiring a unicorn chaser. https://youtu.be/UI7ZfYabVkg

  3. Patricia Jones

    Having children myself, hearing this song about parents attempting to cope with the death of a child breaks my heart everytime I hear it. https://youtu.be/86I9faiiFBI

  4. Neill Mitchell

    Tori Amos’s cover of Tom Waits “Time” -- Gets me every time, and I’m not quite sure why.https://youtu.be/gtythil5qwY

  5. Stephanie Riehle Craven

    Certainly the first time I heard this, I wept. And even still it shakes me up to hear her sing about the love of a child. Joni Mitchell’s “Little Green.” https://www.youtube.com/watch?v=dvhdKywbcJ0

  6. T J Burnside Clapp

    I almost needed therapy after hearing this one. My oldest brother died at about the same age, and it tears me apart to think about what my parents went through. 🙁


  7. Bruce Adelsohn

    Also, this one. I can’t imagine being on either side of this situation. https://youtu.be/FivgslDNqf8

  8. Paul Kwinn

    Yep, I might have swapped this with my “sad” song, too. But still, here’s Pete Grubbs, to depress you: https://www.youtube.com/watch?v=nu1tsJJ-mK8

  9. Juanita Coulson

    “Hills of Ixopo” from ” Cry, The Beloved Country”.

  10. Dell Christy

    I still have tears when I listen to this. https://youtu.be/q490NYHBytg

  11. Laura Law

    Christine Lavin is one of my faves.

  12. Lee Billings

    I can’t listen to this without crying. The destruction wrought by well-meaning friends, and the joy turned to ashes. https://youtu.be/fWqj_tC9jrU

  13. Laura Gallagher

    Since I already gave you It’s Quiet Uptown for that earlier one, I give you this one. I so wish I’d had this sort of support through our moves as a kid. https://www.youtube.com/watch?v=Q8-MKOs9meo

  14. Carolyn Fortuna

    This song makes me wistful and sad for simpler times with my family long gone. https://www.youtube.com/watch?v=dcnd55tLCv8

  15. Heather Munn

    We keeping loosing too many good people, good musicians, good kids, to drug addiction:

  16. Manny Jacobowitz

    That’s a tough one. Could say Sondheim -- Send in the Clowns, or, One Hand, One Heart. Or Sunrise, Sunset from Fiddler, now that I’m a parent. But for sheer pain and need, imma go with one most of your friends won’t know already:https://www.youtube.com/watch?v=0YONAP39jVE

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