Some really interesting answers and trends here: “Puff the Magic Dragon” apparently a real tear-jerker for a lot of people, as well as “You Are My Sunshine”…https://twitter.com/anamariecox/status/1152305298851409926 …
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It only occurred to me now, hours later, that one reason outlaw country gets me in the gut is that it was the music my mom introduced me to—it’s the soundtrack for a time before we got lost in booze and far from each other… a fitting plot for a country song.
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Hail to the Chief (since January 2017)
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"The Dance" - Garth Brooks. I know it is not supposed to be sad per se, but a happy reminder that you took the chance anyway. Fear god do I sob when I hear it.
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Pancho and Lefty is heartbreaking as f. Heh
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“Pancho needs your prayers it’s true / but save a few for Lefty, too” just *destroys* me
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“Baby Mine” from Dumbo.... for decades it has made me cry.... starting with the original movie. (Yes I am old)
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"The Little Drummer Boy" "I have no gift to bring/Iplayed my best for him"
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Oh, wow, that one can get me, too. *I think I might get triggered by stories of people who struggle but miss the mark.*
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Cats in the Cradle - Harry Chapin
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