Peggy-O, by the Grateful Dead.
We’ve established I’m a sucker for a story song, and I’m not above calling this song somewhat cover-of-a-cover-adjacent, since the origin story is some flavor of Scottish folk song, if you believe Grateful Dead forums and Wikipedia. Maybe I should just be tagging some of these as “traditional” and leave it at that.
Sophomore year of college, when there was a lot of Dead flowing, the Deadest-head in the dorm room who brought it all to light for us got a giant book of Dead lyrics for the holidays or a birthday, I think, (with some pre-wiki explanation and context, IIRC), and I remember spending some fond hours with it.
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Regarding the crack about the hat at the top of the recording: I wasn’t the one who went into the attic of the hotel suite in Eastern New Mexico to see what was there, and I definitely wasn’t the one who removed the hats, but I was the one who staked a claim on the black one, and that has made all the difference. Also, I nearly drove myself delirious from dehydration when I wore it on a 100 degree desert working outdoors in double-knee Carhartts, as one did in the middle of the year 2001.