When I was a kid growing up in northern Manitoba in the 70s, I played Mom and Dad's 8-track of Lightfoot's Don Quixote over and over. I wouldn't consider myself a huge fan of folk or country music in general, but Lightfoot transcended genre with music and lyrics of great sensitivity, grace, and power. His songs told stories that rang true and evoked powerful emotion.
Regarding Don Quixote itself, the title track is exquisite, and I love "Alberta Bound," and especially "Brave Mountaineers," but "Looking at the Rain," linked above, is just...transcendently sad and mournful, soulful and gorgeous, and I can't help but sing along and cry every time I hear it. It's the song I hope survives civilization for aliens to find so that someone out there knows that humans were capable of creating something so timeless and magical.
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