You Can't Be 20: Old-Person Songs by Young People

"I think people in their mid-20s are often more nostalgic for childhood/teen years than older folks"

interesting topic and thread. I wonder if Simon Reynolds dealt with this phenomenon in Retromania (which I read when it came out but that was some time ago).

agreed, great revive.

Tangled Up In Blue seemed vaguely Deep to me as a younger person, never one of my faves but I dug it. at 42, i find it a lovely mix of goofy Dylan shaggy-dog stuff and a near-magic encapsulation of this sense of having a personal Past. i bet it works whether you've moved around a lot, stayed in one place, become a carpenter's wife, whatever.

Still Crazy has less incident and it's not nearly the same kind of a Rorschach blot, but is so beautifully polished, especially the first verse. it gets at something.

Not quite the same thing, but I had always assumed Jimmy Buffett's "A Pirate Looks at Forty" was at least semi-autobiographical, but it turns out he recorded it age 27.

Billy Stayhorn was 21 when he wrote Lush Life. It was a self fulfilling prophecy because he did become an alcoholic. It has the most depressing, world weary lyrics of any jazz standard i can think of and it shocked me when i learned how old he was when writing it.

Tangled Up In Blue seemed vaguely Deep to me as a younger person, never one of my faves but I dug it. at 42, i find it a lovely mix of goofy Dylan shaggy-dog stuff and a near-magic encapsulation of this sense of having a personal Past. i bet it works whether you've moved around a lot, stayed in one place, become a carpenter's wife, whatever.

otm

I love "Tangled Up in Blue," and in the regular world, Dylan being in his early 30s at the time would still count as young; in a pop music context, less so. Like another song I thought of and decided it was something different: Madonna's "This Used to Be My Playground" (she was 34).

I'm going to posit that Madonna had been through a few things by the time she was 34.

She was tangled up in true blue.

Lol clemenza

I was just listening to Dion and the Belmonts singing “September Song” from 1960’s Wish Upon a Star album and thinking they sound much too young to sing those lyrics. But my benchmark of an appropriately grizzled performance is Willie Nelson’s 1978 recording and he was only 45 when that came out, which now seems a bit young for that death-haunted song.

Willie Nelson is an interesting case. He was already old when most us were born, and he is apparently immortal.

When he was relatively young, and wrote "Crazy," dinosaurs still roamed the plains. It's a bit weird to see pictures of young Willie, because his brand and image have solidified so much into the one we know.