And of course, Jackie Gleason—yes, THAT Jackie Gleason—with one of the biggest selling albums of his day. Music for Lovers Only!
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This is great and not too long ago, I listened to one of those Jackie Gleason orchestra(?) albums, this is probably his most famous one that you posted but another one I listened too as well. It checks all the boxes for being "music for squares".
Per Washington Square, it belongs here... those vocals and some versions also actually, imho, put it in the "folk music" category, there were a lot of good folk songs in the day and I don't consider a lot of that for squares but a lot of it fits in here. I toyed with a "folk music" thread but I don't know the music well enough, sure, Dylan, Baez, Seeger, Kingston Trio and so on probably fit that.
We have a "folk music" store here, I've window shopped on but have never gone in. It looks like instruments, sheet music and such. I don't know what else they might have but I don't want to push that distinctly different category into this one too much though, there can be some overlap.