this post was submitted on 20 Jul 2023
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Some classics I didn't see here yet:
Pink Floyd - Wish you were here (all the songs from that album, come to think of it, are in the second person and usually pretty specificially talking to Syd Barrett)
Bob Dylan - Like a rolling stone
Now for a completely different take on "feeling like a conversation", I have an instrumental recommendation: Bernstein and Brubeck - Dialogues for Jazz Combo and Orchestra
Edit: just noticed that a lot of songs by Steely Dan are also in the second person, usually directed and criminal or tragic figures. Kid Charlemagne is my favorite in that format.