Arlo Guthrie - my parents took me and my brothers to see him in ~1975 when I was 8. My parents were scandalized that a couple sitting one row in front of us were snorting white powder off a small mirror. Took years for me to realize they were doing coke.
The first concert I went to deliberately was Tom Petty and The Heartbreakers with Bob Dylan in 1984 at Madison Square Garden. Dylan’s career was at a nadir and Petty went on tour with him to support Dylan by introducing his fans to Dylan’s work. Dylan didn’t do himself any favors because he was awful live.