I think that I paid $1 to see Ted Nugent play, but I could have gone for free because I was friends with almost all of the guys working the lights and back stage.
Speaking of getting to see great artists for almost nothing I saw Philip Glass and his Ensemble at a high school gym for just a couple of dollars back in the early 1980's. The next night I was eating dinner in town and he and a couple of his players were sitting at the next table. My wife kept poking me in the ribs to introduce myself and say what a big fan I was, but my inclination was to leave the guy alone.
I also got to see Chuck Leavell (Rolling Stones "stunt" keyboardist for many years) play with his group "Sea Level" (OMG, what a bad pun) at a bar in Champaign,IL, with about 15 people looking on, for FREE.
All of this pales compared to sitting next to Bo Diddley on an airplane ride and talking music for a couple of hours. It was great until the other people around us figured out who he was. It was like a switch went on and he went into what I can best describe as "dealing with 'fans' (especially white)" schitck. It was funny, but you could tell that the whole thing was well rehearsed.