The Dave Matthews band in November of 1991. It was free beer night at Ziggy's, which is probably the best live music venue between atlanta and dc, and is the stop for bands of a certain size. I was recording the show, and counting me, there were 7 people in the audience. And two dogs. The two dogs were having sex in front of the stage. Dave spent a few minutes discussing this.
X with Billy Zoom at the 9:30 club. Before the show began, my wife and kid and I are hanging out in the balcony seating area, and up walks Billy. He told us how much he missed his kids, and proceeded to spend about 15 minutes playing with Thomas. The show was pretty good, too...
The Flaming Lips at Diamond, in Oklahoma City, 1995. We'd driven from NC to Dallas to see the Flaming Lips at Trees, then went up to OKC to see the tour ending show at Diamond. The band found out how far we'd travelled, and had us brought backstage after the show. Wayne offered to let us sleep on his couch, and Ronald introduced us to his parents. We got to hear Wayne tell the story of prank calling the local record store in norman after the proprietor had discovered a head in his dumpster (Norman's first murder in a LONG time).