Mood:  caffeinated

Some of the notable shows from my list for specifics:
Bob Dylan and the Grateful Dead was my first-ever concert. July 4, 1987, Foxboro Stadium. Now that's an indoctrination.
I saw the first Lollapalooza tour (Jane's, Living Colour, NIN, etc.).
My two Dave Matthews Band shows were when they were opening for The Samples at the Orpheum in Boston and State Theater in Portland, Maine - 1993 or 1994 I think. Yup - blew my friggin' mind. Best opening band ever.
I first saw Neil Young in 1991 in Tampa, Fla. He was awesome, touring for Ragged Glory, and still on that Freedom high. Sonic Youth and Social Distortion opened. Social D played 5-6 songs and was awesome, though I was bummed the set was so short. Sonic Youth came out, played "Kool Thing" and then launched into some distortion/feedback thing, placed their guitars next to the amps and left the stage. It was five minutes of song, about 10 minutes of them making noise, and then another 30 minutes of noise generated from their abandoned instruments. Sucked.
The second time I saw Neil Young was with my wife when he toured for his Glendale concept album. It was fantastic. After doing the whole album, complete with set design and actors performing on stage to the story, Young's "encore" was 30 minutes of his most popular tunes.

And I was working sound for a friends band, who managed to get an opening gig for a Roomful of Blues show (roughly 1997). So to work sound in a nice opera house, meet some cool sound techs (who knew more and could do more with a pinky finger than I ever knew), and hear Roomful from the board (best place to hear live music) was pretty neat.

One of the most interesting concerts I ever attended had a rather sparse crowd. I was booking music into an inn. It was presented by my magazine, the artist got the door and the inn got food and beverage sales. There's this fantastic singer-songwriter from the Boston area that I wanted to introduce to this market I was in. Eric Colville is his name. Well, long story short. Eric played for me and my wife. No one showed up that night. I was overconfident that the pedigree of past shows would offer trust to those audiences to try this show out. I should have booked Eric as an opener for someone else, but ultimately it was awesome. Eric is a genuinely nice guy, a great songwriter, and his first CD is a personal favorite. So my wife and I have this great memory of having a private concert.