I thought I would have trouble with this category but it turns out it is slowly become a top 10 list.
1. Carmina Burana at Tanglewood (July 13, 2001). My friend Dave used to sing with the Boston Symphony Orchestra a lot. For a year or two, he would spend the summer working at Tanglewood, which is one of the most amazing places to hear music on our fat little planet. So he got posh housing and we'd sit on the lawn outside on our Therm-a-rests listening to amazing music. But on the occasion I site here, Dave was singing Orff's classic Carmina Burana with the BSO at Tanglewood. For those of you who can't remember the song or don't know what it sounds like, it was the song playing in the Guinness commercial featuring the train (turn up your volume for this link). The piece is about 25 minutes long and the hairs on my neck were on end for the entire duration. I have never been as moved, engrossed, and convinced that the world was exploding more than that night under a clear and open Massachusetts sky.2. Radiohead at Harbor Lights (August 27, 1998). Not only was it the first time in a few years that the band played their most well known song (to that date) "Creep," but it was a show the band even looks back on and remembers as one of their best. Given the fact that OK Computer had just come out, it was a great time to be a Radiohead fan. As far as location, it didn't get much better. The Harbor Lights pavillion sat right on Boston's scenic waterfront and would host amazing bands despite limited seating. So it was almost like a club, but outdoors, and with the energy of a stadium. This one always comes to mind as I remember so vividly gettting close enough to see the odd electronic bracelets that Johnny Greenwood wore to coax sounds from his guitar known only to other galaxies. It was like seeing the inner organs of superhero laid out before you and shown how everything works in great detail.
3. R.E.M at Great Woods (June 16, 1995). Looks like we're approaching a ten year anniversary on this one. Huh. I have a picture of my friends and I at this show and dare I say I barely look or feel a day older now. I still talk to many of the kids I went to the show with, which was my first major concert, and my first time ever seeing R.E.M. - the tickets were $75, which adjusted for America's inflation and ticketmaster's inflation, it would be roughly equal the GDP of many 3rd world nations in today's dollars. This was also when Monster came out, and R.E.M. sought to be/be on the cusp of something important in music. Didn't really happen though. However, I saw my music idols on stage and finally knew that they were real, that they played their instruments, and that I was 15 and my life seemed less complicated for a few hours. And at 15, that's hard to do.
4. Ben Folds at Avalon (September 16 or 17, 2001). Notice the date. This was back in that period of the week after September 11 where the world did not know if it was OK to do stuff yet. We got these tickets for free because I knew the owner's wife well, but we weren't sure if we should go to the show, because it felt inappropriate - there was still a rawness to everything. However, we went and it was an amazing show - aided by the fact that I name dropped the owner's wife and assistant and within 20 minutes, we are up in the booth overlooking the show and having drinks with the record label and industry folks while sitting in plush couches with Ben Folds rocking the shit out of the place. There was dancing, drink spilling, and sing-a-longs that dulled the 9/11 feeling that was waiting to greet you upon exit. It was respite care as far as I'm concerned, and I thank Ben Folds for it.
5. Ely's Gin at JT Kaminski's Wedding (can't remember the date). I can't remember what year my friend JT got married, but I am pretty sure it was sometime between 2000 and 2002. JT and his bride Tessa invited all of their friends to their backyard where they were getting married. Not only does it make my Top 5 Wedding List, but the fact that a group of our friends were the wedding band made it amazing. Ely's Gin was a collection of some of my friends from high school who wrote music well beyond their years. Imagine if Rush, Creedence Clearwater Revival, The Who, and Mr. Bungle all had a bastard child, and no one wanted custody. They rocked the hell out of Massachusetts for a good number of years. I am lucky enough to have recordings, because there are few out there these days. Anyway, they played every song we knew, every song we wanted to hear, and as usual, the great covers. They were the perfect wedding band, and you could go up and grab an instrument and jam with them. It felt like the first wedding I went to that was thrown for ME.
Honorable Mentions: