Best concert probably Ozzfest 98. SOAD was on the side stage, I had no idea who they were but they were killing it. Sevendust was there, then Tool opened for Ozzy. People were passing pinners while you waited in line to get in, it was an all day concert. Good times.
Worst concert Earth Day Birthday 2008. Even with the girls finally putting pasties on and painting themselves instead of wearing shirts I don't remember enjoying any of the bands. Spent the whole day on a blanket waiting to go home.
Bucket list would be a Jimmy buffet concert on the water in the Keys. Everyone floating in boats and drinking and having a good time.
In 2000 I could have gone to see U2 and I think it was the Lemon tour, my cousin went to Tampa and saw it, said it was fantastic.
Oh and props to the Tans-Siberian orchestra we went 4 years ago in December and had a good time there. Definitely something to do at least once.