Wow, great topic.
I'm guessing I may come back with some edits as I think about this more, but off the top of my head:
- SRV outdoors at Auditorium Shores in Austin in 1989.
- U2 on the 360 Tour at Soldier Field (this was a re-do after we saw them at Cowboys Stadium in Dallas earlier on that tour and quickly realized what an AWFUL venue it is for a concert with the roof closed).
- Billy Joel at MSG in 2014 and 2015 (have been blessed to see him many times, but in front of the "home crowd" in NYC it's just a different experience).
- Andrea Bocelli at the Frank Erwin Center in 2013 (I think that was the year).
- My fifth would be a tie between Paul McCartney at Minute Maid Park, Lyle Lovett every time I see him, Diana Krall at a theater I can't remember the name of in Santa Rosa (CA), every ACL Music Festival I've ever attended (Stevie Wonder, Al Green, The Mavericks, Los Lobos, Texas Tornados, etc.), and at the Texas State Fair back in the late 1980s after Texas beat OU when I caught this up and coming country star named Garth Brooks on a trailer stage with about 200 other people.
(Sorry, I know that last one was cheating a bit.)