Went to a ton of shows in the '80s and '90s, not sure what I'd pick.
Saw most of the Grateful Dead shows in NY/NJ/Philly from about '88 to '92. The band wasn't the greatest then but it always a good time anyway. Lots of punk and metal shows in the mid/later '80s. Ramones in '85, Black Flag, Metallica, Slayer, Anthrax, The Cult, Exodus, Manowar, Bad Brains, and a million more. That Bad Brains show sticks out, The Ritz NYC in 1986. The band and the crowd were on fire, like one giant wave/mosh pit from front to back, and The Ritz was a pretty big place. Just double checked the date and it seems like there are some videos of it, cool!