I couldn't possibly narrow it down to five. How about ten?
- The Band, Berkeley (CA) Community Center 1969
- Rockpile & Moon Martin, The Country Club (Reseda, CA) 1980
- Dave Edmunds, NYC 1982
- Marshall Crenshaw (5-piece), NYC 1982
- Phil Seymour, The Country Club mid-80's
- Big Joe Turner, Club Lingerie (Hollywood, CA) mid-80's
- The Lyres, Club Lingerie late-80's
- NRBQ (w/Al Anderson), The Roxy (Hollywood) mid-90's
- Iris Dement, The Roxy and The Troubadour mid & late-90's
- Bob Dylan, The Pantages Theater (Los Angeles) 2002
This is leaving out my first two shows, shows which might be at the top of a lot of peoples lists: The Beach Boys at The San Jose Civic Auditorium in 1964, and The Beatles in San Francisco in 1965, which were, in comparison to the above, merely okay. Sorry The Beatles worshipers, they were not so good live.
The one show I now dearly would love to have been at is Dylan w/The Hawks (aka The Band) at The San Jose Civic Auditorium in 1966. The Beatles in '65? The Rock n' Roll paradigm of the past. Dylan w/The Hawks in '66, the future. Two friends of mine were at that Dylan/Hawks show, and were also at number one on my list with me. They were ahead of me in '66, but by '69 I had caught up!