Paul Butterfield Blues Band, Fillmore West, 1968. I think these were the first shows Bill Graham produced after moving from the Fillmore to the Carousel Ballroom and renaming it Fillmore West. I want to say I remember this as a great show, but ... Mike Bloomfield had left the band, and the other acts on the bill (Ten Years After and Fleetwood Mac) featured a lot of showy guitar work that impressed my 15-year-old self, so I didn't appreciate the Butterfield Band as much as I might if I could go back in time. Here's an Elvin Bishop showcase from that time ... he, too, left the band by the end of the year.
Bob Dylan, Oakland Coliseum, Concord Pavilion, 1974, 1978, 1998. If I remember correctly, the 1974 show was the first concert my wife and I attended together (we'd been married about 9 months). This was the tour with The Band, and it was easily the best of the three times I've seen him. 1978 was the Street Legal tour where Dylan seemed to channel Neil Diamond, and 1998 was a fine triple bill with Van Morrison and Lucinda Williams where for my money Dylan came out third.
Here is a decent-sounding bootleg of the 1974 show:
Here is one of the more memorable songs from Street Legal:
And here is an audience video of Bob and Van from the 1998 tour:
Shannon Wright, Fillmore, 9-23-02. She opened for Sleater-Kinney, and I recall her as being very energetic on stage. Can't remember any of her songs all these years later, but at the time, she made an impression. Here she is in 2002 ... not sure this does her justice: