Ramblin' Jack Elliott, one-on-one. This has to be at the top of the list. I saw Elliott many times at the Ash Grove in LA in the 60s. In the 80s I got to meet him more personally when his girlfriend got sick as they were driving past Portland, and she ended up in the hospital here. Jack parked his Winnebago in the parking lot of the Gypsy bar. I met him, interviewed him for the weekly paper and arranged a quick concert at the Earth Tavern on 21st Ave. (it no longer exists). I helped him set up and do a sound check on a Friday afternoon, after which Jack sat on stage, I sat alone in the performance space, and Jack asked, "What do you want to hear?" What followed was almost an hour personal concert, with Jack doing full renditions of each song I named. How can you beat a concert like this, from one of your all-time favorite musical artists? 
Tom Lehrer at Stanford. I mentioned this recently. It was in 1958, I think. What made this special were several things: I drove with two friends from LA to Palo Alto in my family's car, the first time I was "trusted" with it alone. At Stanford we met two other friends, all of us high school nerd buddies, who all had applied to the same colleges. Two ended up at Stanford, one at MIT, and myself and another guy at Cal Tech. At any rate, what made the concert musically special was that Lehrer was late, very late. Finally someone came on stage and delivered an hilarious monologue about why Lehrer was late. I had seen Lehrer before and knew he himself was speaking. Most folks didn't know this, which is why it worked when after the intro he went and sat down at the piano himself. Because he was late, Lehrer made up for it with an especially long and delightful concert. 
Hank Ballard and the Midnighters in a park in Springfield, Oregon. In the 80s. Although Ballard was my fav in high school, I'd never seen him perform before. What made this a special treat was that I went to the concert with a DJ who was interviewing him, so we got back stage, I got to meet him, sit in on a long taped interview, and so on. It was great to meet another hero, however belatedly. 
Doc Watson in a UCLA classroom. 1965. I was enrolled in a folklore course, and one of the benefits was that folk musicians came to class to perform. So I got to hear the legendary Doc Watson in a small room with 30 folks, an hour concert-and-Q&A session I'll never forget. 
Peggy Lee at the next bar stool. 1960. I was sitting at a bar in Monterey when the jazz festival was going on. Couldn't afford to go. Who should walk in and sit next to me but Peggy Lee! On the other side of her was the piano player. She sang a couple songs when I was close enough to touch her. 
Bruce "Utah" Phillips in the living room. My ex was close friends with Utah, having been in a bluegrass group with him. So when he was in town, he came by -- and I got to listen to another legendary folk artist up close and personal. 
The Kingston Trio at Cal Berkeley. I saw them in 1959, just before going into the Army. I was trying to figure out some Dave Guard banjo runs so made sure I got front row seats. I took notes through the concert on Guard's banjo arrangements, and near the end of the concert, one of them intro'd a song by saying, "For those of you taking notes...", which became a part of their comedy routine. I'm pretty sure I was the guy who inspired it originally.
Well, there are more but these come immediately to mind.
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