Gaelic Storm as a whole, and especially Patrick Murphy, are just incredible with their fans. My wife talked with him at a concert in a S.F. bar early on in their career and he couldn’t stop blessing the fans. When we were finally able to see them again years later, he apologized for being so booked in the midwest they couldn’t come out to the Bay Area since then.
I haven’t been able to buy them some pints yet, but they are scheduled to return to S.F. (finally) in October. Yay. 
I met Charlton Heston at an event and he seemed really cool and willing to talk for a bit.
The Bare Naked Ladies put on a good show and I watched them come out and bring people not only to cheer for the opening act, but their lead singer also led a conga line to a side act that was opening on a separate stage before the opening act.
The Grateful Dead lived by their fans, and I assume Jimmy Buffet is the same (the Parrot Heads are too important for him NOT to love them).
I’ve seen him acoustic three times, and with his band the last time, and he does it with his band also. And I have a bootleg of a concert in Italy where he was joking with the audience too. I knew nothing about him the first time I saw him, and became a fan immediately.
I saw them once in Princeton, and once on Broadway. In Princeton Penn came out during intermission, and encourage skepticism, and even mentioned the Skeptical Inquirer. Teller dd not show.
FWIW, my brother attended a small, low-key concert that Jimmy Buffett held on the beach of an island in the Lesser Antilles (for the life of me I can’t remember which island…I think it was Antigua), and talked about how Buffett was hanging out with fans after the show, just relaxing and having a good time on the beach. I can understand if he’s stymied by the more obsessive Parrotheads (kinda like Shatner with the uber-Trekkies), but he seems like a pretty decent guy overall. Anyone who writes a lot of songs following the theme of “to hell with this, I’m going sailing” can’t be all that bad 
I can’t believe no one has mentioned the ultimate interacter with his audience: Bruce Springsteen. No one works harder to give fans a good time than the Boss.
I agree about James Taylor. I’ve seen him in concert many times, and he just seems to love what he does. he even wrote in his song “That’s Why I’m Here” :
Here’s to the people coming back every year,
got your baby, got your blanket, got your bucket of beer.
I break into a grin from ear to ear,
and suddenly it’s perfectly clear.
That’s why I’m here.
My sisters went to see Harry Chapin several times before he died. He loved to play. One concert, they were kicked out of the hall because they needed to shut down, and he kept playing in the parking lot. He loved to perform and loved his audience.
StG
I just got back from Shine a Light the rolling stones/martin scorsese flick, and it was good:
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The boys still bring it.
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They looked like they were loving every minute of it
The Isleys grew up with my Boss, and Rudolph Isley has been in my office a few times with his wife. He was very very personable, particularly when I asked him about touring with the Beatles in the early 60’s and having them record “Twist and Shout,” which the Isleys wrote (and he was amazed that I knew this fact). He enjoyed the conversation about his “early days.”
When Heston, the guys at digitalbits.com (the best DVD review site) wrote about the time they met Heston and how he basically put on a mini one man show for all of the writers who were completely in awe of him.
Chris Isaak and his band are very good at this too. I’ve only seen them once (though my sister is a huge fan) and they all came out, did autographs and mingled for a good hour after the show. Chris stayed behind a U-shaped table set up, but signed for everyone and chatted for a few seconds with us all.
The rest of the guys were out in the corwd and I actually got talk for a few minutes with two of them.