Seeing Phil Woods at the ShowBoat was right up there. I was already "impressed" before I ever heard him in a live setting though. I also saw both Phil Woods and Jim Hall on the same night at the Bottom Line in NYC. That was a great show, but the sound wasn't as good as the ShowBoat. The ShowBoat was one of the best venues I've ever been to for a small jazz group like that.
Oh yeah...seeing Miles in Boston was definitely a big night for me. To be honest though...and with no disrespect for Miles...I was more impressed by Mike Stern than I was by Miles that night.
Billy Taylor was another one. Awesome awesome piano playing. I had the pleasure of cooking dinner for him in my restaurant after the show, and chatted with him over a cup of coffee after dinner. A truly gracious gentleman he was...
Oh, most recently: Eddie Daniels. Playing the Thad Jones Mel Lewis Orchestra songbook with a local big band. "Three And One", playing the barisax part on clarinet, and so on. HUGE ! He also told us about those times, as he was the "newbie" in the orchestra, and Thad didn't want him to play clarinet.
Steve Lacy and the sextet playing at Johnathan Swifts club in cambridge on Halloween night around '79 or '80. In the middle of a rather dense group free improvisation he quoted Out of Nowhere. I've always loved that.
I've had the chance to see Jeff Coffin several times over the last 8-10 years in a few different settings and groups (Mu'tet, Bela Fleck, clinic, trio/ quartet before the mu'tet days...not with DMB yet though), and he kills it every time. In addition to being a great player, he has this energy on stage that carries through into his music...a must see in my opinion. He is also VERY approachable in the clinic setting and if you run into him when he's not performing. In the few times I've spoken with him, I am sure he would be an incredible educator...If he didn't always have the world tour thing going on.
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