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The two musicians who most clearly showed me how to improvise were Charles Mingus and his drummer, Danny Richmond. I listened specifically to what they were doing and realized quickly that they were LISTENING to each other and to the rest of the musicians, remembering what they heard and then playing what it lead them to play (say) in response. I heard each solo and within the solo heard what was played by the others. It was a conversation, not a monolog. Rather like... "When you said that, it reminded me of this." There is also an aspect of listening to myself and having the conversation develop from that, rather like thinking out loud.

I know this is not a technical explaination, but it has helped me enormously to understand that playing in jazz is as much about listening as it is about playing. This is true of blues as well. (I play harmonica)