Scott Rosenberg's excellent notes from Web 2.0 include a bit about the Grateful Dead.
Mickey Hart was on stage at the end of the day Thursday, talking about the history of the Dead and the "tapers" the band allowed to record their shows. He pointed out ways in which that community was similar to today's file-trading hordes, and ways that it was different. But one thing he said stood out for me: The Dead played for pay and they played for free; "we always played better when we played free."
This reminded me of a brief chat I had with GD drummer Bill Kruetzmann at CES. It took me a while to find the reference; forgot I'd done it as a caption on Flickr. (The camera-phone photo predates my understanding of the zoom feature, unfortunately; Bill Walton actually looks small.) I asked him about music swapping since the Dead essentially were p2p pioneers. He mentioned the tension between making money and free music but said, "Music needs to be free." I wrote then and still think now that the GD have managed to do both by respecting their audience.