I've written a plugin for Winamp that allows users to stream Grateful Dead shows from archive.org's enormous collection of user-uploaded audience and soundboard recordings.
It randomly chooses a show, streams it, and when it's done, randomly chooses another. I wrote this for myself to listen to the Dead at work, but I figured I'd spread the joy.
If you have the latest version of Winamp, you can download my plugin here.http://www.winamp.com/plugin/deadhead/222488
If you don't
have the latest version of Winamp, you can download it free here.http://www.winamp.com/