Robert Menes held a talk at the NYLUG a while ago about the Rockbox project:

I started out the talk by giving a little background on Rockbox; basically how it started, how it was ported around to new targets, and how the community grew as interest peaked. I showed off features of Rockbox, as well as supported targets, nearly supported targets, and even in-progress targets. I then went into describing Rockbox’s features in greater detail, and then a run-down of the development process, as well as how to compile your own builds. Many people asked questions along the way, so I answered them as they were asked. I also think that people were probably shocked at the sheer amount of targets that were shown off (nearly 40 DAPs were there!)

The 76 minute (1.6 GB) video from that event is available from the download.rockbox.org mirrors. Set your video player to stream from there unless you really want to download that entire thing!