I've often wondered if my ride would be more enjoyable with music. When I was riding the STP last month, a few people had seatpack radios and one group even had a team member towing a Bob trailer in which sat a homemade boombox crafted from car stereo parts. He had a wired remote which I think possibly led to an MP3 player... with a lot of storage because I never heard the same song twice all the way down to Portland (admittedly I broke contact with him a few times). Needless to say, he gathered quite a following and at least a couple of dozen riders were pacing him just to get some music.
On another note (no pun intended), what are people's opinions on FRS radios with a single earbud for communicating with other riders in your group? Have you used them? Did the VOX circuitry work effectively? I know racers use similar radios but I suspect they're also higher quality/more expensive than the ones in blister-packs you now see at the grocery market checkout lines. I just picked up a two-pack Audiovox FR-530 for $12 at Staples. I need to get a set of earbuds for them though. BTW, I believe some of these units even have built-in FM radios. I think some of the Motorolas do... along with NOAA weather.
Later on, I plan on getting a Garmin Rino 120 when it hits the market. It would be nice to download a route map to it and combine it along with comunications for my group rides. Plus if someone else has a Rino, beaming each other position information along a route or trail can be helpful when the group gets strung out.