Hmmm then maybe the Ipod is the way to go. It's very good (I'm talking about the nano here) and so there is a great deal of industry buzz. Plus, it can get something of a historical context. About 10 (maybe it was 11 or 12 by now) years ago, Sony Walkmen came out, and that really changed personal interactions, in that sometimes you just saw people bopping on the street for what looked like no apparent reason. And when people waited in line, they could (and did) have music, whereas we hadn't before that.
I think the original Ipod kind of brought that dichotomy back, kind of the techno haves and have-nots. Never mind that many people spend their time yakking on their cel phones all day long; this is even less human interaction. And with a teeny tiny device, you could bring it into practically anywhere and no one would be the wiser. Do people wear them to church? School? Work? There is a social component -- or rather an avoidance of society component -- that seems to go along with smaller and less conspicuous personal entertainment devices.
PS Welcome to able2know.