Ooh, I had one of those in high school, saved up for months! I loved that thing - lots of space, it read song info from the files, supported playlists and had space for dozens of albums! DOZENS! Admittedly it ate 4 AA batteries in as many hours, but who cares? It was just as big as a discman, but SO MUCH MORE AWESOME. Used it every day on the school bus.

I kinda wanted an iPod when they came out, but as I grew up in a strict Dos & Windows home, that was out of the question.