here's a thread about old MP3 players / personal stereos / walkmans / whatever the fuck you want to call them.
I think, roughly, in my lifetime I had:
• lots of cassette players including this amazing yellow one http://i.ebayimg.com/00/s/MTYwMFgxMDU5/z/XNQAAOxy63FS~q47/$_35.JPG (never an actual Sony Walkman)
• jumped straight from tape to MiniDisc, never had a DiscMan
• CREATIVE ZEN http://media.firebox.com/pic/p1006_column_grid_12.jpg
• obviously now I just use my phone cos I'm not a massive granddad
Never had an iPod Classic but I'd probably be sad if I did.