Pretzel found his old Rio player digging through boxes after a move and "cammed" it. He was surprised to remember it had a parallel cable that attached to the computer, for transferring these new mp3 things to and from the player. He found a website from the late '90s showing how to keep your transfer software up to date after the whole world moved on.
Not nearly as old but just as archaic is this Samsung mp3 player that I was half-seriously thinking about using as a retail package for my entire musical production (about 200 songs in late 2006). A friend joked that it would be like the dedicated U2 iPod. Nowadays if you search for "Samsung mp3 player" they are selling something that looks like a phone, with a display screen instead of this large speaker grille (and no folding design). Presumably this is because speaker technology has improved and little phones now make big booms. Also because everything needs to look like a phone.