Here's what happens when you give a 13-year-old from 2009 a Sony Walkman—the tape kind—and ask him to figure it out without any outside help: incredible confusion.
To the kid's credit, he was able to deduce that the tape had two sides (took him three days) and that you could switch between two kinds of tapes fairly easily. He was also given weird looks on the street and allowed to listen to music in class because of his teachers' nostalgia. Other choice quotes:
Another notable feature that the iPod has and the Walkman doesn't is "shuffle", where the player selects random tracks to play. Its a function that, on the face of it, the Walkman lacks. But I managed to create an impromptu shuffle feature simply by holding down "rewind" and releasing it randomly - effective, if a little laboured.
I told my dad about my clever idea. His words of warning brought home the difference between the portable music players of today, which don't have moving parts, and the mechanical playback of old. In his words, "Walkmans eat tapes". So my clumsy clicking could have ended up ruining my favourite tape, leaving me music-less for the rest of the day.
Another useful feature is the power socket on the side, so that you can plug the Walkman into the wall when you're not on the move. But given the dreadful battery life, I guess this was an outright necessity rather than an extra function.