iPod vs. Walkman
On the 30th birthday of the now legendary Sony Walkman, the BBC Magazine talked 13-year-old Scott Campbell into trading in his brand new iPod for a Walkman for a week to see what he thought. Spoiler alert: In head-to-head competition, the Walkman loses. But in fairness, this is partly due to Scott being completely unfamiliar with audio cassette technology.
It took me three days to figure out that there was another side to the tape. That was not the only naive mistake that I made; I mistook the metal/normal switch on the Walkman for a genre-specific equalizer, but later I discovered that it was in fact used to switch between two different types of cassette.