[rchaud]

iTunes is certainly awful to use, but the interesting part of that story is not iTunes itself, but the work and negotiation that had to happen to license music from all the major labels to populate the iTunes marketplace. Sony had a huge first-mover advantage in that space (their own global music label, movie studio, video game console AND the Walkman brand), but was too busy forcing its disparate businesses to compete against each other.

The end result being that they completely missed the boat on the then-nascent digital music market, and less than 15 years later, have spun off most of those brands and hardware-wise, Playstation aside, are limited to making (very nice) camera sensors for iPhones.