The history of iTunes is full of excitement, disappointment, and even some controversy that all began in 2001. Now at that time, the iPod didn’t exist and playing music from CDs was standard. There were MP3 players, but the industry was still in its infancy and wouldn’t explode until a few years after the iPod was released. Most computers were capable of importing songs from CDs and this created a problem with managing those song files effectively.

The most popular desktop music managers were Real Jukebox, Windows Media Player, and Music Match. The problem with these applications was that they were not only unappealing and complicated, but they throttled things like encode quality and CD burning speed to encourage users to pay for the software’s pro version. Apple capitalized on these shortcomings by introducing a free, simple, and powerful digital music jukebox called iTunes.