Music is more popular than it’s ever been, but the models for distributing and promoting it have changed radically. Fans are getting huge amounts of music directly from the web (legally and illegally), artists are becoming stars without ever having to deal with the labels, and entirely new platforms, from ringtones to videogames, are helping to turn songs into hits.

Below, we chart this evolution through actual songs. Each of the following 10 tunes captures a key chapter in the rise of digital music, from the song that sold the most ringtones, to a cut from the first record to be released exclusively online, to an early and influential “mashup.” Meanwhile, as the digital revolution marches on, there will continue to be new songs that shape the future of the business. And maybe even a few old songs—this could be the year that the Beatles finally get online.

—Peter Newcomb