4. MPMan (1998)
MP3s completely changed the way we listen to music, and literally forced the industry to change the way they marketed and distributed albums. One of the things that solidified that fate was the creation of the MPMan. Looking back now, the specs are pretty laughable — it could only hold between 35 to 90 minutes of music depending on the model — but it was pretty revolutionary at a point when digital music literally was being born. The MP3 encoding process made the MPMan the most difficult music player ever, but it was the first steps to where we are today.