Yeah I had an iriver. That thing was great because it essentially acted as a giant (for the time) USB drive. And it could play any mp3s and you put on it.

You synced music by manually managing folders on the device. All my non technical friends were horrified by it. They didn’t have neatly organised mp3 libraries. For all of iTunes’ problems, being able to plug in a cable and hit the big “Sync” button was really simple and convenient.