I believe when you get the app you can subscribe for a free 30 day trial. Do that. Go to the radio section. Open up a radio channel on which ever artist you prefer. It really doesn't matter. When the songs start playing, tap the Right Trigger (RT) button. This skips to the next song. Keep doing this as fast as you can to hit 200 and than 1000. Should take 10-20 minutes. I found hitting RT for a while than hitting LT to go back to the previous songs was faster.