It started a couple months ago with a song I purchased on iTunes years ago. I hooked my iPod up to a car to play music and it wouldn't play - it said it was playing, but it was completely silent. It was the only song to do tha, but it worked with headphones. Now it won't play on headphones or out loud. Also, another song (purchased a long time ago) is doing something similar. It plays normally for a couple of minutes, then skips around, starts at the beginning (still a couple minutes 'into' the song) and then goes silent until the end, where it starts over. Same with of without headphones. I don't know yet if other songs are doing this too, but this song normally plays properly. It played normally even after the last time I connected to the pc, so I know it isn't that.