actually you should be able to change the order (I can with ipod touch and could with classic I had before that). If you put oldest first, then it will move to then next one. when it's newest first, then it stops. I have only ever been an iPod person. I started with iPod Color. after about 3 years it quit updating, couldn't put anything on it. It erased itself when i tried to restore, and would not sync anything, and I bought a refurbished classic. after that I upgraded to 4th gen ipod touch. I have a ton of music and musical tastes. probably don't need it all with me, but I always buy the largest I can because in short time I approach full.