Sorry if the question was a bit succinct. I'll rephrase it. If Itransfer say 200 tunes to my memory stick, plug it into a USB port, will it, after it has played the200 tunes stop? Or will it return to the beginning and keep replaying them? hence the tunes would be on a LOOP.
Your medial player (presumably iTunes) will play the tracks in exactly the same way it plays your other tracks. The memory stick is just treated as another drive.