Just got the new 16GB iPhone 3G (yay) and wanted to take advantage of the extra storage over my previous iPhone and iPod models. Originally I had iTunes set to automatically sync new and unwatched TV shows to my iPod and iPhone, and that worked flawlessly. Now that summer is here, I am not getting any new episodes until the new seasons start. Bummer. I have all this extra space wasting away on my new phone! There SHOULD be a way to "syndicate" or "rerun" shows if new shows aren't available, but after countless attempts of trying to create dozens of Smart Playlists that reference each other in a web of utter confusion, I am turning for some help. What I would like to do is this: If Show A contains unwatched episodes sync least recent unwatched episode of Show A Else sync least recent watched/random episode of Show A This way I never "run out" of content to watch. Could this be done with AppleScript?