I'm hoping y'all can help me; this has frustrated me to the point of tears, and I can't seem to find any solutions or even allusions to this problem online. I have three seasons of a TV show. They're in m4v format--all three seasons were purchased directly through the iTunes store a little over a year ago, and they were working fine on my father's 3rd(? I think; it's video-capable, at least) gen 80gb classic iPod until recently. I synced his iPod for him this afternoon, and they've just stopped working. For the life of me, I cannot get them to play properly on the iPod. I can get audio, but no video. The iPod seems to be treating it as an audio-only track. I suspect the problem is that they are stuck as Music in iTunes rather than a TV Show, but iTunes won't let me change the media kind to TV Show! If I select a single episode and go to Get Info -> Options, the only Media Kinds I can choose from are Music, Podcast, iTunes U, Audiobook, and Voice Memo. All the video options and metadata (other than that) are still editable no problem. screencap: http://i152.photobucket.com/albums/s178/lquark/untitled-6.jpg But if I select multiple episodes, the option to change it to TV Show and Movie and all the other video formats becomes available. screencap: http://i152.photobucket.com/albums/s178/lquark/untitledone.jpg If only it was that easy. Even if I click TV Show, it won't actually change anything. The episodes still stay listed as Music and won't play on the iPod. The only thing I can change them to with any effect are the audio-only types: podcasts, music, etc. The thing that really frustrates me is that the episodes play in iTunes just fine! Even though they're listed as music and not TV Shows, I just double-click and they start right up; both video and audio run, no problem. They play whether they're listed as music, podcasts, audiobooks, or whatever. It's just in the transfer to the iPod that they seem to hit some kind of disconnect. If you have any idea how I can get these (iTunes-purchased!) episodes to play on the iPod, I'd be eternally grateful. Oh, and if it matters, it's iTunes 9.0.2, and he's running Windows XP.