TV Shows and Music purchased through iTunes doesn't work on my iPhone

When I play some of the music and tv shows purchased through iTunes on my iPhone, it would play for around 30 seconds for music and anywhere from 5-20 min for the shows, and then either go to the next song, or stop playing the video for no reason.
It seems to be a specific spot which "crashes" the song, because say the song or video stops at 2:31, I can seek to "2:33", and the song/video would play normally, and not crash.
What's the reason for this?

Contact Apple and report a problem via your *purchase history*. Either from the iTunes store, or the email receipt they send.
Also you might have more luck in the iPhone forums:
http://discussions.apple.com/category.jspa?categoryID=201

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