I was experiencing the same problem. I manually manage music & videos on my iPhone, so I had to re-load them after upgrading from 1.1.4 to 2.0. I'll confess that I was one of the "early adopters", who downloaded the 3G software the day before the additional 2.0 release. Here's what happened to me:
After reloading my songs and videos which were blown away by the upgrade (expected, no complaints there), everything was fine and they played perfectly -- as they had with 2.0.
On Friday, I read that the 2.0 software that I'd loaded was actually only for the 3G phone, not iPhone 1.0 -- so I did a "restore" using the firmware that I was supposed to have used all along.
This morning, NONE of the 10+ movies that I'd had on my iPhone will load to the phone; iTunes insists that they weren't copied because they were "not playable on this iPhone." I disconnected and went about my business. However, just now, I plugged my phone back in to get the exact text of the error message -- and found that the movies are now transferring just fine.
So there's something odd going on. Alas, I don't know what.