Yeah, now that you mention it that was about the time when movies started to become monumentally cookie-cutter and the Sopranos kinda kicked off the new generation of awesome television. There have been some good movies since then, don't get me wrong, but I can't honestly say very many of them have been new or creative in several years. Some, but not very many at all.
Video games are kinda going through the same phase right now, too, it feels like. It's depressing, but it actually makes sense that it turned out this way, at least for video games. The cost of production on a AAA game is so high that there is almost no room for taking risks. It's not really the developers' fault so much as it is consumer demand mixed with the nature of a capitalist economy. A depressing vicious cycle. I'm not too versed on the movie business, but I would imagine it's grown stale for about the same reason.
But hopefully we'll get past this particular barrier; at least with video games when the technology stops advancing and it gets cheaper and easier to make the same level of quality I think we should start seeing more diverse AAA titles again. Who knows when that'll be or if it'll ever happen for movies. Not really sure what the roadblock is for movies, anyway, but I don't see why it would be technology. It really seems like it's already reached a plateau of that kind to me. Then again, like I said, I know next to nothing about film making, which is why I'm having to draw parallels with video games in the first place heh.