Yesterday I managed to get something called ppstream running. It is like kazaa/emule for Chinese videos. It is really cool and I definitely recommend it! It has lots of Chinese video content. It also has English movies with Chinese subtitles. I found things like the new Karate Kid movie, Salt, Smallville, Project Runway, Yip Man 2 (cantonese), fei cheng wu rao (the Chinese dating show).
PPTV is a similar program. I tried that first but it caused my internet connection to stutter (probably opens too many sockets or something).
To get ppstream running I used the tutorial with screenshots here:
http://dolores.pinoyexchange.com/forums/showthread.php?t=452878
I am still trying to figure out getting these videos to my tv using my xbox. This should be possible using Windows Media Player. Right now everything is played through ppstream's internal player though so I can only watch from my computer.
As to legality and copyright and such, check your conscious :-)