Here list a few sites where you can download free movies; they are all free, all legal, and feature hundreds of high-quality movie clips and full-length movies.
After download, you can convert movies to ipod, or transfer movies to iphone, put movies to zune. One thing you have to remember: convert movies to the certain format first.

Popular video websites:
YouTube: you can upload, watch, and search free videos here.
Google Video Search: Find videos, movies, and TV programs online.
MySpace Videos: MySpace has one of the largest video collections on the Web.
Yahoo Search-Video. Search for videos and movies on the Web. Also includes a link to submitting your own video to Yahoo to be indexed.
Veoh: thousands of free videos available here.
Hollywood.com: Trailers, movie clips, and more.
VideoBomb: "Video Bomb filters up the hottest videos on the internet: people submit links to the 'Incoming!' page and you bomb the best ones. If a video gets a lot of bombs quickly, it makes it to the front page."
The Open Video Project: a shared digital video collection
All Movie Guide: Comprehensive database of film synopses and reviews as well as concise actor biographies.
Cinema Now Free Videos and Movies: Usually this is a pay-per-view site, but they've started putting up freebies.
Gotuit: tons of high-quality videos here.

and the other links:
www.cnn.com/video/
www.bebo.com - (Video, Music Video and MP3)
www.metacafe.com
www.dailymotion.com
www.blip.tv
www.revver.com
www.archive.org
www.break.com
www.tv.com
www.pavtube.com
www.broadcaster.com
www.livevideo.com
www.spikedhumor.com
www.vidmax.com
www.savvy.com
www.glumbert.com
www.vidilife.com
www.pyzam.com
www.funnyjunk.com
www.totallycrap.com
www.vidiac.com
www.fhm.com
www.weakgame.com

More about these: Free Movies Websites (http://www.pavtube.com/free_resources/free_ipod_video_sites.html)

thepiratebay.org

Yeah...i use the piratebay to download movies and i use movies-on-demand.tv to watch them.