The Chairman's Award is judged primarily on the written essay and the interview/presentation at the event; IIRC, the video is required for submission, but not necessarily viewed. One thing to remember: If you're a NASA Grant recipient, (and my memory is correct) having a Chairman's submission is required. (It also helps your case for Rookie All-Star.)
Rookie All-Star has no required submissions. However, having things like a Chairman's Award essay can help you out tremendously.
In addition to Richard's links, you may want to read
http://usfirst.org/sites/default/fil.../06_Awards.pdf It's Section 6 of the Administrative Manual, and has the complete list of information on all the awards. Pay special attention to sections 6.2 (all awards and short descriptions) and 6.4 (Chairman's Award).
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Past teams:
2003-2007: FRC0330 BeachBots
2008: FRC1135 Shmoebotics
2012: FRC4046 Schroedinger's Dragons
"Rockets are tricky..."--Elon Musk
