Two that might have slipped under the radar:
1. Everything is Illuminated is a very good film--quirky, funny, touching, and appealing to anyone who knows what it is like to try to hold on to the past. I suspect the historians in the room might be especially attracted to it. (JD it's a must-see for you.) Plus Boris Leskin, who plays the grandfather, gives the best supporting actor performance I've seen in a while.
2. For anyone who has ever worked in the food service industry (restaurants), Waiting... is a classic. It's not exactly high art--think of it as Office Space crossed with Super Troopers, in an Applebee's--but Ryan Reynolds alone is worth the price of admission. Warning: If you are offended by anything at all, do not see this movie.