I know War flicks aren't everyone's forte but the "Band of Brothers" box set is fantastic. A bit pricy but worth it.

Some other of my favorites...
Lord Of The Rings (any and all)
Office Space
Tombstone
Quills

And an off the wall suggestion, but one I truly love: "The Complete Works Of William Shakespeare~ Abridged" by The Reduced Shakespeare Co. It is a 3 man troupe that makes a farce of the great bard's plays. Very funny. Can find it direct at http://www.reducedshakespeare.com/rsc_shop.html or can probably find it cheaper on Amazon.