Get all the "Roaring Glory" shows. Some are not available on DVD, like the P-51 and B-17, but get them all.
I enjoy the "Warbirds over Wanaka" and "Flying Legends" airshow DVDs. You can order them from
http://www.aviation-worldwide.com/
I like Aviation Worldwide as they have a good international selection, as well as having NTSC movies in addition to PAL (remember PAL is the European standard, NTSC for North America). The Royal Navy Historic Flight film "Sea Fury" is one of my favorites (wonder why?), and they have it. Great footage, both historic and recent of the Sea Fury, as well as a cockpit checkout and in-flight view during an airshow display.
For drama I always come back to the same classics...12 O'Clock High and Battle of Britain, but also look at The War Lover, Piece of Cake, Bridges of Toko-Ri, The Right Stuff (the F-104 takeoff scene), Dark Blue World; just to name a few.
In the documentary catagory the color films "Memphis Belle" (the original one filmed during the war), and the British version "Target for Tonight" can't be beat.