Not in order - I'd watch any of them in the first two categories if on:
Best:
12 o' Clock High
The Battle of Britain
The Great Escape (it's a stretch but since they were Allied airmen, I'm counting it. Marvelous book as well.)
Honorable Mentions:
The Bridges at Toko-ri
The Dambusters
Airplane! (The comedy. I believe folks are writing "Airplane" when they mean "Airport")
Worst:
Any Iron Eagle (only saw the first, but imagine the sequels just get worse)
Never saw/never will:
Pearl Harbor