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There's no fighting in the war room vs. Of course they're trying to kill you boy this is WAR!
I'm sure many would go with Dr. Strangelove... it is Kubrick after all. But, I actually think Catch-22 is a superior film. I can't quite express why, I just find the humour in Catch-22 to be unique, even among Black comedies. Dr. Strangelove's humour seems normal for black comedies, just done to perfection. Both great movies though.
For films, clearly it's Dr. Strangelove ... but Dr. Strangelove cannot compare to Heller's original. In fact no film at all, even The Godfather or Citizen Kane, can compare to it. If I made a list of greatest works of the 20th century chances are not a single film will make the top 10. Books just have more room to go into depth about complex themes and ideas.