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Nice matchup, "The Killing" is a great early Kubrick, but "Dr Strangelove" is the best satire ever made.
I just had myself a Kubrick double feature and watched both of these for the first time. While I enjoyed Dr. Strangelove, I liked The Killing slightly more. Although the performances were much better in Strangelove, I prefer heist films to political satire.
I enjoyed "Strangelove" but felt like it fell a little flatter than expected at times. Maybe it was all the hype I had heard beforehand. "The Killing," on the other hand, was a lot of fun, more fun than I knew Kubrick could have, and it inspired so many of my favorites today.