It's kind of a trick question. The longest movie to win a Best Picture Oscar is "Gone with the Wind" (1939) at 238 minutes (3 hours and 58 minutes). A documentary about OJ Simpson and the movie 'War and Peace' both won Academy Awards and were much longer tham GWTW, but neither won for best picture. GWTW still holds that record.
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No idea which movie was the longest. DGAS. I'd be set back a year in an Introduction to Hollywood class. DGAS. As far as Hollywood goes my intellect tops out at the Animal House, Blazing Saddles, and Caddy Shack level.
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