1. Orde Wingate
Likely the most obscure entry on this list, Orde Wingate was one of the founders of the modern style of guerilla combat who was considered by many of his peers to be insane. Wingate established guerilla units in many theaters of World War Two but is probably best remembered for forming the Chindits during the Burma campaign in the Pacific theater. The effectiveness of the Chindits has become a slightly controversial part of history with some saying that they were more useful as a propaganda weapon than as a viable fighting force while others saying that they helped the allied military with several innovations such as supplying military units cut off by enemy forces. Wingate was by most accounts an extremely eccentric individual who would sometimes pass out orders while in the shower and Churchill, upon meeting him, realized he was a little too crazy for any kind of higher up leadership position. An adaption of Wingate's life would help show the vast scope of World War Two and put a unique twist on it by showing it through the point of view of someone who was likely insane.
Casting Choice: Jim Carrey would be a good choice for playing an eccentric if he wasn't too over the top but I think the best pick would be Sam Rockwell since he's had a history of playing slightly oddball characters.
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