Che (2008)

Two films about Che Guevara (Benicio Del Toro). One film about the successful revolution in Cuba, the other about the less than successful revolution in Bolivia.

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While attempting to overthrow the government of Bolivia, Ernesto "Che" Guevara stuck religiously to the playbook of the Cuban Revolution. This lead directly to his execution on October 9, 1967. They say that the definition of insanity is doing the same thing over and over again expecting different results. Yet is it not equally insane to do the same thing and expect the same results. By it's very definition, Revolution changes everything. Not just the country in question, but the world around it. After Cuba fell, the Capitalist world was on watch. Che didn't stand a chance. 

After the revolutionary hit that was Sex, Lies and Videotape, Steven Soderbergh spent the better part of the 90s making commendable flops. The world had changed, yet he remained the same. Eventually he learned the delicate art of playing the Hollywood game while still holding true to his own muse, but I think those years adrift really stuck with him. Aside from the late Orson Welles, I cannot think of a filmmaker better suited to bring this tale of failed ambition to the screen.