The Assassination of Jesse James by the Coward Robert Ford (2007)

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Meticulously crafted portrait of one of 19th century America's most charismatic figures. While Jesse James and his brother Frank hold up trains to strike back at the Union that ruined their lives, 19-year-old social misfit Bob Ford slowly worms his way into the inner circle of the notorious James Gang. Bob's infatuation gradually festers into jealousy and hatred, and when lawmen put a bounty on Jesse's head, Bob agrees to pull the trigger. Aided by his brother Charley, Bob bides his time, waiting for the perfect moment to strike.