Alternate Character Interpretation: The film strongly implies that Jesse James realized that the Ford boys were about to kill him and willingly went to his death, apparently out of simple weariness.
Award Snub: While the film made a number of critical top ten lists, it was nominated only for Best Supporting Actor and Cinematography, winning neither. Special mention must go to Nick Cave and Warren Ellis' beautiful score which didn't make the list of nominees.
Critical Dissonance: The film earned positive reviews and made quite a few top ten lists for the year, but it flopped at the box office and make back half of its thirty million budget.
Ending Fatigue: The title event occurs about two hours into the film, but the film continues for more than a half hour, tracing the Ford brothers' lives for years after the event. Some viewers felt that the film should have wrapped up quickly after the murder, apparently failing to realize that Robert Ford is just as much a main character as Jesse James. A rumored director's cut that has yet to see the light of day supposedly continues for a full two hours after the murder.
He Really Can Act: Brad Pitt has proven he’s a capable dramatic actor as well as comedic, but his role as Jesse James may be his best one yet, as he seamlessly goes from a charismatic, yet dangerous outlaw, a caring family man, to a paranoid, murderous man that still believably displays vulnerability and fear over his impending mortality over the course of the film. Casey Affleck both sells Robert Ford’s shy, quiet demeanour and need for validation, his growing resentment and disillusionment with both his life and Jesse, to his simultaneous determined, tearful reaction to murdering Jesse, and his guilt, anger and regret of her actions in the final quarter of the movie, just through his facial expressions alone.
It Was His Sled: Jesse James is going to be assassinated. By Robert Ford. It's left to the viewer to figure if Ford was a coward for what he done.
Jerkass: Wood Hite and Charley for their merciless bullying of Bob. Jesse also qualifies
Jerkass Woobie: Both Jesse James and Robert Ford. Jesse is a murderous bully and Ford is a sniveling snake-in-the-grass, yet both are so beat up by their problems that you can't help but feel for them.
Jesse breaking down and crying after completely snapping and beating on a child.** The final narration describing Bob's fate.
What Could Have Been: The role of Robert Ford was down to a choice between Casey Affleck and Shia Lebouf. The executives chose Casey because they thought Shia was too young.