
The film starts off with the narrator introducing many facts and legends about the American Old West outlaw, Jesse James (Pitt). Aside from Jesse, the film also tells the story of Robert Ford (Affleck), an insecure, unpopular young man who has grown up idolizing Jesse James. Bob seeks out his hero in the middle of a forest in Blue Cut, Missouri where the James gang is staging a train robbery. Bob makes petty attempts to join the gang with the help of his brother Charley (Sam Rockwell), who had been recently recruited. Jesse allows Bob to take part in the train robbery to try to prove himself, but Jesse’s brother Frank James (Sam Shepard) disagrees, saying that Bob hasn’t the ingredients to become a member in their gang. Gradually, Bob forms a love/hate relationship with Jesse, admiring him to the point of obsession while resenting his constant bullying. Bored with Bob’s fawning, Jesse eventually sends him away.
Months later, the gang members have gone their separate ways after their last train robbery. From this point on, Bob still wants to get involved in the gang as he starts to familiarize himself with the other recruits, who often stay at the farmhouse of Martha Bolton (Alison Elliott), the elder sister of the Ford siblings. Jesse’s cousin Wood Hite (Jeremy Renner) also stays there; he is attracted to Martha, but Dick Liddil (Paul Schneider), a charming womanizer, frequently gets in his way. During Dick and Wood’s stay in the latter’s home in Kentucky, Dick sleeps with Wood’s father’s wife, Sarah Hite (Kailin See). It is later related (while not seen) that Wood challenges Dick to a gunfight upon finding out, but it ends in a stalemate.
In exchange for a partnership, Dick reveals to Bob that he is in cahoots with Jim Cummins, an elusive gang member conspiring to capture Jesse for a bounty. Jesse visits Ed Miller (Garret Dillahunt), another former gang member, who unwittingly gives away information on Cummins’ plot. Thus, Jesse lures Ed deep into the woods and kills him, before going on a hunt for Jim. Jesse stops by Kansas City to bring Dick along for the hunt, and the two head to Bill Ford’s farm, where Jim usually stays. Bill is married to Jim’s sister, and is Bob and Charley’s paternal uncle. At the farm, Dick and Jesse are greeted by Albert Ford, Bill’s young son. Although Albert does not know where Jim is staying, Jesse brings the child to a barn nearby and violently beats him. Dick stops Jesse to prevent further harm to the boy. Confused and frightened, Jesse begins weeping and rides away to regather himself. Dick decides to travel back to Martha’s farm, and in doing so conveniently apologizes to the Fords for Jesse.
Wood returns from Kentucky to the Bolton farmhouse in a wintery morning. While Dick is still asleep upstairs with Bob and Charley, Wood retells his shooting scrape with Dick to Martha and Wilbur (another Ford brother) in the kitchen. When Wood discovers Dick is upstairs, he rushes up the staircase to the closed bedroom door, and Bob and Dick prepare themselves for the imminent gunfight. Wood kicks the door open, and the shooting begins. Charley jumps out of a window to dodge the gunfire, spraining his ankle, as Robert cowers in his bed. After a short gun battle, Bob shoots Wood in the back of the head, mortally wounding him. After Wood dies, the Fords dump his body in the woods nearby and hatch a plan to conceal this event from Jesse.
Jesse re-emerges one night to pay a visit to the Fords. During dinner, Jesse notices Bob’s anxiety and forces Bob to tell a story. Bob then reluctantly recites a long list of similarities he has with Jesse. Jesse is somewhat disturbed by this, and in return tells a story about once killing a man who held a grudge against him, explaining how Bob slightly reminds him of that man. Bob, now humiliated, throws a fit and miserably leaves the room, while Jesse and Charley plan a trip to St. Joseph, Missouri. At his home in St. Joseph, Jesse learns of Wood’s disappearance.
Bob begins to lose respect for Jesse as he realizes the nickel books about Jesse he had read during his childhood have little resemblance to the man he now knows. Consequently, Bob talks with Kansas City police commissioner Henry Craig (Michael Parks), saying that he has information regarding Jesse James’s whereabouts. To prove his allegiance with the James Gang, Bob urges Craig to arrest Dick Liddil, who has been staying at the Bolton farmhouse. Days after Dick’s arrest, Bob attends a party held by the Governor of Missouri, Thomas T. Crittenden (James Carville), celebrating Henry Craig’s efforts to finally rid Jackson County of the James Gang. To Bob’s surprise, Dick Liddil has been released from jail and is now meeting with the governor. It is revealed that authorities aren’t particularly interested in prosecuting Liddil; they’re really after Jesse James. To save himself, Liddil has disclosed information about the James Gang’s robberies in his confession. Afterward, Bob is brought into a meeting with the governor, and subsequently strikes up a deal with him. Bob is given 10 days to capture or assassinate Jesse James for a bounty of $10,000, and is given further instructions by Craig’s partner, Sheriff James Timberlake (Ted Levine). Meanwhile, on the way back from St. Joseph, Jesse talks to Charley about suicide. Charley then convinces Jesse to take Bob under his wing.
The brothers move in with Jesse to his home in St. Joseph, where they stay with Jesse’s wife Zee (Mary-Louise Parker) and their two children. One night in the living room, Jesse invites the Fords to take part in the robbery of the Platte City bank. He enacts the way he’ll cut the cashier’s throat, and demonstrates this by holding a knife to Bob’s neck. Convinced that Jesse will eventually kill them, Bob decides to kill him first. As a way to apologize for his actions, Jesse gives Bob a brand new pistol on April Fools’ Day, and tells him that he fears for his own sanity.
On the day of the assassination, Jesse goes out to retrieve the latest newspaper, which contains a story about Liddil’s arrest and confession. Terrified, Bob slips the front section of the newspaper under a shawl, then straps on his gun holster before sitting down in the kitchen for breakfast. Immediately, Jesse walks back to the sitting-room and discovers the hidden section of the newspaper, learning of Dick’s confession. Jesse glares at Bob, and asks why this matter hadn’t been reported to him. Panicked, Bob excuses himself and retreats to the sitting-room rocking chair, and Charley soon follows him to put on his holster. Jesse walks in to see if the two are ready for the trip to Platte City. After some silent contemplation, Jesse takes off his gun belt and lays it on the couch. Jesse sets up a chair under a dusty portrait and climbs on top of it with a feather duster in one hand. The Fords draw their guns, and Bob shoots Jesse in the back of the head, killing him instantly. When Zee tearfully questions Bob, he denies doing or knowing anything before Charley pulls him out of the house, declaring it an “accident”. The Fords run down to the telegraph office in order to wire the governor about the news. A brief montage then follows, describing what is to happen to the body of Jesse James.
After the assassination, the Fords become celebrities and end up in a theater show in Manhattan, re-enacting the assassination night after night with Bob playing himself, and Charley as Jesse James. Guilt-stricken, Charley attempts to write letters to Zee James, asking for her forgiveness, but would never actually send them. Overwhelmed with despair and terminally ill from tuberculosis, Charley commits suicide in May 1884.
After Charley’s death, Bob’s life takes a turn for the worse. He is openly shunned by the public and is branded a cowardly traitor, and threats from strangers are almost a daily occurrence. At times of anger, Bob dreams of visiting the families of Jesse James’s victims, hoping to convince himself that he killed Jesse for the benefit of humanity. Bob becomes an alcoholic, trapped in a constant struggle to liberate himself from his ever-growing guilt.
Ten years have passed since Jesse’s assassination. Bob has prospered over the past decade, and now acquires a steady income working as a saloonkeeper in the small mining town of Creede, Colorado. He becomes romantically involved with a dancer named Dorothy Evans (Zooey Deschanel), who would have long conversations with Bob in hopes of providing comfort to him. In the closing moments of the film, Bob is sought out and murdered by a man named Edward O’Kelley. At the same time, the narrator ends the film with an epilogue, recounting that O’Kelley would later be pardoned, and that in contrast to Jesse James, Robert Ford would achieve no fame after his death.
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