American Outlaws is a 2001 Western film directed by Les Mayfield and starring Colin Farrell, Scott Caan, and Ali Larter.
The southern army is trying to track down the Yankee army during the civil war. The south is ambushed, but thanks to the sharp-shooting of Frank James (Gabriel Macht) and the distracting and at the same time clever antics of Jesse James (Collin Farrell), the south manages to pull through. The James brothers, along with their war buddies, the Younger brothers, congratulate themselves, but (during the ride to reconnect with their unit) are surprised to learn that their army has pulled out, General Lee had surrendered the previous day at Appomattox, and the war is over. The group decides to return home to their families and farms.
Things have changed when they get back to Missouri. The town is occupied by the Yankee army, Jesse's childhood friend, Zee (Ali Larter), has grown up into a very attractive young woman, and there is a man hanging in the town square, ostensibly for treason against the North.
In actuality, those farmers with large amounts of land are being pressured to sell their farms to the railroad company, who are pushing across North America. If they don't sell their land to the well-groomed, suit-wearing Thaddeus Rains, (Harris Yulin) and his secret-service organizer, Allan Pinkerton (Timothy Dalton) the farmers are burned out of their homes, or killed outright.
Frank James finds that the railroad doesn't even need their land -- they're just buying it as cheap as they can get, to push the railroad through. The James and Younger brothers don't want to sell, and Cole Younger (Scott Caan) loses his temper when several 'railroad men' approach him about selling, and kills two of them. The army decides to hang him (since they were working for the government, he faces charges of treason), but his brothers Bob (Will McCormack) and Jim Younger (Gregory Smith), along with Jesse James and Frank James, decide to rescue him, with some help from Zee. During the rescue, Jesse is shot in the shoulder, and has to hide out at Zee's farm.
A few weeks later, when Jesse has recovered, the railroad sets fire to the James' home, killing Jesse and Frank's mother (Kathy Bates). The James and Younger brothers ride out for revenge against the railroad men -- but instead focus on the bank's payroll, reasoning that 'you could kill a hundred railroad men and they won't care', but if they steal the payroll and attack supply trains, the army will sit up and take notice.
Dubbing themselves the 'James-Younger' gang, they set out robbing banks, with Pinkerton and Rains struggling to stop them. The impact of the James gang is only increased when they commit the first daylight bank-robbery in history, turning themselves into folk heroes in the process.
Eventually, the gang comes to blows over leadership, with Cole Younger feeling that Jesse is getting an overblown ego from the publicity of 'his' gang's activities. Jesse backs down, after a bitter argument, and lets Cole plan and execute a robbery; Cole's chosen target proves to be a trap set by Pinkerton and Rains. Jim Younger is shot and killed, and Jesse and his brother (who are tired of the killing and fighting) leave the gang, with Jesse later marrying Zee.
The gang doesn't do as well without the James brothers. People don't respect the Younger brothers as much as they did the James-Younger Gang, preferring Jesse's easy-going 'nice guy' personality and his warm, friendly and accommodating manner, which had won the affection of the townsfolk in previous robberies.
When Jesse and Zee attempt to start a new life, Pinkerton finds and arrests Jesse. During the train ride to the jail, Jesse is chained in a rear car, but manages to trick one of the deputies into showing his gun, which he uses to escape to the top of the train car.
Meanwhile, Zee and the remainder of the Gang shoot a cannon at the locomotive, stopping the train and rescuing Jesse. Confronted in the final moments by the two men he's come to hate, Jesse shoots neither Rains nor Pinkerton, but rather Rains' prized watch, a treasured gift from his father.
Pinkerton tells Jesse, through gritted teeth, that he should go to Tennessee, as 'the railroad has no interest in Tennessee', and therefore, neither does Pinkerton (since Pinkerton's being paid by the railroad).
