In the late 1880s Milford Farnsworth is the inept door-to-door insurance salesman for the Plymouth Rock Insurance Company of New York who unwittingly sells a $100,000 policy to Jesse James while he’s visiting a bar in NYC. The company president, Titus Queasley, sends Milford with the cash to Jesse’s hometown of Angels Rest, Missouri, to get him to cancel the policy on the high-risk client before his death breaks the company and if he doesn’t get Jesse to cancel the policy to act as his protector so he doesn’t die and thereby his saloon singer girlfriend, at the Dirty Dog Saloon, Cora Lee Collins, his beneficiary, won’t be able to collect.
Jesse James robs Milford on the train of the $100,000 and eventually decides to kill him after dressing him up in his same outfit so he looks like him. This way the real Jesse plans to marry Cora and collect on the policy after burying Milford in Boot Hill, who will be mistaken by the insurance people for Jesse James. It concludes with Milford running away with Jesse’s beautiful redheaded would-be bride Cora (somehow she falls for Milford) and when he misses his train, he gets into a gun duel with the James Gang in town. —Ozu’s World of Movie reviews