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According to a pre-production news item in Hollywood Reporter, Arleen Whalen was to play the female lead in this film. A October 14, 1938 news item in Hollywood Reporter notes that director Henry King was confined to bed because of a swelling of his inner ear. Irving Cummings replaced King until he returned to the set on 24 Oct. According to materials contained in the Twentieth Century-Fox Produced Scripts Collection at the UCLA Theater Arts Library, Darryl Zanuck suggested that the desire for revenge for the railroad's murder of his mother should motivate "Jesse" to become a renegade. The real Jesse James was not the handsome romantic figure portrayed by Tyrone Power, but a cold, ruthless killer. Jesse was born in Missouri in 1847, and at age fifteen, joined a group of vicious, pro-Confederate guerrillas led by William C. Quantrill. After the Civil War, Jesse, his brother Frank and several other men formed an outlaw gang and began robbing banks, stagecoaches and trains. As depicted in the film, in 1876, the gang was almost wiped out during a bank holdup in Northfield, MN. Jesse and Frank escaped and formed a new gang. On April 3, 1882, Jesse was shot and killed by fellow gang member Bob Ford for a reward. Six months after Jesse's death, Frank surrended and was tried and acquitted twice.
An article in Life notes that the film was shot on location at Pineville, MO, and cost $1,600,000 to produce. Materials contained in the Twentieth Century-Fox Records of the Legal Department at the UCLA Theater Arts Library add that during the execution of a stunt, a horse, ridden by stuntman Cliff Lyons, drowned after jumping off a cliff into Lake of the Ozarks at Bagnall Dam, MO. The crew attested that the horse did not suffer any injuries in the fall, but became excited when he hit the water and drowned before the crew could get a rope around his neck. Because of the incident, the regulation of motion picture production by the American Humane Association became part of the MPPDA code. Modern sources note that Jo Francis James, who is credited with assemblage of historical data, was Jesse's granddaughter. In 1940, Fox released The Return of Frank James, a sequel to this film (see below) in which Henry Fonda reprised his role as Frank James. Among other films based on the life of Jesse James was the Paramount 1950 film The Great Missouri Raid, directed by Gordon Douglas and starring Wendell Corey and Macdonald Carey; the 1972 Universal film The Great Northfield Minnesota Raid, directed by Philip Kaufman and starring Cliff Robertson and Robert Duvall and the 1980 film The Long Riders directed by Walter Hill and starring Stacy and James Keach as the James brothers.