The first two movies were "Jesse James Under the Black Flag" (1921) and Jesse James as the Outlaw" (1927). Both featured Jesse James Jr. as his father. Two more, "Jesse James" and "Days of Jesse James" came out in 1939. The first featured Tyrone Power as Jesse, Henry Fonda as Frank James, and John Carradine as Robert Ford. James was presented in a context that appealed to audiences of the 1930s. James is seen as a rural folk hero pressed into a life of crime due to the oppressive economic climate.
Two movies about Jesse James were produced in the 1940s; "Jesse James at Bay" (1947) starring Roy Rogers and "I Shot Jesse James" (1949) with Reed Hadley. The 1950s produced four movies; "Kansas Raiders" (1950) starring Audie Murphy, "The Great Mississippi Raid" (1951), "Jesse James Women" (1957), "True Story of Jesse James" (1957), and the comedy "Alias Jesse James" (1959) with Bob Hope. According to Terrence Rafferty, film critic for the "New York Times," "True Story" with Robert Wagner offered the most truthful and accurate portrayal of James. The film covers the last 18 years of James' life.
A few James movies were made in the 1960s, including "Jesse James Meets Frankenstein" (1966) and another Murphy-led film, "A Time For Dying" (1969). "The Great Northfield Minnesota Raid" (1972) with Robert Duvall told the story of the ill-fated raid that cost James several of his top men. The movie is dark and gritty and presents James and his gang in a realistic, cruel and unfavorable light. The 1980s movies includes "The Long Riders" (1980), "The Last Days of Frank and Jesse James"(1986). The latter features Kris Kristofferson, Johnny Cash and Willie Nelson.
Several movies about James have between 1990 and 2012. They include "Frank and Jesse" (1994), "Purgatory" (1999), "American Outlaw" (2001), "Jesse James: Legend, Outlaw, Terrorist" (2005) and "The Assassination of Jesse James by the Coward Robert Ford" (2007). The last starred Brad Pitt as James and Casey Affleck as Ford. The nearly 2 1/2 hour film covered the last few months of James' life, which ended in his Missouri cabin when Ford shot him in the back. As of 2011 it was the last major film about James, though a smaller effort, "American Bandits: Frank and Jesse James" with Peter Fonda and George Stults, came out in 2010.