Jesse James was the most famous member of the James-Younger Gang, media heroes of the 19th Century who committed numerous daring and celebrated robberies in the period following the Civil War. The James-Younger Gang had its roots in a group of demobilized Confederate veterans who had served under guerilla leader Archie Clement, and who continued anti-government actions under Clement after the official end of the war. Its core and classic lineup included brothers Jesse and Frank James, and Cole Younger and several of his siblings.

The gang was responsible for a series of spectacular bank robberies throughout the West and Midwest, beginning in roughly 1868; and soon became folk heroes, expanded their repertoire to include stagecoach and train robberies. A high point was the robbery of a Kansas City fair in full view of a supportive crowd. A botched bank robbery in 1876 split the gang by family, and Frank soon left as well, leaving Jesse to work alone. An attempt in 1882 to form a new gang in Missouri yielded traitors, Robert and Charley Ford, who were in league with the state's governor. Robert Ford shot James dead on April 3 of that year, for $10,000 in reward money. James' wife Zee would die alone and in poverty, while the publicly reviled Charley and Robert Ford weathered murder charges, were pardoned, and died respectively of suicide and murder, in 1884 and 1892. James's epitaph, chosen by his mother, reads, "In Loving Memory of my Beloved Son, Murdered by a Traitor and Coward Whose Name is not Worthy to Appear Here."