The highwayman rides through British folklore as a dashing rogue in a tricorn hat, but this film pulls that image apart to show the desperation and violence underneath. It traces how robbery on horseback became a fixture of English roads from the seventeenth century onward, as returning soldiers, dispossessed gentry, and opportunists turned to armed theft on routes like the Great North Road, where isolated coaches made easy targets. Historians walk through how newspapers and pamphlets turned figures such as Claude Duval into celebrities, spinning tales of courtesy and charm around men who were, in practice, robbing travelers at gunpoint. The film sets that romantic myth against the reality of the gallows at Tyburn, where highwaymen were hanged in public as a warning, and against the state's growing panic over roads it could not police. Reenactments and period engravings fill out the visual record while the narration keeps returning to the same tension: a criminal underclass mythologized into folk heroes almost as soon as they were caught.