Highwaymen
Mounted robbers who frequented the country roads around London and many other places in England from around the 16th to the end of the 18th centuries. They either worked alone or in small groups, stopping coaches at pistol point and demanding money and articles of value. Their catch phrase was "Stand and deliver." Despite the presence of weapons, the use of violence in these acts was uncommon. Instead, the robbers were famous for their gentlemanly behaviour.
Legal status
Although the reclusion of the country roads provided relative safety for the highwaymen, the task wasn't without risk, as the penalty for armed robbery was hanging, and many of the more prominent members of this professional group were actually executed.
Public opinion
While the state persecuted the highwaymen with the full rigor of the law, the public opinion often considered them heroes in the tradition of robbers like Robin Hood. "Stage names" like Sixteen String Jack were widely known, and the subject in question was famous for his extravagant clothing, his lavish lifestyle and his quick-witted, disrespectful attitude in the face of authorities. In these aspects, the highwaymen - who were furthermore mostly younger than 30 and often perceived as charming and good looking - resemble modern pop stars.
The Beggar's Opera
John Gay's opera bears witness to this popularity, as the highwayman Jack Sheppard (born 1702, executed in 1724) became Gay's model for the character of Captain Macheath.
Decline
Highwaymen became an uncommon encounter at the end of the 18th century due to the expansion of the British road system, as the rising number of guarded toll gates provided better protection against criminals.
Sources
Smith, Captain Alexander: Von der Wiege bis zum Galgen. Leben und Taten der berühmtesten Straßenräuber, Mörder und Spitzbuben [Complete history of the lives and robberies of the most notorious highwaymen, footpads, shoplifts and cheats of both sexes]. Trans. anonymous. Tübingen: Erdmann, 1974.
Harper, Charles George: Half-hours with the highwaymen: picturesque biographies and traditions of the „knights of the road“. London: Chapman & Hall, 1908.