As it happens, old Jack Sheppard (see yesterday’s post) did a little bit of Highwayman-ing himself back in the early 1700s. It was all the rage then. South London looms large in this story, long before it became H’s stomping ground: for many years, well to-do pilgrims heading for Canterbury, and travelers heading for the coast, had to take their chances running the gauntlet that was the Dover Road, especially at places like Gad’s Hill and Shooter’s Hill.
The Highwayman, with his well-worn cries of Stand and Deliver! and Your Money or Your Life!, actually had his origins in the English Civil War, when large numbers of Royalist, Cavalier supporters of King Charles I found themselves without position or income – their estates confiscated, their status reduced. Some of them - figures such as Captain Phillip Stafford and Captain James Hind – resorted to crime and set the tone for succeeding generations of gentlemen robbers whose bark was often worse than their bite.
Best known of all, or course, was Dick Turpin, who worked the Great North Road. But the Highwayman era was not to last much beyond the 17th and 18th centuries. The Bow Street Horse Patrol around London got going in the 1760s, and the founding of the Metropolitan Police in 1829 seems to have put an end to the matter. It seems likely, though, that the Western movie archetype of the stagecoach-robbing, gun-toting outlaw with a scarf tied across the lower part of his face was set by these gentlemen.