"Captain" James Maclaine was an Irish man of a respectable presbyterian family who had a brief but notorious career as a mounted highwayman in London with his accomplice William Plunkett. He was known as "The Gentleman Highwayman" as a result of his courteous behaviour during his robberies, and obtained a certain kind of celebrity. Notoriously, he held up and robbed Horace Walpole at gunpoint: eventually he was hanged at Tyburn.

A highwayman was a robber who stole from travellers. This type of thief usually travelled and robbed by horse as compared to a footpad who travelled and robbed on foot; mounted highwaymen were widely considered to be socially superior to footpads. Such criminals operated until the mid- or late 19th century. Highwaywomen, such as Katherine Ferrers, were said to also exist, often dressing as men, especially in fiction.