To travelers on dark English roads in the 17th and 18th centuries, highwaymen were dangerous criminals. But to the general public, before and after, these mysterious bandits, some of whom styled themselves as fallen gentlemen or Cavaliers, were glamorous figures. Ever since, they've been the subject of song and story.
The Beggar's Opera, featuring a love story surrounding the condemned highwayman Macheath, was a mega-hit when it debuted in 1728 and continues to be performed. (This video is from the 1983 version, featuring Roger Daltrey as Macheath.)
With all due respect to Adam Ant and Roger Daltrey, to me the highwayman will always be the romantic title character of Alfred Noyes' 1906 poem "The Highwayman," here set to music by Loreena Mckennitt.
Glamour, however, always conceals something, and in the case of glamorous outlaws, that something is often neither particularly attractive nor even impressive--as this debunking of Dick Turpin, one of Britain's most famous highwaymen, demonstrates.