History Main / TheHighwayman

* Condemned highwayman Francis Jackson wrote a treatise on the business of highway robbery while awaiting execution in Newgate prison. His text was published in 1674, and achieved considerable popularity, despite it debunking several elements of this trope (e.g. pointing out that robbing rich carriages as a ''solo'' bandit was practically unheard-of, as keeping coachman, passengers, and footmen/guards under simultaneous control demanded multiple gunmen).

* Sometimes RobinHood has some of the qualities that make a highwayman, but on the whole, he's generally in a class of his own (and is a bit early for the highwayman fad in any case). Given that a major (for the era) highway connecting London to York passed through Sherwood Forest, literal highway robbery was likely a staple of his thieving career.

* One of the classes in ''VideoGame/DarkestDungeon'' is this. The highwayman uses [[SwordAndGun a dirk and a pistol]], excels at all ranges except the very back (and even then he can still shoot), and his mobility is only shorter than the jester's. His backstory comic also averts the usual romanticizing of the trope by showing him as a ruthless killer.

-->--''[[http://en.wikisource.org/wiki/The_Highwayman_(Noyes) The Highwayman]]''

A highwayman, put simply, is a guy who robs people on highways. The archetypal highwayman who is usually invoked by the word was found in Britain between, say, the years 1500 and 1800, although the same basic stuff went on elsewhere and elsewhen, particularly TheWildWest, in which they were known as road agents. They interrupt the journeys of rich people riding in coaches to say things like "your money or your life!" and "stand and deliver!". Standard gear seems to include a black outfit (possibly including a hat with a feather in it), a [[SwordAndGun sword-and-gun combo]], and perhaps a DominoMask and above all a horse since that allowed them a quick escape. Armed robbers who weren't mounted were known as footpads.

At times, highwaymen were seen as glamorous. For various reasons (including the fact that they rode horses) they were considered a cut above common bandits. A proper highwayman, instead of being scruffy and furtive, was dashing and debonair--truly the GentlemanThief of armed robbery. Some of them were built up as [[FolkHero folk heroes]] ("...JustLikeRobinHood!"), and they have also been stock LoveInterests in romance novels (perhaps because AllGirlsWantBadBoys?). In certain types of story, it's also quite likely that [[SecretIdentity secret identities]] will be involved--voluminous cloaks and nocturnal tendencies make it relatively easy for a prominent citizen to conceal who they are, or for a [[SweetPollyOliver woman to avoid being known as such]]. Popular in TheCavalierYears, where the UsefulNotes/EnglishCivilWar is often blamed for their being ''forced'' to take up the occupation. A common occupation for the hero of a {{Swashbuckler}}.

Highwaymanning became less attractive as a career with the development of toll roads (which are [[OlderThanTheyThink older than some people realise]]), steam trains (which get robbed under [[TrainJob a different trope]]), and [[UsefulNotes/BritishCoppers organised police forces]]. In works written recently, highwaymen tend to appear as [[{{Parody}} parodies]] or [[{{Deconstruction}} deconstructions]] more often than they are played straight. Even so, elements of this trope persisted in the archetype of the pulp-era ProtoSuperhero, many of which could be considered the urban successors of JustLikeRobinHood highwaymen.