History Main / TheHighwayman

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 to 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.

* An [[https://www.youtube.com/watch?v=cEzak36H6co advert]] for "Gaymers Olde English Cider" has a pair of put upon 17thC servants "go self employed" as highwaymen and rob their former obnoxious upperclass master as highwaymen, domino masks and everything.

* A common enemy in ''ComicBook/LuckyLuke'' stories (sometimes on stagecoaches, sometimes on trains), and ripe for parody. One example started practising his speech ("Halt! ... Not loud enough... Halt! ...Not energetic enough..."), not realizing the stagecoach uphill had dislodged a big boulder and was waiting for it to stop before moving on ("[[OhCrap HALT! HALT!]]")

** Other sketches have highlighted the quirks of other highwaymen: such as the Royalist highwayman who refused to rob supporters of King Charles, and a French highwayman who agreed to take less money off a travller if the man's wife agreed to dance with him.

* As a series about a stagecoach line, the most common villains in ''Series/{{Whiplash}}'' were bushrangers: outlaws who hide in the bush and rob travellers on the road. In "The Actress", the eponymous actress thinks bushrangers must be romantic rogues like the dashing highwaymen in her plays. When she encounters one, she discovers the truth is decidedly less romantic.

* The 2012 version of the ''TabletopGame/IronKingdoms'' RPG has the Highwayman as one of its careers, starting with a horse, mask and enough cash to get a decent gun and supply of ammo as well as abilities focussed on ambush tactics and firing from horseback. As the game requires a character to pick two careers at character creation, this can allow for some interesting combinations.

* The VillainProtagonist of ''WesternAnimation/TheHighwayRat'' is a bandit who robs travellers of their food.

* UsefulNotes/NedKelly and his gang.
* The gentlemanly highwaymen emerged in the late 17th century as the result of the English civil war, which left many royalist noblemen destitute, leaving them only their horses and weapons to make their living. Many viewed themselves as [[KarmicThief Karmic Thieves]], and only robbed from their parliamentarist enemies. One of them, Zachary Howard, even managed to rob and humiliate UsefulNotes/OliverCromwell himself.

* In ''VideoGame/DragonAgeOrigins'', as the player and their group run through Lothering, away from the Darkspawn overrun Ostagar, they encounter a group camped out on the road into town, that politely inform the player that there is a toll necessary to be paid to use the road. Alistair sees right through it and just says "Highwaymen." The player can either pay them, fight them, use their status as a [[MemeticBadass Grey Warden]] to get them to stand down, or use their status as a Grey Warden to ''rob them back.''

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 RichIdiotWithNoDayJob 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}}.

* ''Series/DickTurpin'' (see Real Life) had a TV series in the 1970s starring Richar O'Sullivan )from ''Series/ManAboutTheHouse'').

* Claude Duval certainly earned the gentlemanly part of the trope. Known for being exceedingly polite to his victims (always tipping his hat to the ladies and once returning a silver bottle to a baby who was crying) he was visited by many ladies upon his capture. He also had the words [[TheCharmer "Here lies Du Vail, reader, if male thou art, Look to thy purse; if female, to thy heart Much havoc hath he made of both; for all Men he made stand, and women he made fall." inscribed on his tombstone.]]Supposedly he said to one lady he robbed of her earrings "A wench as damned handsome as ye has no need of such baubles." The woman later refused to bear witness in court as it was "a finer compliment than any my husband has given me in years."

* The gentlemanly highwaymen emerged in the late 17th century as the result of the English civil war, which left many royalist noblemen destitute, leaving them only their horses and weapons to make their living. Many viewed themselves as [[KarmicThief Karmic Thieves]], and only robbed from their parliamentarist enemies. One of them, Zachary Howard, even managed to rob and humiliate UsefulNotes/OliverCromwell, himself.

* The eponymous robbers in the children's book ''Literature/TheThreeRobbers'' by Creator/TomiUngerer. The story was made into a six minute animated short in 1972, and into a full length animated movie in 2007.

Nothing dandy about me.\\

* ''Series/MontyPythonsFlyingCircus'' has the highwayman Dennis Moore, who isn't very good at it. Most of his efforts involve breaking into fancy parties and stealing lupins; after he works out what he is doing wrong he redistributes wealth in such a way as to turn the poor downtrodden people into the new rich overlords, after which he tries to equally divide up the belongings of the people he robs.

* Macheath and his cronies in ''Theatre/TheBeggarsOpera'' (the inspiration for the DarkerAndEdgier ''Theatre/TheThreepennyOpera'') are all highwayman, with Macheath being loosely based on Jack Sheppard and his father-in-law Peachum on Jonathan Wild. Macheath's name is a MeaningfulName ("son of the heath" i.e. "son of the open road").

[[caption-width-right:250:Taking your money and your heart at gunpoint.]]

* Claude Duval certainly earned the gentlemanly part of the trope. Known for being exceedingly polite to his victims (always tipping his hat to the ladies and once returning a silver bottle to a baby who was crying) he was visited by many ladies upon his capture. He also had the words [[TheCharmer "Here lies Du Vail, reader, if male thou art, Look to thy purse; if female, to thy heart Much havoc hath he made of both; for all Men he made stand, and women he made fall." inscribed on his tombstone.]]

* A common enemy in ''ComicBook/LuckyLuke'' stories (sometimes on stagecoaches, sometimes on trains), and ripe for parody. One example started practising his speech ("Halt! ... Not loud enough... Halt! ...Not energetic enough..."), not realizing the stagecoach uphill had dislodged a big boulder and was waiting for it to stop before moving on ("[[OhCrap HALT! HALT!]]"

* ''ComicBoo/{{Asterix}}'':

* ''ComicBook/{{Hawkman}}'' foe the ComicBook/GentlemanGhost was a highwayman before he was hanged (and became a ghost).

* ''Film/PlunkettAndMacleane'' is VeryLooselyBasedOnATrueStory about a pair of highwaymen in 1748.

* In many other Australian Westerns, bushrangers like UsefulNotes/NedKelly, Film/MadDogMorgan, Film/CaptainThunderbolt, and Film/TheOutlawMichaelHowe are portrayed as RobinHood type heroes or antiheroes defying the EvilBrit HangingJudge, Crooked Banker and DirtyCop on behalf of the Irish {{Determined Homesteader}}s.

* Creator/KenFollet's ''Literature/ThePillarsOfTheEarth'' and ''Literature/WorldWithoutEnd'' both feature scenes with highwaymen.

* A bunch of characters in ''Literature/JonathanWild'' by Creator/Henry Fielding'', which is a deliberately heavily fictionalized biography of [[http://en.wikipedia.org/wiki/Jonathan_Wild an actual guy.]]

* Creator/KenFollet's ''Serie/ThePillarsOfTheEarth'' and ''Series/WorldWithoutEnd'' both feature scenes with highwaymen.

* Ken Follet's ''Film/ThePillarsOfTheEarth'' and ''Film/WorldWithoutEnd'' both feature scenes with highwaymen.

* The first verse of the song "Highwayman" by Jimmy Webb, which became the signature song of the country super group The Highwaymen, deals with a highwayman of this type.
* The English folk song "Reynardine" is about a girl who gets seduced by the titular highwayman.
* Music/RunningWild song "White Masque" depicts a folk hero type, who robs lords and marquises.

* Music/LoreenaMcKennitt sung an adaptation of Alfred Noyes poem in her album "The Book of Secrets"
* The '60s folk music group the Highwaymen were also inspired by the poem.
* The Irish folk song (covered by [[Music/ThinLizzy two]] [[Music/{{Metallica}} bands]]) "Whiskey in the Jar" is about a highwayman who is betrayed by his woman.

* The Australian song "The Wild Colonial Boy," also known as "Bold Jack Donahue," and its many, many variants.

[[folder:Real Life]]
* Dick Turpin was a real highwayman who became famous for his mostly-fictional exploits, often being given the Robin Hood treatment. [[TheAllegedCar Alleged cars]] are sometimes named Dick Turpin, because they hold up traffic. (One example: Newt's car in ''Literature/GoodOmens''.) Your choice whether or not you think that's relevant. His modern reputation is a major HistoricalHeroUpgrade, as while lots of highwaymen were known as gentlemanly in their own time, his contemporary reputation was as a cut-throat.
* In a similar vein to Turpin was [[MultipleChoicePast William/John/James]] Nevison, a seventeenth-century highwayman who was probably nearer to an anti-hero but was later [[HistoricalHeroUpgrade upgraded]] to being JustLikeRobinHood. Although Turpin is credited with the famous ride from London to York, it seems more likely that Nevison actually achieved this feat, and it was later ascribed to Turpin by the latter's biographer.
* Black Bart, ([[http://en.wikipedia.org/wiki/Charles_Bolles Charles Bolles,]]) a stagecoach robber of the American Old West.
* [[http://en.wikipedia.org/wiki/Jack_Sheppard Jack Sheppard]], known for being a LovableRogue and his skill at escaping prison, and an inspiration for many fictional versions.
* Claude Duval certainly earned the gentlemanly part of the trope. Known for being exceedingly polite to his victims (always tipping his hat to the ladies and once returning a silver bottle to a baby who was crying) he was visited by many ladies upon his capture. He also had the words [[TheCharmer "Here lies Du Vail, reader, if male thou art, Look to thy purse; if female, to thy heart Much havoc hath he made of both; for all Men he made stand, and women he made fall." inscribed on his tombstone.]]
* UsefulNotes/NedKelly and his gang.
* The gentlemanly highwaymen emerged in the late 17th century as the result of the English civil war, which left many royalist noblemen destitute, leaving them only their horses and weapons to make their living. Many viewed themselves as [[KarmicThief Karmic Thieves]], and only robbed from their parliamentarist enemies. One of them, Zachary Howard, even managed to rob and humiliate UsefulNotes/OliverCromwell, himself.
[[/folder]]

* The indie RPG ''[[https://allisonarth.itch.io/gentleman-bandit Gentleman Bandit]]'' involves being ''such'' a gentlemanly highwayman that you write poetry when not committing crimes.

* 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.
* Highwayman is one of the unit classes in ''VideoGame/BattleForWesnoth''. In contrast to the romantic image of a highwayman, they are the level 3 promotion of the Thug unit and are a rough-looking man on foot armed with a heavy mace.
* In ''VideoGame/DragonAgeOrigins'', as the player and their group run through Lothering, away from the Darkspawn overrun Ostagar, they encounter a group camped out on the road into town, that politely inform the player that there is a toll necessary to be paid to use the road. Alistair sees right through it and just says "Highwaymen." The player can either pay them, fight them, use their status as a [[MemeticBadass Grey Warden]] to get them to stand down, or use their status as a Grey Warden to ''rob them back.''

* The WesternAnimation/{{Classic Disney Short|s}} ''The Robber Kitten'' is about a kitten who dreams of being a highwayman. He runs away from home and finds out the hard way how unglamorous and dangerous it is to be one.
* The Dandy Highwayman in the ''WesternAnimation/ScoobyDooMysteryIncorporated'' episode "Stand and Deliver" never actually stole anything, he just interrupts couples on a date then the woman always decides to go with him.

* WesternAnimation/TheBeatles are held captive by an inept highwayman in "I'll Follow The Sun." They easily escape as the highwayman delivers the ransom note, but by the end of the cartoon, he goes straight and gets a job fixing cars, starting with the boys' car. His shop fees amount to what the boys call altogether "highway robbery!"

* ComicBook/{{Hawkman}} foe the ComicBook/GentlemanGhost was a highwayman before he was hanged (and became a ghost).
* A common enemy in ''ComicBook/LuckyLuke'' stories (sometimes on stagecoaches, sometimes on trains), and ripe for parody. One example started practicing his speech ("Halt! ... Not loud enough... Halt! ...Not energetic enough..."), not realizing the stagecoach uphill had dislodged a big boulder and was waiting for it to stop before moving on ("[[OhCrap HALT! HALT!]]"

* ''Gentleman Jim'' by Raymond Briggs features a well-meaning but simple-minded middle aged man attempting to become a very romanticised highwayman in 20th Century England. On a donkey. On a motorway.

[[folder:Fanfiction]]
* The Yellow Wings in FanFic/TheTaintedGrimoire are an entire group of them. Amusingly, Ensei and Cid were [[MuggingTheMonster far stronger than them]].
* Referenced in ''Fanfic/TheKeysStandAlone: The Soft World'' when John sarcastically suggests that the four become highwaymen in order to sift through the loot of the mine-robbers for the amulet Ringo is hoping to find; "Rob Roy times nine thousand sounds great fun."

[[folder:Film]]
* In the [[TheFilmOfTheBook film]] version of ''Literature/AnneOfGreenGables'', Anne does a dramatic recitation of the poem by Alfred Noyes.
* ''Film/PlunkettAndMacleane'' is VeryLooselyBasedOnATrueStory about a pair of highwaymen in 1748.

* In ''Film/BarryLyndon'', Barry is robbed at a roadside by Captain Feeney and his son. [[AffablyEvil The whole exchange is very polite]].

* Creator/RafaelSabatini wrote many stories about highwaymen, including several concerning the fortunes of a charming rogue who called himself "Captain Evans". (And, well-separated over the course of his career, at least three variations on a plot in which a clever but unpleasant person gets the better of a highwayman, robs ''him'', and then gets caught red-handed with the loot and arrested as the highwayman.)
* ''The Toby Man'' by Creator/DickKingSmith is a children's book about a young boy who becomes a highwayman with the help of talking animals.
* One of Creator/PoulAnderson and Creator/GordonRDickson's ''Literature/{{Hoka}}'' stories mentions that one of the Hokas has taken to dressing up as Dick Turpin and gets hanged every week. (Hanging doesn't actually kill Hokas; it's just one of the many things they adopted from human history and pop culture.)
* Henry Fielding included these in some of his writings. Two examples are a highwayman who tries to rob the title character of ''Literature/TheHistoryOfTomJonesAFoundling'' and is easily overpowered, but uses a sob story to convince Tom to not turn him in. Also, a bunch of characters in ''Jonathan Wild'', which is a deliberately heavily fictionalized biography of [[http://en.wikipedia.org/wiki/Jonathan_Wild an actual guy.]]

* ''Ratcatcher'', the first novel in the Literature/MatthewHawkwood series, opens with a pair of highwaymen robbing a coach and killing a naval messenger. The documents they steal are what drives the plot.
* The eponymous robbers in the children's book ''Literature/TheThreeRobbers'' by Creator/TomiUngerer. The story was made into a six minute animated short in 1972, and into a full length animated movie in 2007.
* Steven Brust's ''Literature/KhaavrenRomances'' series includes a number of highwaymen. One of the main characters also becomes a famous highwayman.

* Bortis in ''Literature/ChroniclesOfTheKencyrath'' is a brigand, and raids caravans going over the mountains. His sometimes-lover Tanis thinks it's sexy. Jame (the main character and narrator) think's it's immoral. His job aside, he's definitely a {{jerkass}}.

* In ''Literature/TheMidnightFolk'', Kay is told a tale about Benjamin the highwayman, who used to live in the area.
* In ''Literature/ACollegeOfMagics'', Faris and her friends are bailed up by bandits in the coach home. They turn out to be the noble and friendly sort, raising money to help the farmers ground down by Faris's wicked uncle, but the point is well made that the other sort are also active in the area.

** In "The Visitation", Richard Mace. He declares he is really an actor forced to this.
** In "The Woman Who Lived", Asildr has adopted an alter-ego as a male highwayman called 'the Knightmare'.

* Dick Turpin (see Real Life) had a TV series in the 1970s starring the guy from ''Series/ManAboutTheHouse''.

* ''Webcomic/ChampionsOfFaraus'' has Dave the highwayman, who, after a failed atempt at robbing the main characters [[spoiler:decides to help them rob a carriage owned by Sarengal's cultists who are transporting an important item.]]

* The eponymous robbers in the children's book ''The Three Robbers'' by Creator/TomiUngerer. The story was made into a six minute animated short in 1972, and into a full length animated movie in 2007.