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

->''"He'd a French cocked-hat on his forehead, a bunch of lace at his chin,\\
A coat of the claret velvet, and breeches of brown doe-skin;\\
They fitted with never a wrinkle: his boots were up to the thigh!\\
And he rode with a jewelled twinkle,\\
His pistol butts a-twinkle,\\
His rapier hilt a-twinkle, under the jewelled sky."''
-->--''[[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 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.

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}}.

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.

Not to be confused with the country {{Supergroup}} of [[Music/WaylonJennings Waylon]] and [[Music/WillieNelson Willie]] and [[Music/JohnnyCash Cash]] and [[Music/KrisKristofferson Kris]], though they do sing about being one (for the first verse of the song anyway)...

[[folder:Comic Books]]
* 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!]]"

* 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.”

* 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 ''WesternAnimation/Shrek2'', Shrek, Donkey and Puss in Boots resort to highway robbery to [[spoiler:procure clothes for Shrek, who has turned into a human and is now too small (and too sexy) for his ogre clothes.]]
* ''Film/CarryOnDick'', featuring Creator/SidJames as "Big Dick" Turpin.
* In ''Film/BarryLyndon'', Barry is robbed at a roadside by Captain Feeney and his son. [[AffablyEvil The whole exchange is very polite]].
* Ken Follet's ''Film/ThePillarsOfTheEarth'' and ''Film/WorldWithoutEnd'' both feature scenes with highwaymen.
* The Burns Gang in ''Film/TheProposition''. A band of highwaymen crouching up in the hills of the colonial Australian wilderness. The film does not romanticize their crimes at all.
* In many other Australian Westerns, bushrangers like Film/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.

* 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).
* In the ballad "Sovay", the title character dresses as a highwayman and robs her lover to [[FidelityTest test if he'll give up the ring she gave him]]. He passes--good thing too, since she intended to kill him if he failed.

* Numerous romance novels. To take just one of many examples, Barbara Cartland's ''The Lady and the Highwayman'' seems to be comparatively well known (they made a movie of it, at least).
* The ''Literature/{{Discworld}}'' series has a lot of highwayman scenarios played for laughs. The most common is [[MuggingTheMonster for the travelers to turn the tables]] and rob or otherwise get the better of the highwayman.
** In particular the one in ''Discworld/LordsAndLadies'' who holds up the wizards' coach and gets turned into a pumpkin, and the one in ''Discworld/CarpeJugulum'' who holds up the vampires' coach and gets drained. I think at least one of them also uses the "Your money ''and'' your life!" variant.
** Casanunda, dashing swordsman, gentleman of fortune, and dwarf, has occasionally been a highwayman, although he finds it hard to get taken seriously. People say "I say, it's a lowwayman! A bit short, are we?" and he has to shoot them in the knee. He generally tells his targets to "Kneel and deliver".
** Both books also have Casanunda demonstrating how ''sensible'' highwaymen get through such situations--by making friends with the wizards in the first one and staying the hell away in the second.
** Likewise, in ''Discworld/TheAmazingMauriceAndHisEducatedRodents'' a highwayman unsuccessfully tries to rob the travelling party. They stop the highwayman easily, the hard part is deciding what to do with his belongings.
** It's also mentioned that any highwayman holding up dwarves with the line "Your money or your life!" had best bring a book and packed lunch [[TheMiser while the debate rages on.]]
* ''Literature/TheNameOfTheWind'' has a scene were some [[GentlemanThief very well mannered]] highwaymen accost the chronicler. A major subplot in ''Literature/TheWiseMansFear'' has Kvothe fighting a band of thieves who could charitably be called highwaymen, but are really more like bandits.
* 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]].
* Creator/PatriciaCWrede's ''Literature/MairelonTheMagician'' had a self-styled druid of dubious competence attempting to rob a coach filled with ''professional'' criminals in an effort to get his hands on an enchanted platter he wanted to use for a ritual (which the people in the coach didn't even have). He fails miserably.
* ''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 ''TheThreeRobbers'' by Tomi Ungerer. 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.
* In Creator/StephanieBurgis's ''[[Literature/KatIncorrigible A Most Improper Magick]]'', there is a highwayman haunting the roads. They go to a ball with armed guards.
* 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 the second arc of the ''Raine Benares'' novels by Creator/LisaShearin, Raine is worried about meeting her in-laws to be, as she's the WhiteSheep of a family of pirates, and her fiance the Paladin was raised by low-end nobility. Then at the end of the book she learns that her ''mother-in-law'' is a retired highwaywoman, who met her eventual husband during a hold-up.
* 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.

[[folder:Live Action TV]]
* Highwaymen appear twice in ''Series/{{Blackadder}}''.
** In the first series, Blackadder assembles the seven most evil men in the kingdom, one of whom is a highwayman. He uses the "your money or your life" line, but once he has the money, corrects the "or" to "and".
** In the third series, Blackadder himself becomes a highwayman due to financial difficulties. One of the people he robs has a daughter who'd happily entertain the idea of being seduced by a dashing highwayman, but Blackadder isn't interested. Also featured is The Shadow, who gets the JustLikeRobinHood treatment from the population at large. The Shadow turns out to be a) a highway''[[SamusIsAGirl woman]]''; and b) the [[spoiler: same person who the prince regent is preparing to marry.]]
* ''Series/DoctorWho''
** 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'.
* ''Series/HelpImATeenageOutlaw'' is a British show about three well-intentioned (but not necessarily competent) outlaws during the English Civil War.
* The dashing highwayman, and specifically the romanticisation of Dick Turpin, is [[{{Deconstruction}} deconstructed]] in ''Series/HorribleHistories'' with an Adam Ant parody:
-->Everyone thinks they know the story,\\
Of Dick Turpin's highway glory,\\
But my past is far more gory,\\
I was no saint.\\
You think life is one big antic,\\
My profession is romantic,\\
Hate to be pedantic,\\
But it ain't.\\
I became highwayman,\\
It was daylight robbery.\\
I was no Prince Charming,\\
Nothing dandy about me.\\

* Dick Turpin (see Real Life) had a TV series in the 1970s starring the guy from ''Series/ManAboutTheHouse''.
* ''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.
* In the ''Series/StarTrekTheNextGeneration'' episode "Family", Jean-Luc Picard accuses his nephew Rene, who hasn't seen him since Rene was an infant, of being a highwayman when he greets Picard on the way to their family vineyard in La Barre, France.

* 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.
* "Stand & Deliver" by Music/AdamAndTheAnts is made of this trope.
* 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 "Whiskey in the Jar" is about a highwayman who is betrayed by his woman.
* Another Irish folk song, "Brennan on the Moor" is a classic of the genre popularized by Burl Ives and the Clancy Brothers.
* The Australian song "The Wild Colonial Boy," also known as "Bold Jack Donahue," and its many, many variants.
* The 18th century English broadside ballad "Tyne of Harrow" is a classic example.

[[folder:Newspaper Comics]]
* ''ComicStrip/TheFarSide'' parodies the Wild West stagecoach version in "Semi-desperadoes":
-->"Throw down that strong box or I'll blow your head off!... Well, I'll wing you for sure!... Okay, maybe I'll just climb up there and give you a good Dutch rub."

* Obviously, the subject of Alfred Noyes' "Literature/TheHighwayman".

[[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 [[CrowningMomentOfAwesome 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:Tabletop Games]]
* ''TabletopGame/{{GURPS}} Swashbucklers'' discusses the trope and the related history in some detail, and details a Code of Honor disadvantage for highwayman characters.
* 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.
* Highwaymen are a character occupation choice in ''TabletopGame/{{Warhammer}}'' tabletop RPG, complete with horse and classiness. Ironically, one of the base occupations best suited to enter the class is the road warden, a horseback riding, gun-toting patrolman.

* 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").

[[folder:Video Games]]
* ''Franchise/TheElderScrolls'':
** ''[[VideoGame/TheElderScrollsIIIMorrowind Morrowind]]'':
*** Not far from the FirstTown, you may run into the highwayman Nels Llendo. He will demand 50 gold from a male PlayerCharacter, and will attack if it is not paid. (He's a rather tough enemy for a brand new character.) However, he will instead request a kiss from a female player character. If paid or kissed, you can find him later in the Halfway Tavern in Pelagiad, offering training in "bandit"-like skills (Short Blade, Sneak, and Security).
*** The miscellaneous sidequest "The Beauty and the Bandit" can be started by speaking to the victim of a highway robbery, Maurrie Aurmine. Instead of being upset, she is actually in love with the "handsome" bandit who robbed her. She'll ask you to take her glove to the bandit as a sign of her love. He seems touched by the move and gives you a note to deliver back to Maurrie. If you return to Maurrie she will be overjoyed and will set you up with another NPC depending on your character's sex.
** Randomly-generated [[PettingZooPeople Khajiit]] highwaymen show up in ''[[VideoGame/TheElderScrollsIVOblivion Oblivion]]'', though they're not very gentlemanly; completing certain quests, triggering a one-use GoodBadBug or actually being poor (defined as carrying less than 100 gold and wearing clothing worth less than 10 gold combined) means there's only a ''chance'' that they won't attack you. They're also a bit infamous in the fandom for always demanding 100 gold from you, even if (due to LevelScaling) they're wearing expensive [[RainbowPimpGear Glass armor]] that they could sell for way more.
* 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 his 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.''

* ''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.]]

[[folder:Western Animation]]
* The VillainProtagonist of WesternAnimation/HighwayRat is a bandit who robs travellers of their food.
* 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.
* One of the patrons in a tavern in ''WesternAnimation/OverTheGardenWall'' is a Highwayman who [[BlatantBurglar openly dresses]] and describes himself as a bandit. Far from being classy, he's rather thuggish and [[OneSceneWonder memorably]] bizarre.
--> ''I'm the Highwayman!\\
I make ends meet just like any man\\
I work with my hands\\
If you cross my path,\\
I'll knock you out\\
Drag you off the road\\
Steal your shoes from off your feet\\
I'm the Highwayman\\
Gonna make ends meet…''
* ''WesternAnimation/TheVentureBros'' had [[spoiler:Phantom Limb]] rocking this look during his short stint as "Revenge".
* 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!"