The Highwayman

Stand and deliver
Your money or your life

"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."

— Alfred Noyes, "The Highwayman"

A highwayman, put simply, is a guy who robs people traveling in carriages on old-fashioned roads. The archetypal highwayman who is usually invoked by the word was found in Britain between, say, the years 1500 and 1800, although the same tactics went on elsewhere and elsewhen, particularly The Wild West, in which they were known as "road agents". They set up an Inescapable Ambush 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 sword-and-gun combo, and perhaps a Domino Mask 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 a glamorous Gentleman Thief type. 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 Gentleman Thief of armed robbery. Some of them were built up as folk heroes ("...Just Like Robin Hood!"), and they have also been stock Love Interests in romance novels (perhaps because All Girls Want Bad Boys?). In certain types of story, it's also quite likely that 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 woman to avoid being known as such. Popular in The Cavalier Years, where the English Civil War is often blamed for their being forced to take up the occupation. A common side occupation for the hero of a Swashbuckler, when not rescuing the princess from the Big Bad Viceroy.

Highwaymanning was not risk-free, as the coachman probably had a flintlock pistol or two, and even the Blue Blood passenger might have a Derringer or small musket. As well, the authorities would hunt for notorious highwaymen so that they could give them a good neck stretching.

Highwaymanning became less attractive as a career with the development of toll roads (which are older than some people realise), steam trains (which get robbed by a gang of outlaws under a different trope), and organised police forces. In works written recently, highwaymen tend to appear as parodies or deconstructions more often than they are played straight. Even so, elements of this trope persisted in the archetype of the pulp-era Proto-Superhero, many of which could be considered the urban successors of Just Like Robin Hood highwaymen.

Not to be confused with the country Supergroup of Waylon and Willie and Cash and Kris, though they do sing about being one (for the first verse of the song anyway)...

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Examples:

Advertising

• An advert for "Gaymers Olde English Cider" has a pair of put upon 17thC servants "go self employed" as highwaymen and rob their former obnoxious upper-class master as highwaymen, domino masks and everything.

Audio Plays

• Robin and Oberon are these in The Princess Thieves. Robin even announces himself to the Marquis of Chiswick with "stand and deliver!"

Comic Books

• Asterix:
  • In Asterix and the Golden Sickle, the forests between the village and Lutetia are infamous for being infested with these. Asterix and Obelix run into several of them along the way.
  • Asterix and Obelix become victims of two of them while they are sleeping in Asterix and the Banquet.
• 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.
• The main character from Gilles de Geus used to be one in the early days of the comic. It was dropped when the comic switched format to full length stories.
• The Green Knight fights an antagonistic version of this in Dynamic Comics #3.
• Hawkman foe the Gentleman Ghost was a highwayman before he was hanged (and became a ghost).
• A common enemy in Lucky Luke 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 ("HALT! HALT!")

Fan Works

• In The Devil Does Care!, Lisa encounters Trevor when she tries to mug her with a knife on her way to the castle. Since Trevor is a heavily wounded preteen child with nothing but a small knife and Lisa had Nerves of Steel to marry fucking Dracula, it works out how you think.
• Referenced in The Keys Stand Alone: 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."
• The Yellow Wings in The Tainted Grimoire are an entire group of them. Amusingly, Ensei and Cid were far stronger than them.

Films — Animation

• In Shrek 2, Shrek, Donkey and Puss in Boots resort to highway robbery to procure clothes for Shrek, who has turned into a human and is now too small (and too sexy) for his ogre clothes.

Films — Live Action

• In the film version of Anne of Green Gables, Anne does a dramatic recitation of the poem by Alfred Noyes.
• In Barry Lyndon, Barry is robbed at a roadside by Captain Feeney and his son. The whole exchange is very polite.
• Carry On Dick, featuring Sid James as "Big Dick" Turpin.
• In Captain Thunderbolt, Ward behaves like a gentleman when robbing stagecoaches.
• Mad Dog Morgan is a desperado Anti-Hero in the mould of Jesse James.
• The Outlaw Michael Howe is about a young bushranger who leads a rebellion against the British during the 1820s
• Plunkett & Macleane is a Very Loosely Based on a True Story about a pair of highwaymen in 1748.
• The Burns Gang in The Proposition. A band of highwaymen crouching up in the hills of the colonial Australian wilderness. The film does not romanticize their crimes at all.

Folklore

• Sometimes Robin Hood 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.
• In the ballad "Sovay", the title character dresses as a highwayman and robs her lover to 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.

Literature

• 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).
• Bortis in Chronicles of the Kencyrath 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 A College of Magics, 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.
• The Discworld series has a lot of highwayman scenarios played for laughs. The most common is for the travelers to turn the tables and rob or otherwise get the better of the highwayman.
  • In particular the one in Lords and Ladies who holds up the wizards' coach and gets turned into a pumpkin, and the one in Carpe Jugulum 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 The Amazing Maurice and His Educated Rodents 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 while the debate rages on.
  • The Thieves Guild Diary lists highwayman as one of the guild professions. As noted in the trope description, if you don't have a horse (and, for preference, a tricorn hat and a lace collar), you're just a footpad; also a respectable career, but a less romantic one. It's also mentioned that one highwayman who only asked for a kiss from lady passengers was recently arrested by Corporal Nobbs in plain clothes. If "plain" is the right word.
• Doctor Syn ("The Scarecrow"): Syn is friendly with local highwayman Jimmie Bone — who is actually as good a horseman as Syn, and who sometimes impersonates the Scarecrow for purposes of trickery and helping keep Syn's secret.
• A highwayman who tries to rob the title character of The History of Tom Jones, A Foundling and is easily overpowered, but uses a sob story to convince Tom to not turn him in.
• One of Poul Anderson and Gordon R. Dickson's 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.)
• A bunch of characters in Jonathan Wild by Henry Fielding, which is a deliberately heavily fictionalized biography of an actual guy.
• The Name of the Wind has a scene were some very well mannered highwaymen accost the chronicler. A major subplot in The Wise Man's Fear has Kvothe fighting a band of thieves who could charitably be called highwaymen, but are really more like bandits.
• Steven Brust's Khaavren Romances series includes a number of highwaymen. One of the main characters also becomes a famous highwayman.
• Patricia C. Wrede's Mairelon the Magician 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.
• In The Midnight Folk, Kay is told a tale about Benjamin the highwayman, who used to live in the area.
• In Stephanie Burgis's A Most Improper Magick, there is a highwayman haunting the roads. They go to a ball with armed guards.
• Ken Follett's The Pillars of the Earth and World Without End both feature scenes with highwaymen.
• In the second arc of the Raine Benares novels by Lisa Shearin, Raine is worried about meeting her in-laws to be, as she's the White Sheep 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.
• Ratcatcher, the first novel in the Matthew Hawkwood series, opens with a pair of highwaymen robbing a coach and killing a naval messenger. The documents they steal are what drives the plot.
• Rafael Sabatini 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 eponymous robbers in the children's book The Three Robbers by Tomi Ungerer. The story was made into a six-minute animated short in 1972, and into a full length animated movie in 2007.
• The Toby Man by Dick King-Smith is a children's book about a young boy who becomes a highwayman with the help of talking animals.

Live Action TV

• Highwaymen appear twice in 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 Just Like Robin Hood treatment from the population at large. The Shadow turns out to be a) a highwaywoman; and b) the same person who the prince regent is preparing to marry.
• Doctor Who
  • In "The Visitation", Richard Mace. He declares he is really an actor forced to this because The Black Death has closed all the theatres
  • In "The Woman Who Lived", Asildr has adopted an alter-ego as a male highwayman called 'the Knightmare'.
• Help! I'm a Teenage Outlaw 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 deconstructed in Horrible Histories 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.
  (Hah!)
  I was no Prince Charming,
  Nothing dandy about me.
  • 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 traveler if the man's wife agreed to dance with him.
• Dick Turpin (see Real Life) had an eponymous TV series in the 1970s, starring Richard O'Sullivan from Man About the House.
• Dick Turpin is also the main character in the Apple TV+ comedy series The Completely Made-Up Adventures of Dick Turpin from 2024, which true to the title is a completely fictional retelling of the story of Dick Turpin, with no historical accuracy whatsoever.
• Monty Python's Flying Circus 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 Star Trek: The Next Generation episode "Family", Jean-Luc Picard jokingly 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.
• Thieves of the Wood is a 2020 Dutch television series about the adventures of the Historical Domain Character Jan de Licht and his band of robbers during the early 18th century.
• As a series about a stagecoach line, the most common villains in Whiplash were bushrangers: outlaws who hide in the bush and rob travelers 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 Worst Witch's 90s TV adaptation reveals that the founder of Cackle's Academy had a secret identity as a highwayman who robbed from the rich and gave to the poor. The girls are inspired to put on a performance honoring her deeds.
  "And although this was long ago, remember if you can/Our founder was no Shrinking Violet but a highwayman."

Music

• "Stand & Deliver" by Adam and the Ants is made of this trope.
• Another Irish folk song, "Brennan on the Moor" is a classic of the genre popularized by Burl Ives and the Clancy Brothers.
• The '60s folk music group the Highwaymen were also inspired by the Alfred Noyes poem.
• Loreena McKennitt sung an adaptation of Alfred Noyes poem in her album "The Book of Secrets".
• The English folk song "Reynardine" is about a girl who gets seduced by the titular highwayman.
• Running Wild song "White Masque" depicts a folk hero type, who robs lords and marquises.
• The 18th century English broadside ballad "Tyne of Harrow" is a classic example.
• 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 Irish folk song (covered by two 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.

Newspaper Comics

• The Far Side 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."

Poetry

• Obviously, the subject of Alfred Noyes' "The Highwayman".

Tabletop Games

• The indie RPG Gentleman Bandit involves being such a gentlemanly highwayman that you write poetry when not committing crimes.
• In Grim Hollow, the Highway Rider is a Roguish Archetype that involves riding a loyal steed to make hit-and-run attacks.
• 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 Iron Kingdoms 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 focused 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 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.

Theatre

• Macheath and his cronies in The Beggar's Opera (the inspiration for the Darker and Edgier The Threepenny Opera) are all highwaymen, with Macheath being loosely based on Jack Sheppard and his father-in-law Peachum on Jonathan Wild. Macheath's name is a Meaningful Name ("son of the heath" i.e. "son of the open road").

Video Games

• Highwayman is one of the unit classes in Battle for Wesnoth. 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.
• One of the classes in Darkest Dungeon is this. The Highwayman uses 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 and the the Shieldbreaker. His backstory comic also averts the usual romanticizing of the trope by showing him as a ruthless killer, and the reason he has traveled to the Hamlet is to atone for his crimes.
• In Dragon Age: Origins, 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 Grey Warden to get them to stand down, or use their status as a Grey Warden to rob them back.
• The Elder Scrolls:
  • Morrowind:
    • Not far from the First Town, you may run into the highwayman Nels Llendo. He will demand 50 gold from a male Player Character, 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 Khajiit highwaymen show up in Oblivion, though they're not very gentlemanly; completing certain quests, triggering a one-use Good Bad Bug 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 Level Scaling) they're wearing expensive Glass armor that they could sell for way more.
• Game of Thrones: Ascent: Ser Launcil Hallar, Septa Eleanor's former fiance, now a member of the Brotherhood Without Banners, who kidnaps Eleanor to convince her to elope with him.
• In Maximo vs. Army of Zin, ghosts of dead highwaymen are littered throughout the forest and cornfield levels. They are armed with two equally spectral pistols, which make you lose your coins if they find their target.
  Your money or your life!
• In War of the Visions: Final Fantasy Brave Exvius, a royal convoy is attacked, and the 'bandits' try to appear to be highwaymen to help hide who's actually behind the attack.

Visual Novels

• Prince Sevastian in Reigning Passions moonlights as The Silver Dagger, a masked highwayman who robs the wealthy as they travel through the Winter Wilds on the way in or out of the kingdom's capital city and distributes his stolen loot to the poor and needy. He's also one of the title's initial two love interests, in keeping with the romantic associations of the highwayman archetype.

Webcomics

• Champions of Far'aus has Dave the highwayman, who, after a failed attempt at robbing the main characters decides to help them rob a carriage owned by Sarengal's cultists who are transporting an important item.
• In The Inexplicable Adventures of Bob! Fructose Riboflavin's dad was a highwayman IN SPACE!

Western Animation

• The Beatles 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!"
• The Classic Disney Short 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.
• Disenchantment: In "The Princess of Darkness", the trio of criminals Bean helped with ransacking the royal tomb later show up again, having turned to this kind of crime. However, they insist on calling themselves highway-people since their leader is a woman and they want to remain gender-neutral.
• The Villain Protagonist of The Highway Rat is a bandit who robs travelers of their food.
• Looney Tunes: The Scarlet Pumpernickel's occupation in "The Scarlet Pumpernickel"; a parody of every Swashbuckler trope ever.
• One of the patrons in a tavern in Over the Garden Wall is a Highwayman who openly dresses and describes himself as a bandit. Far from being classy, he's rather thuggish and 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…
• The Dandy Highwayman in the Scooby-Doo! Mystery Incorporated episode "Stand and Deliver" never actually stole anything, he just interrupts couples on a date then the woman always decides to go with him.
• The Venture Bros. had Phantom Limb rocking this look during his short stint as "Revenge".

Real Life

• Dick Turpin was a real highwayman who became famous for his mostly-fictional exploits, often being given the Robin Hood treatment. Alleged cars are sometimes named Dick Turpin, because they hold up traffic. (One example: Newt's car in Good Omens.) Your choice whether or not you think that's relevant. His modern reputation is a major Historical Hero Upgrade, 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 William/John/James Nevison, a seventeenth-century highwayman who was probably nearer to an anti-hero but was later upgraded to being Just Like Robin Hood. 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, (Charles Bolles,) a stagecoach robber of the American Old West.
• Jack Sheppard, known for being a Lovable Rogue 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 "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 Karmic Thieves, and only robbed from their Parliamentarist enemies. One of them, Zachary Howard, even managed to rob and humiliate Oliver Cromwell himself.
• 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 infeasible, as simultaneously keeping coachman, passengers, and footmen/guards under control demanded multiple armed men).

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