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He'd a French cocked-hat on his forehead, a bunch of lace at his chin,His rapier hilt a-twinkle, under the jewelled sky.
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,
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. 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 sword-and-gun combo, and perhaps a Domino Mask.
At times, highwaymen were seen as glamorous. For various reasons (including the fact that they often 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 Rich Idiot With No Day Job 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.
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 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.
- Hawkman foe the Gentleman Ghost was a highwayman before he was hanged (and became a ghost).
- In the film version of Anne of Green Gables, Anne does a dramatic recitation of the poem by Alfred Noyes.
- Plunkett and Macleane is Very Loosely Based on a True Story about a pair of highwaymen in 1748.
- On 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.
- Carry On Dick, featuring Sid James as "Big Dick" Turpin.
- In Barry Lyndon, Barry is robbed at a roadside by Captain Feeney and his son. The whole exchange is very polite.
- Ken Follet's The Pillars of the Earth and World Without End both feature scenes with highwaymen.
- 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).
- 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.
- 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 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.
- 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 Toby Man by Dick King-Smith is a childrens book about a young boy who becomes a highwayman with the help of talking animals.
- One of Poul Anderson'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.)
- Henry Fielding included these in some of his writings. Two examples are a highwayman who tries to rob the title character of Tom Jones and is easily overpowered, but uses asob 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 an actual guy.
- The novel 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.
- Ratcatcher, the first novel in the Matthew Hawkwood series, opens with a pair of highwayen 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 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.
- Steven Brust's The Phoenix Guards series includes a number of highwaymen. One of the main characters also becomes a famous highwayman.
- 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.
- Monty Python's Flying Circus has the highwayman Dennis Moore. It goes without saying that he isn't very good at it. Most of his efforts involve breaking into fancy parties and stealing flowers; 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.
- Help! I'm a Teenage Outlaw is a British show about three well-intentioned (but not necessarily competent) outlaws during the English Civil War.
- Dick Turpin (see Real Life) had a TV series in the 1970s starring the guy from Man About the House.
- In Doctor Who episode "The Visitation", Richard Mace. He declares he is really an actor forced to this.
- 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'm a vicious highwayman,
It's daylight robbery.
I was no Prince Charming,
Nothing dandy about me.
- 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.
- Running Wild song "White Masque" depicts a folk hero type, who robs lords and marquises.
- "Stand & Deliver" by Adam Ant is made of this trope.
- Loreena McKennitt sung an adaptation of Alfred Noyes poem in her album "The Book of Secrets"
- Irish folk song "Whiskey in the Jar" is about a highwayman who is betrayed by his woman.
- Alfred Noyes' The Highwayman.
- 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 a Type 4 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.
- All those on this list
- 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.
- Macheath and his cronies in The Beggars Opera (the inspiration for the Darker and Edgier The Threepenny Opera) 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 Meaningful Name ("son of the heath" i.e. "son of the open road").
- Randomly-generated Khajiit highwaymen show up in The Elder Scrolls IV: 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.
- 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.