Line #18 Main/TheHighwayman


1	[[quoteright:250:https://static.tvtropes.org/pmwiki/pub/images/43_9941.jpg]]
2	[[caption-width-right:250:''[[Music/AdamAnt Stand and deliver\
3	Your money or your life]]'']]
4
5	->''"He'd a French cocked-hat on his forehead, a bunch of lace at his chin,\
6	A coat of the claret velvet, and breeches of brown doe-skin;\
7	They fitted with never a wrinkle: his boots were up to the thigh!\
8	And he rode with a jewelled twinkle,\
9	His pistol butts a-twinkle,\
10	His rapier hilt a-twinkle, under the jewelled sky."''
11	-->-- Alfred Noyes, "Literature/TheHighwayman"
12
13	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 TheWildWest, in which they were known as "road agents". They set up an InescapableAmbush 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.
14
15	At times, highwaymen were seen as a glamorous GentlemanThief 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 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 side occupation for the hero of a {{Swashbuckler}}, when not rescuing the princess from the BigBad Viceroy.
16
17
18	Highwaymanning was not risk-free, as the coachman probably had a flintlock pistol or two, and even the BlueBlood 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 [[DeadlyEuphemism neck stretching]].
19
20	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 by a gang of outlaws 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.
21
22	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)...
23	----
24	!!Examples:
25	[[foldercontrol]]
26
27	[[folder:Advertising]]
28	* 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 upper-class master as highwaymen, domino masks and everything.
29	[[/folder]]
30
31	[[folder:Audio Plays]]
32	* Robin and Oberon are these in ''AudioPlay/ThePrincessThieves''. Robin even announces himself to the Marquis of Chiswick with "stand and deliver!"
33	[[/folder]]
34
35	[[folder:Comic Books]]
36	* ''ComicBook/{{Asterix}}'':
37	** In ''Recap/AsterixAndTheGoldenSickle'', 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.
38	** Asterix and Obelix become victims of two of them while they are sleeping in ''Recap/AsterixAndTheBanquet''.
39	* ''ComicBook/GentlemanJim'' by Creator/RaymondBriggs 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.
40	* The main character from ''ComicBook/GillesDeGeus'' used to be one in the early days of the comic. It was dropped when the comic switched format to full length stories.
41	* ''ComicBook/TheGreenKnight'' fights an antagonistic version of this in ''Dynamic Comics'' #3.
42	* ''ComicBook/{{Hawkman}}'' foe the [[Characters/{{Hawkman}} Gentleman Ghost]] was a highwayman before he was hanged (and became a ghost).
43	* 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!]]")
44	[[/folder]]
45
46	[[folder:Fan Works]]
47	* In ''Fanfic/TheDevilDoesCare'', 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 NervesOfSteel to ''marry fucking {{Dracula}}'', it works out how you think.
48	* 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."
49	* The Yellow Wings in ''FanFic/TheTaintedGrimoire'' are an entire group of them. Amusingly, Ensei and Cid were [[MuggingTheMonster far stronger than them]].
50	[[/folder]]
51
52	[[folder:Films -- Animation]]
53	* 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.]]
54	[[/folder]]
55
56	[[folder:Films -- Live Action]]
57	* In the [[TheFilmOfTheBook film]] version of ''Literature/AnneOfGreenGables'', Anne does a dramatic recitation of the poem by Alfred Noyes.
58	* In ''Film/BarryLyndon'', Barry is robbed at a roadside by Captain Feeney and his son. [[AffablyEvil The whole exchange is very polite]].
59	* ''Film/CarryOnDick'', featuring Creator/SidJames as "Big Dick" Turpin.
60	* In ''Film/CaptainThunderbolt'', Ward behaves like a gentleman when robbing stagecoaches.
61	* ''Film/MadDogMorgan'' is a desperado AntiHero in the mould of UsefulNotes/JesseJames.
62	* ''Film/TheOutlawMichaelHowe'' is about a young bushranger who leads a rebellion against the British during the 1820s
63	* ''Film/PlunkettAndMacleane'' is a VeryLooselyBasedOnATrueStory about a pair of highwaymen in 1748.
64	* 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.
65	[[/folder]]
66
67	[[folder:Folklore]]
68	* Sometimes Myth/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.
69	* 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.
70	[[/folder]]
71
72	[[folder:Literature]]
73	* 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).
74	* 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}}.
75	* 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.
76	* 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.
77	** In particular the one in ''Literature/LordsAndLadies'' who holds up the wizards' coach and gets turned into a pumpkin, and the one in ''Literature/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.
78	** 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".
79	** 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.
80	** Likewise, in ''Literature/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.
81	** 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 [[TheScrooge while the debate rages on.]]
82	** ''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. [[WholesomeCrossdresser If "plain" is the right word]].
83	* ''Literature/DoctorSynTheScarecrow'': 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.
84	* 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.
85	* 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.)
86	* A bunch of characters in ''Literature/JonathanWild'' by Creator/HenryFielding, which is a deliberately heavily fictionalized biography of [[http://en.wikipedia.org/wiki/Jonathan_Wild an actual guy.]]
87	* ''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.
88	* Steven Brust's ''Literature/KhaavrenRomances'' series includes a number of highwaymen. One of the main characters also becomes a famous highwayman.
89	* 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.
90	* In ''Literature/TheMidnightFolk'', Kay is told a tale about Benjamin the highwayman, who used to live in the area.
91	* 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.
92	* Creator/KenFollett's ''Literature/ThePillarsOfTheEarth'' and ''Literature/WorldWithoutEnd'' both feature scenes with highwaymen.
93	* 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.
94	* ''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.
95	* 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.)
96	* 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.
97	* ''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.
98	[[/folder]]
99
100	[[folder:Live Action TV]]
101	* Highwaymen appear twice in ''Series/{{Blackadder}}''.
102	** 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".
103	** 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.]]
104	* ''Series/DoctorWho''
105	** In "[[Recap/DoctorWhoS19E4TheVisitation The Visitation]]", Richard Mace. He declares he is really an actor forced to this because TheBlackDeath has closed all the theatres
106	** In "[[Recap/DoctorWhoS35E6TheWomanWhoLived The Woman Who Lived]]", Asildr has adopted an alter-ego as a male highwayman called 'the Knightmare'.
107	* ''Series/HelpImATeenageOutlaw'' is a British show about three well-intentioned (but not necessarily competent) outlaws during the English Civil War.
108	* The dashing highwayman, and specifically the romanticisation of Dick Turpin, is [[{{Deconstruction}} deconstructed]] in ''Series/HorribleHistories'' with an Adam Ant parody:
109	-->Everyone thinks they know the story,\
110	Of Dick Turpin's highway glory,\
111	But my past is far more gory,\
112	I was no saint.\
113	\
114	You think life is one big antic,\
115	My profession is romantic,\
116	Hate to be pedantic,\
117	But it ain't.\
118	\
119	I became highwayman,\
120	It was daylight robbery.\
121	(Hah!)\
122	I was no Prince Charming,\
123	Nothing dandy about me.
124	** 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.
125	* ''Series/DickTurpin'' (see Real Life) had an eponymous TV series in the 1970s, starring Richard O'Sullivan from ''Series/ManAboutTheHouse''.
126	* Dick Turpin is also the main character in the Creator/AppleTVPlus comedy series ''Series/TheCompletelyMadeUpAdventuresOfDickTurpin'' from 2024, which true to the title is a completely fictional retelling of the story of Dick Turpin, with no historical accuracy whatsoever.
127	* ''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.
128	* In the ''Series/StarTrekTheNextGeneration'' 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.
129	* ''Series/ThievesOfTheWood'' is a 2020 Dutch television series about the adventures of the HistoricalDomainCharacter Jan de Licht and his band of robbers during the early 18th century.
130	* As a series about a stagecoach line, the most common villains in ''Series/{{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.
131	* ''Literature/TheWorstWitch'''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.
132	--> "And although this was long ago, remember if you can/Our founder was no ShrinkingViolet but a highwayman."
133
134	[[/folder]]
135
136	[[folder:Music]]
137	* "Stand & Deliver" by Music/AdamAndTheAnts is made of this trope.
138	* Another Irish folk song, "Brennan on the Moor" is a classic of the genre popularized by Burl Ives and the Clancy Brothers.
139	* The '60s folk music group the Highwaymen were also inspired by the Alfred Noyes poem.
140	* Music/LoreenaMcKennitt sung an adaptation of Alfred Noyes poem in her album "The Book of Secrets".
141	* The English folk song "Reynardine" is about a girl who gets seduced by the titular highwayman.
142	* Music/RunningWild song "White Masque" depicts a folk hero type, who robs lords and marquises.
143	* The 18th century English broadside ballad "Tyne of Harrow" is a classic example.
144	* 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.
145	* 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.
146	* The Australian song "The Wild Colonial Boy," also known as "Bold Jack Donahue," and its many, many variants.
147	[[/folder]]
148
149	[[folder:Newspaper Comics]]
150	* ''ComicStrip/TheFarSide'' parodies the Wild West stagecoach version in "Semi-desperadoes":
151	-->"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."
152	[[/folder]]
153
154	[[folder:Poetry]]
155	* Obviously, the subject of Alfred Noyes' "Literature/TheHighwayman".
156	[[/folder]]
157
158	[[folder:Tabletop Games]]
159	* 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.
160	* In ''TabletopGame/GrimHollow'', the Highway Rider is a Roguish Archetype that involves riding a loyal steed to make hit-and-run attacks.
161	* ''TabletopGame/{{GURPS}} Swashbucklers'' discusses the trope and the related history in some detail, and details a Code of Honor disadvantage for highwayman characters.
162	* 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 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.
163	* 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.
164	[[/folder]]
165
166	[[folder:Theatre]]
167	* Macheath and his cronies in ''Theatre/TheBeggarsOpera'' (the inspiration for the DarkerAndEdgier ''Theatre/TheThreepennyOpera'') 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 MeaningfulName ("son of the heath" i.e. "son of the open road").
168	[[/folder]]
169
170	[[folder:Video Games]]
171	* 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.
172	* 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 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 [[EldritchLocation the Hamlet]] is to [[TheAtoner atone for his crimes.]]
173	* 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 [[TheDreaded Grey Warden]] to get them to stand down, or use their status as a Grey Warden to ''rob them back.''
174	* ''Franchise/TheElderScrolls'':
175	** ''[[VideoGame/TheElderScrollsIIIMorrowind Morrowind]]'':
176	*** 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).
177	*** 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.
178	** Randomly-generated [[CatFolk 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.
179	* ''VideoGame/GameOfThronesAscent'': 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.
180	* In ''VideoGame/MaximoVsArmyOfZin'', ghosts of dead highwaymen are littered throughout the forest and cornfield levels. They are armed with [[GunsAkimbo two equally spectral pistols]], which make you lose your coins if they find their target.
181	-->Your money or your life!
182	* In ''VideoGame/WarOfTheVisionsFinalFantasyBraveExvius'', a royal convoy is attacked, and the 'bandits' try [[FalseFlagOperation to appear to be highwaymen]] to help hide who's ''actually'' behind the attack.
183	[[/folder]]
184
185	[[folder:Visual Novels]]
186	* Prince Sevastian in ''VisualNovel/ReigningPassions'' moonlights as The Silver Dagger, a masked highwayman who robs the wealthy as they travel through the [[EndlessWinter 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.
187	[[/folder]]
188
189	[[folder:Webcomics]]
190	* ''Webcomic/ChampionsOfFaraus'' has Dave the highwayman, who, after a failed attempt at robbing the main characters [[spoiler:decides to help them rob a carriage owned by Sarengal's cultists who are transporting an important item.]]
191	* In ''Webcomic/TheInexplicableAdventuresOfBob'' Fructose Riboflavin's dad was a highwayman [[RecycledInSpace IN SPACE!]]
192	[[/folder]]
193
194	[[folder:Western Animation]]
195	* ''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!"
196	* 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.
197	* ''WesternAnimation/{{Disenchantment}}'': In "[[Recap/DisenchantmentS1E3ThePrincessOfDarkness 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.
198	* The VillainProtagonist of ''WesternAnimation/TheHighwayRat'' is a bandit who robs travelers of their food.
199	* ''WesternAnimation/LooneyTunes'': The Scarlet Pumpernickel's occupation in "WesternAnimation/TheScarletPumpernickel"; a parody of every {{Swashbuckler}} trope ever.
200	* 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.
201	--> ''I'm the Highwayman!\
202	I make ends meet just like any man\
203	I work with my hands\
204	If you cross my path,\
205	I'll knock you out\
206	Drag you off the road\
207	Steal your shoes from off your feet\
208	I'm the Highwayman\
209	Gonna make ends meet…''
210	* 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.
211	* ''WesternAnimation/TheVentureBros'' had [[spoiler:Phantom Limb]] rocking this look during his short stint as "Revenge".
212	[[/folder]]
213
214	[[folder:Real Life]]
215	* 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.
216	* 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.
217	* Black Bart, ([[http://en.wikipedia.org/wiki/Charles_Bolles Charles Bolles,]]) a stagecoach robber of the American Old West.
218	* [[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.
219	* 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."
220	%%* UsefulNotes/NedKelly and his gang.
221	* 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.
222	* 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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Context Main / TheHighwayman