History Main / TheHighwayman

* 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.

** 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.]]

* 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 ''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 Irish folk song "Whiskey in the Jar" is about a highwayman who is betrayed by his woman.

* 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.

* Prince Sevastian in ''VisualNovel/ReigningPassions'' moonlights as The Silver Dagger, a masked highwayman who robs the wealthy as they travel through the [[EternalWinter 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.

** 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.

** 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.

* 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.''

** 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.

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

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

* 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.

* 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.”

* 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]].

* Black Bart ([[http://en.wikipedia.org/wiki/Charles_Bolles Charles Bolles]]), a stagecoach robber of the American Old West.

->''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.''

* 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}}.

** ''VideoGame/TheElderScrollsIIIMorrowind'' featured a true gentleman robber. So much of a gentleman, in fact, that the associated quest involves pairing him up with his latest victim (she didn't know where he went, so you need to find him and bring him a message, and he didn't think himself worthy of her, so he didn't dare go and find her again).
** Randomly-generated [[PettingZooPeople Khajiit]] highwaymen show up in ''VideoGame/TheElderScrollsIVOblivion'', 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.

* ''Literature/TheNameOfTheWind'' has a scene were some [[GentlemanThief very well mannered]] highwaymen accost the chronicler. A major subplot in ''TheWiseMansFear'' has Kvothe fighting a band of thieves who could charitably be called highwaymen, but are really more like bandits.

* 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.

* In ''WesternAnimation/{{Shrek}} 2'', 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.]]

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

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 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 English Civil War is often blamed for their being ''forced'' to take up the occupation. A common occupation for the hero of a {{Swashbuckler}}.