(There has definitely been at least one YKTTW about highwaymen before, but as far as I can tell, nothing was actually launched, so I'm assuming they became inactive and were discarded. If I'm wrong, this one isn't necessary.) A highwayman, put simply, is a guy who robs people on highways. The archetypal highwayman usually being 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 possibly a mask. At times, highwaymen were seen as glamorous. For various reasons (including the fact that 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?). Highwaymen began to go out of fashion with the development of toll roads (which are older than some people are aware) and steam trains (which get robbed under a different trope). In works written recently, highwaymen tend to appear as parodies or deconstructions more often than they are played straight. Examples:
- 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.
- 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).
- 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).
- Dick Turpin was a real highwayman who became famous for his often-fictional exploits, often being given the Robin Hood treatment.
- Monty Python had the highwayman Dennis Moore.
Hello, Unknown Troper. You'll need to get known to lend a hand here.