AskDefine | Define highwayman

Dictionary Definition

highwayman n : a holdup man who stops a vehicle and steals from it [syn: highjacker, hijacker, road agent]

User Contributed Dictionary



compound highway + man


  • (Canada) /ˈhaɪˌweɪmən/


  1. A person who robbed travellers on public roads.

Related terms


a person who robbed travellers on roads

Extensive Definition

The word highwayman is first attested from the year 1017. Robbers operated in Great Britain and Ireland from the Elizabethan period until the early 19th century. The term 'highwayman' is mainly applied to robbers who travelled on horseback, as opposed to those who robbed on foot (foot-pads). Mounted robbers were widely considered to be socially superior to foot-pads. Slang names for them included 'knights of the road' and 'gentlemen of the road'. In the mid to late 19th century American West, highwaymen were known as road agents.

Robber heroes

There is a long history of treating highway robbers as heroes. Originally they were admired by many because they were considered to be bold men who confronted their victims face-to-face and were ready to fight for what they wanted. The most famous English robber hero is the legendary medieval outlaw Robin Hood. Later robber heroes included the Cavalier highwayman James Hind, the debonair French highwayman Claude Du Vall, Dick Turpin and 'Sixteen-string Jack' (John Rann). Some highwaymen were remembered as Robin Hood-like figures who robbed those who deserved it and helped people in trouble.

Modus operandi

Some highwaymen robbed alone, but others operated in pairs or in small gangs. They often targeted coaches, including public stagecoaches; the post-boys who carried the mail were also frequently held up. The famous demand to 'Stand and deliver!' (sometimes in forms such as 'Stand and deliver your purse!' or 'Stand and deliver your money!') was in use from the 17th century:
A fellow of a good Name, but poor Condition, and worse Quality, was Convicted for laying an Embargo on a man whom he met on the Road, by bidding him Stand and Deliver, but to little purpose; for the Traveller had no more Money than a Capuchin, but told him, all the treasure he had was a pound of Tobacco, which he civilly surrendred. (The Proceedings of the Old Bailey, 25 April 1677)
The phrase 'Your money or your life' is mentioned in trial reports from the middle of the eighteenth century:
Evidence of John Mawson: 'As I was coming home, in company with Mr. Andrews, within two fields of the new road that is by the gate-house of Lord Baltimore, we were met by two men; they attacked us both: the man who attacked me I have never seen since. He clapped a bayonet to my breast, and said, with an oath, Your money, or your life! He had on a soldier's waistcoat and breeches. I put the bayonet aside, and gave him my silver, about three or four shillings.' (The Proceedings of the Old Bailey, 12 September 1781)

Dangerous places

Highwaymen often lay in wait on the main roads radiating from London. They usually chose lonely areas of heathland or woodland. Hounslow Heath was a favourite haunt: it was crossed by the roads to Bath and Exeter. Bagshot Heath in Surrey was another dangerous place on the road to Exeter. One of the most notorious places in England was Shooter's Hill on the Great Dover Road. Finchley Common, on the Great North Road, was very nearly as bad. Many other places could be mentioned.h


The penalty for robbery with violence was hanging, and most notorious highwaymen ended on the gallows. The chief place of execution for London and Middlesex was Tyburn. Famous highwaymen who ended their lives there included Claude Du Vall, James Maclaine and Sixteen-string Jack. Highwaymen who could go to the gallows laughing and joking, or at least showing no fear, are said to have been admired by many of the people who came to watch.


After about 1815 mounted robbers are recorded only rarely. The last recorded robbery by a mounted highwayman occurred during 1831. The development of the railways is sometimes cited as a factor, but highwaymen were already obsolete before the railway network was built. A very important factor was the expansion of the system of turnpikes, manned and gated toll-roads, which made it all but impossible for a highwayman to escape notice while making his getaway. At the same time, London was becoming much better policed: in 1805 a body of mounted police began to patrol the districts around the city at night. London was growing rapidly, and some of the most dangerous open spaces near the city, such as Finchley Common, were being covered with buildings. A greater use of banknotes, more traceable than gold coins, also made life more difficult for robbers.

Irish highwaymen

In 17th, 18th and early 19th century Ireland acts of robbery were often part of a tradition of popular resistance to British colonial rule and settlement and Protestant domination. From the mid-17th century, Irish bandits who harassed the British were known as 'tories' (from Irish tórai, raider). Later in the century they became known as 'rapparees'. Famous Irish highwaymen included James Freney, Willie Brennan and Jeremiah Grant.

Highwaymen in literature and popular culture

In Shakespeare's King Henry IV Part I Sir John Falstaff is a highwayman, and part of the action of the play concerns a robbery committed by him and his companions. Apart from Falstaff, the most famous highwayman in English drama is Captain Macheath, hero of John Gay's 18th-century ballad opera The Beggar's Opera. The modern legend of Dick Turpin owes an enormous amount to Harrison Ainsworth's best-selling novel Rookwood (1834), in which a heavily fictionalised Turpin is one of the main characters. Alfred Noyes's narrative poem 'The Highwayman' has been immensely popular ever since its publication in 1906.
There were many broadsheet ballads about highwaymen; these were often written to be sold on the occasion of a famous robber's execution. A number of highwaymen ballads have remained current in oral tradition in England and Ireland.
From the early 18th century collections of short 'lives' of highwaymen and other notorious criminals became very popular. The earliest of these is Captain Alexander Smith's Complete History of the Lives and Robberies of the Most Notorious Highwaymen (1714). Some later collections of this type had the words 'Newgate Calendar' in their titles and this has become a general name for this kind of publication.
The highwayman known as Juraj Jánošík (1688–1713) became a hero of many folk legends in the Slovak, Czech, and Polish cultures by the 19th century that hundreds of literary works about him have since been published. The first Slovak feature film was Jánošík, made in 1921, followed by seven more Slovak and Polish films about him.
In the later 19th century highwaymen such as Dick Turpin were the heroes of a number of 'penny dreadfuls', stories for boys published in serial form. In the 20th century the handsome highwayman became a stock character in historical love romances, including books by Baroness Orczy and Georgette Heyer.
The Carry On films included a highwayman spoof in Carry On Dick (1974). The Monty Python team sent up the highwayman legends in the Dennis Moore sketch in episode 37 of Monty Python's Flying Circus. In Blackadder the Third, Mr. Edmund Blackadder turns highwayman in the episode Amy and Amiability. In the British children's television series Dick Turpin, starring Richard O'Sullivan, the highwayman was depicted as an 18th-century Robin Hood figure.
The traditional Irish song Whiskey in the Jar tells the story of an Irish highwayman that robs an army Captain, and includes the lines "I first produced me pistol, then I drew me rapier. Said 'Stand and deliever, for you are a bold deceiver.'"
Adam and the Ants had a number one song for five weeks in 1981 in the UK with Stand and Deliver. The video featured Adam Ant as an English highwayman (see lyrics and video).

List of highwaymen

see List of highwaymen
Note: not all the criminals on the list are highwaymen.

Further reading

  • Ash, Russell (1970). Highwaymen, Shire Publications, ISBN 978-0852631010; revised edition (1994) ISBN 978-0747802600
  • Billett, Michael (1997). Highwaymen and Outlaws, Weidenfeld Military, ISBN 978-1854093189
  • Brandon, David (2004). Stand and Deliver! A History of Highway Robbery, Sutton Publishing, ISBN 978-0750935289
  • Dunford, Stephen (2000). The Irish Highwaymen, Merlin Publishing, ISBN 1-903582-02-4
  • Evans, Hilary & Mary (1997). Hero on a Stolen Horse: Highwayman and His Brothers-in-arms - The Bandit and the Bushranger, Muller, ISBN 978-0584103403
  • Haining, Peter (1991). The English Highwayman: A Legend Unmasked, Robert Hale, ISBN 978-0709044260
  • Harper, Charles George (1908). Half-hours with the Highwaymen: picturesque biographies and traditions of the "knights of the road", Chapman & Hall. Online edition, via Internet Archive.
  • Hobsbawm, Eric (1969). Bandits, Delacorte Press; Revised edition (2000). ISBN 978-1565846197
  • Koliopoulos, John S (1987). Brigands with a Cause, Brigandage and Irredentism in Modern Greece 1821-1912. Clarendon Press. ISBN 978-0198228639
  • Maxwell, Gordon S (1994). Highwayman's Heath: Story in Fact and Fiction of Hounslow Heath in Middlesex , Heritage Publications, Hounslow Leisure Services, ISBN 978-1899144006
  • Newark, Peter (1988). Crimson Book of Highwaymen, Olympic Marketing Corp, ISBN 978-9997354792
  • Pringle, Patrick (1951). Stand and Deliver: The Story of the Highwaymen, Museum Press, ASIN B0000CHVTK
  • Seal, Graham (1996). The Outlaw Legend: a cultural tradition in Britain, America and Australia, Cambridge University Press, ISBN 0-521-55317-2 (hbk), ISBN 0-521-55740-2 (pbk)
  • Sharpe, James (2005). Dick Turpin: The Myth of the English Highwayman, Profile Books, ISBN 978-1861974181
  • Spraggs, Gillian (2001). Outlaws and Highwaymen: The Cult of the Robber in England from the Middle Ages to the Nineteenth Century, Pimlico, ISBN 978-0712664790
wikisource The Highwayman
highwayman in Hungarian: Highwayman
highwayman in Dutch: Struikroverij
highwayman in Swedish: Stråtrövare
highwayman in Chinese: 拦路强盗
highwayman in German: Schnapphahn
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