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A highwayman was a thief and brigand who preyed on travellers. This type of outlaw usually travelled and robbed by horse, as compared to a footpad who travelled and robbed on foot. Mounted robbers were widely considered to be socially superior to footpads. Such robbers operated in Great Britain (British colonies as well) and Australia from the Elizabethan era until the early 19th century.
The word highwayman is first known to be used in the year 1617; other euphemisms included "knights of the road" and "gentlemen of the road". In the 19th-century American West, highwaymen were known as road agents. In the same time period in Australia, they were known as bushrangers.
Some robbed individually, but others worked in pairs or in small gangs. They often attacked coaches for their lack of protection, including public stagecoaches; the postboys 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!" "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 surrendered.—The Proceedings of the Old Bailey, 25 April 1677, 
The phrase "Your money or your life" is mentioned in trial reports from the mid-18th 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, 
There is a long history of treating highway robbers as heroes. Originally they were admired by many as 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 French-born gentleman highwayman Claude Du Vall, John Nevison, Dick Turpin, Sixteen String Jack, the Slovak Juraj Jánošík, and quite a few Indians, including Kayamkulam Kochunni, Veerappan and Phoolan Devi.
In 17th- through 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, bandits who harassed the British were known as tories (from Irish tórai, raider). Later in the century, they became known as rapparee. Famous highwaymen included James Freney, Willy Brennan, and Jeremiah Grant.
Highwaymen often laid 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, England. 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 (Great Britain), was very nearly as bad. Many other places could be mentioned.
During the late 17th and early 18th centuries, highwaymen in Hyde Park, were sufficiently common for King William III to have the route between St. James's Palace and Kensington Palace (Rotten Row) lit at night with oil lamps, as a precaution against them. This made it the first artificially lit highway in Britain.
The penalty for robbery with violence was hanging, and most notorious English highwaymen ended on the gallows. The chief place of execution for London and Middlesex was Tyburn Tree. Famous highwaymen whose lives ended there include Claude Du Vall, James MacLaine, and Sixteen-string Jack. Highwaymen who went 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.
In England, after about 1815, mounted robbers are recorded only rarely. The last recorded robbery by a mounted highwayman occurred in 1831. The decline in highwayman activity occurred during the period in which repeating handguns, notably the pepperbox and the percussion revolver, became increasingly available and affordable to the average citizen. 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. Enclosure, and with it the decline in undeveloped open fields and increase in private incentives to regulate trespassers, may also have played a role.
Tradition identifies Saint Dismas, or the Penitent Thief, as a highwayman. Crucified with Jesus Christ, he repented of his sins and was told by Jesus, "This day you shall be with Me, together in paradise."
The bandits in Greece under Ottoman rule were the Klephts (κλέφτες), Greeks who had taken refuge in the inaccessible mountains. The klephts, who acted as a guerilla force, were instrumental in the Greek War of Independence.
The highwaymen of 18th- and 19th-century Kingdom of Hungary were the betyárs. Until the 1830s they were mainly simply regarded as criminals but an increasing public appetite for betyar songs, ballads and stories gradually gave a romantic image to these armed and usually mounted robbers. Several of the betyárs have become legendary figures who in the public mind fought for social justice. The most famous Hungarian betyárs were Sándor Rózsa, Jóska Sobri, Márton Vidróczki, Jóska Savanyú. Slovakia's Juraj Jánošík (Hungarian: György Jánosik) is still regarded as the Slovakian Robin Hood.
The Indian Subcontinent has had a long and colorful history of organised robbery for millennia. Most famous of these were the Thuggees, a quasi-religious group that robbed travellers on Indian roads until the cult was systematically eradicated in the mid-1800s by British colonial administrators. Thugees would befriend large road caravans, gain their confidence, strangle them to death at the right moment, and then rob them of their valuables. According to some estimates the Thuggees murdered 1 million people between 1740 and 1840. More generally, armed bands known colloquially as "dacoits" have long wreaked havoc on many parts of the country. In recent times this has often served as a way to fund various regional and political insurgencies that includes the Maoist Naxalite movement.
The bandits in Serbia, Bosnia and Croatia under Ottoman rule were the Hajduks (Hajduci, Хајдуци), rebels who opposed Ottoman rule and acted as a guerilla force, also instrumental in the many wars against the Ottomans and especially the Serbian revolution. Serbian and Croatian refugees in Austro-Hungarian (and Habsburg) lands were also part of the Uskoci. Notable freedom fighters include Starina Novak, a notable outlaw was Jovo Stanisavljević Čaruga.
In Shakespeare's Henry IV, Part 1 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 legend of Dick Turpin owes an enormous amount to 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.
From the early 18th century, collections of short stories 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 The Newgate Calendar in their titles and this has become a general name for this kind of publication.
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.
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.
The traditional Irish song "Whiskey in the Jar" tells the story of an Irish highwayman who robs an army captain, and includes the lines "I first produced me pistol, then I drew me rapier. Said 'Stand and deliver, for you are a bold deceiver'."
The traditional Irish song "The Newry Highwayman" recounts the deeds and death of a highwayman who robbed "the lords and ladies bright".
The contemporary folk song "On the Road to Fairfax County" by David Massengill, recorded by The Roches and by Joan Baez, recounts a romantic encounter between a highwayman and his female victim. In the end, the highwayman is hanged over the objections of his victim.
Musician Jimmy Webb penned and recorded a song entitled Highwayman in 1977 about a soul with incarnations in four different places in time and history, a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a star ship captain. Glen Campbell recorded a version of the song in 1978, but the most popular incarnation of the song was recorded by Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash in 1984, who as a group called themselves The Highwaymen.
The Carry On films included a highwayman spoof in Carry On Dick (1974). Monty Python sent up the highwayman legends in the Dennis Moore sketch in Episode 37 of Monty Python's Flying Circus, in which John Cleese played the titular criminal who stole only lupins. In Blackadder the Third, Mr. E. 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. Additionally the actor Mathew Baynton played Dick Turpin in Horrible Histories.
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 and 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 Fable II, Highwaymen appear as an elite type of enemy which works alongside bandits and makes use of speed and agility over brute strength. It is also possible for players to dress as Highwaymen. There is an enemy type in The Elder Scrolls V: Skyrim called the "bandit highwayman" that acts as one of the higher-level bandit enemies. In World of Warcraft one can encounter the Defias Highwaymen, the strongest members of the Defias Brotherhood.
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