Masked bandits, resistance fighters, highwaymen, and downright criminals: Discover the thrilling stories behind history's greatest outlaws

Masked bandits, resistance fighters, highwaymen, and downright criminals: Discover the thrilling stories behind history's greatest outlaws

From the lawless Wild West to the tyrannic Scottish Highlands, Graeme Green uncovers the stories behind some of the most fabled and mysterious outlaws in history


Robin Hood

Arguably the world’s most famous outlaw, Robin Hood famously stole from the rich to give to the poor in Sherwood Forest with his band of Merry Men (Little John, Friar Tuck and co) and women (Maid Marian). But just who was Robin Hood? Was he real, or a fictional creation? “These are questions scholars and others have been trying to answer for decades - centuries even,” says Dr. Lesley Coote, author of Storyworlds of Robin Hood.

“There have been lots of different ‘answers’, but nothing has been convincingly proven. A large time gap exists between the earliest written story that still exists (the 1460s) and the earliest time when Robin Hood might have lived (the 1190s). The most plausible candidate now is one Robert of Wetherby, who may or may not have been the Robert of Wetherby, who was pursued, caught and executed by agents of Eustace of Lowdham, then Sheriff of Yorkshire in 1225.

Even if there was a real-life inspiration, the Robin Hood the public knows today is a figure of fiction, appearing in English ballads from the late 1300s and into the 1400s, and continuing to be a major figure in popular culture in modern times, with Errol Flynn, Kevin Costner and Russell Crowe just three Hollywood greats to play Hood on the big screen. Another movie icon, Hugh Jackman, is set to play Robin in The Death of Robin Hood this summer.

William Wallace

William Wallace, known as ‘the Guardian of Scotland’, was a knight and leader born around 1270. He’s famous for leading the Scottish resistance against English rule during the wars of Scottish Independence. Like Robin Hood, he’s a symbol of freedom, courage, patriotism and defiance against tyranny. While based on a real historical figure, his exploits were often romanticized, particularly in medieval chronicles. Mel Gibson played fast and loose with the facts in Braveheart (1995), which he directed, as well as starred in, the film, which is famous, not least, for his cry of “Freeeeedooooommmm!!!”.

Rob Roy

Rob Roy was a Scottish outlaw, folk hero, Jacobite supporter and clan leader active in the Scottish Highlands in the late 1600s and early 1700s. Known as ‘The Highland Robin Hood’, he had a reputation for protecting the poor and resisting oppressive landlords. He’s famous for cattle raiding, defying English authority, and his role in Scottish clan conflicts. Again, he was a real person, with legends originating in 18th-century Scottish ballads and oral tradition. Liam Neeson played him in Rob Roy (1995), which came out in the same year as Braveheart.

24th November 1937: A man collecting money for Hounslow Hospital, dressed up as highwayman Dick Turpin, holds up a motorist in Hounslow to demand a contribution. (Photo by Harry Todd/Fox Photos/Getty Images)
Taken on 24th November 1937: A man collects money for Hounslow Hospital, dressed up as highwayman Dick Turpin, holding up a motorist in Hounslow to demand a contribution. (Credit: Harry Todd/Fox Photos/Getty Images)

Dick Turpin

Dick Turpin was an English highwayman believed to be active in the early 18th century, primarily around London and Essex. Known for daring robberies and horsemanship, he’s often presented as a gallant outlaw who robbed the rich, though in reality, he was a thuggish criminal with violent and murderous tendencies.

The Turpin legend grew in England through novels and newspapers in the 18th and 19th centuries. Screen versions, such as Dick Turpin: Highwayman (1951) and the 1979 British TV series Dick Turpin, played up the romanticized version, with The Mighty Boosh’s Noel Fielding giving it a comedic spin in 2024 series The Completely Made-Up Adventures of Dick Turpin.

Butch Cassidy

Butch Cassidy was an American outlaw operating in Utah and Wyoming in the late 19th century, known for leading the Wild Bunch gang in bank and train robberies, often featuring clever plans and daring escapes. Another real person, stories of the American West romanticise him as a charming, gentlemanly, anti-authority figure, often paired up with the Sundance Kid. It doesn’t hurt your reputation at all to have Paul Newman play you, as he did (opposite Robert Redford) in the classic western Butch Cassidy and the Sundance Kid (1969). Other legendary outlaw figures from the American West include Jesse James, Billy the Kid and Calamity Jane.

Actors Bob Hope as 'Painless' Peter Potter and Jane Russell as 'Calamity Jane' in the Western 'The Paleface', 1948. (Photo by Silver Screen Collection/Getty Images)
Actors Bob Hope as 'Painless' Peter Potter and Jane Russell as 'Calamity Jane' in the Western 'The Paleface', 1948. (Credit: Silver Screen Collection/Getty Images)

Calamity Jane

Calamity Jane, aka Martha Jane Cannary, also lived in the American West, including South Dakota, where she became famous as a frontierswoman, scout and storyteller, known for her sharpshooting skills and tough demeanour. She was based on a real person, with legends of her exploits circulated in the United States during the late 19th and early 20th centuries. Popular myths romanticize her as a fearless, independent woman, who often dressed in men’s clothing. Doris Day famously played her in Calamity Jane (1953).

Phoolan Devi

Phoolan Devi, known as ‘The Bandit Queen’, was born in 1963 in Uttar Pradesh, India. She became notorious for leading a gang of bandits in the Chambal region, exacting revenge against upper-caste men for social injustices and violent personal attacks against her. A real person, she later became a politician, serving as a Member of Parliament. The myths frame her as a Robin Hood figure and a fearsome outlaw, highlighting issues of class, gender and oppression in rural India. Seema Biswas played her in Shekhar Kapur’s biopic Bandit Queen (1994).

Zorro

Zorro, aka Don Diego de la Vega, is a fictional masked vigilante who operated in Spanish California in the late 1700s and early 1800s. Clever, heroic and charismatic, he also defended the oppressed, using his sword and horsemanship skills, often leaving behind his signature Z mark. The character was created by Johnston McCulley in 1919, originating in American pulp literature. Antonio Banderas took the title role in The Mask of Zorro (1998), opposite Catherine Zeta Jones, with Tyrone Power starring in the earlier The Mark of Zorro (1940).

Top image: American actor and producer Douglas Fairbanks Sr., actors Marguerite De La Motte and Robert McKim on the set of The Mark of Zorro, directed by Fred Niblo. (Credit: Twentieth Century Fox Pictures/Getty Images)

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