Buzz
"Some of the most remarkable literary works were crafted within prison walls," observed Raoul Duke in Hunter S. Thompson’s Fear and Loathing in Las Vegas. This sentiment rings true, as luminaries like Gandhi, Malcolm X, Nelson Mandela, the Marquis De Sade, and O. Henry transformed their time behind bars into profound written legacies.
However, these individuals were already writers at heart. Each person on this list began their journey as a hardened criminal—not a political activist, intellectual, or dissident, but someone capable of extreme violence without hesitation. What makes their stories extraordinary isn’t merely their ability to pen books, but their capacity for personal transformation, leaving behind their brutal histories and liberating their minds through creative expression.
10. Edward Bunker
Edward Bunker appeared in several films, such as The Longest Yard, Tango & Cash, and Animal Factory, but he is most recognizable as Mr. Blue from Reservoir Dogs. Despite having minimal screen time and dialogue—even dying offscreen—Bunker’s real-life background suggests that, if the movie were real, he alone could have pulled off the robbery.
Bunker’s criminal career began shockingly early. At three, he smashed his neighbor’s generator with a hammer, and at four, he set their garage on fire. By 15, he stabbed someone in the eye with a fork—hopefully not the same neighbor. His crimes grew increasingly severe, leading to his incarceration in Los Angeles County Jail at 17, where he stabbed a guard and escaped. He was later sent to San Quentin, becoming its youngest inmate.
While in solitary confinement near Caryl Chessman, a notorious killer and published writer, Bunker discovered a passion for storytelling. Over 18 years, his criminal escapades escalated both inside and outside prison, including FBI pursuits and faking insanity. By the late 1960s, he was in Folsom Prison, still honing his writing. After 12 rejections, he published No Beast So Fierce, which was adapted into the 1978 film Straight Time, starring Dustin Hoffman as a character inspired by Bunker. Bunker also landed a minor role in the movie.
Bunker went on to write multiple bestsellers, produce films, and act in various roles. Quentin Tarantino, who watched Straight Time while working at a video store, cited it as a major influence on Reservoir Dogs and even consulted Bunker during production. Bunker’s life of crime reads like a Batman villain’s backstory, and in a Reservoir Dogs featurette, he recounts his wildest exploits, sounding like the most intimidating grandfather imaginable.
9. Mark ‘Chopper’ Read
Mark “Chopper” Read was born in Melbourne, Australia, and spent his early years in a children’s home. By 14, he became a ward of the state and was sent to a psychiatric hospital, where he underwent electroshock therapy. The harsh treatment failed to reform him, and by his late teens, he had risen to lead his own criminal gang.
Read had a revelation: targeting drug dealers for theft ensured a steady stream of cash-rich victims who couldn’t involve the police. Similar to Omar from HBO’s The Wire, he became a notorious figure in the criminal underworld. Despite his claims of never harming innocents, his methods were notoriously violent—he once admitted to using bolt cutters to sever rivals’ toes.
However, the judge he kidnapped at gunpoint in 1990 might dispute his self-proclaimed moral code. Read took the judge hostage in a misguided attempt to secure the release of a gang member, but the plan backfired, landing him in prison instead.
During his incarceration, Read became embroiled in a prison conflict. To secure a transfer, he persuaded another inmate to cut off his ears. While the transfer succeeded, he was later stabbed multiple times, losing significant portions of his intestines. He later claimed this gruesome incident earned him the nickname “Chopper.”
While recovering, a journalist’s inaccurate report about one of his crimes prompted Read to share his own stories. These accounts formed the foundation of his first book, which became a massive success, briefly making him Australia’s best-selling author. His work even garnered praise from legendary crime writer Elmore Leonard. Read later ventured into stand-up comedy, inspired a film starring Eric Bana, created a PSA condemning domestic abuse, and briefly pursued a rap career.
The authenticity of Chopper’s books remains debatable—were they entirely factual or filled with exaggerated, fictionalized tales? Chopper was a master of self-promotion and theatrics, often dismissing his past claims as “just jokes.” The boundary between truth and fiction frequently blurred in his narratives. For instance, in the interview above, he famously brandishes a loaded gun at a reporter, coercing her into a game of Russian roulette.
8. Jimmy Boyle
In 1967, Glasgow gangster Jimmy Boyle was hiding in London under the protection of the notorious Kray twins. However, undercover police cornered and arrested him for the murder of fellow gangster Babs Rooney. Boyle, previously arrested twice for murder but never convicted, insisted he was innocent of Rooney’s killing. He claimed the actual murderer was a close friend, and he refused to betray him by “grassing” (snitching). Despite his protests, he was convicted and sentenced to life imprisonment.
After multiple clashes with prison authorities, Boyle was transferred to a unique unit at Barlinnie Prison in Scotland in 1973. This experimental unit, established by a senior prison officer and a civil servant, aimed to transform the rehabilitation of violent offenders. Inmates were granted democratic input into the unit’s operations and encouraged to pursue artistic endeavors, with access to teachers, books, and art supplies.
In 1977, Boyle penned his debut book, Sense Of Freedom, a semi-autobiographical novel exploring his tough childhood in Glasgow, his early criminal activities, and his eventual redemption through art and literature while incarcerated. Though the book doesn’t romanticize Boyle’s life, it sparked significant controversy, with The Sun later labeling him “Scotland’s Most Notorious Murderer.”
Three years after the novel’s publication, Boyle married a psychiatrist who sought him out after reading his work. Paroled in 1982, he has stayed out of prison ever since. Today, Boyle is a celebrated novelist and sculptor, with his artworks fetching around £10,000 each as of 1999.
7. Chester Himes
Born in 1909 into a middle-class African American family, Chester Himes’s life took a dark turn after his younger brother was blinded in an accident. The family’s decline pushed Himes toward a lifestyle of crime, alcohol, and prostitution. He dropped out of college following an incident involving a fraternity trip to a brothel, leading to his arrest in 1928. By 19, his criminal record included check fraud, armed robbery, and an attempt to steal weapons from the National Guard.
During his time in prison, Himes started writing short stories, some of which were published in black interest magazines. This success encouraged him to submit his work to national publications—a daunting challenge for an African American man in the 1930s. In 1934, he achieved a significant milestone when Esquire published his work, credited simply as “Prisoner Number 59623,” a remarkable feat in the era before the Civil Rights Movement.
Despite receiving a 20- to 25-year sentence, Himes was released in 1936, likely due to good behavior. He went on to publish a series of novels, initially focusing on protest literature addressing racial issues in the US. Later, he moved to Paris, where he spent the remainder of his life crafting surreal noir detective fiction. His contributions earned him the Grand Prix de Litterature Policiere, making him the first African American writer from the US to receive France’s most prestigious award for crime and detective fiction.
6. Robert ‘Iceberg Slim’ Beck
Born Robert Lee Maupin in Chicago in 1918, “Iceberg Slim” grew up in a middle-class household thanks to his hardworking single mother. Despite her efforts, Robert was drawn to crime from a young age. To steer him away from trouble, his mother enrolled him at the Tuskegee Institute (now Tuskegee University) in the 1930s, where he briefly crossed paths with future author Ralph Ellison. However, Robert was expelled for gambling and, by 18, had turned to pimping as a way of life.
Robert claimed the nickname “Iceberg Slim” originated from a bar shoot-out where he calmly sipped whisky on the rocks. In reality, he adopted the moniker himself to enhance his larger-than-life persona.
After numerous stints in various prisons, he began to immerse himself in reading and writing. A prolonged period in solitary confinement at the Cook County House of Corrections in 1960 made him realize he was too old for the pimping lifestyle. Upon his release, he relocated to California, changed his name to Robert Beck, and started documenting his life experiences. This led to the publication of his 1967 autobiographical novel, Pimp: The Story of My Life.
He went on to write several more novels, produce spoken-word albums, and publish essays. By 1971, his books had sold over two million copies, and one of them, Trick Baby, was adapted into a film in 1972. Despite his success, he received minimal royalties from his publisher.
Beck’s influence extended deeply into music, film, and literature. Ice-T and Ice Cube both drew inspiration from his name. Irvine Welsh, a devoted fan, once remarked, “If I hadn’t picked up Pimp, I doubt I could have written Trainspotting or Glue.”
5. Robert E. Burns
In 1919, Robert Elliot Burns came back from World War I shattered. While he was away fighting in Europe, his fiancée married another man, his job was taken, and the only work he could find paid far less than before. The war’s trauma left him with severe shell shock, and with little support from the government or military, Burns soon became a penniless drifter.
Three years later, Burns and two other vagrants were arrested for robbing a Georgia grocery store. Burns was sentenced to six to ten years of hard labor on a chain gang.
The robbery had earned him a mere $5.80.
Life on the chain gang was harsh and dehumanizing, with frequent escape attempts despite the high risk of being shot or hunted down by bloodhounds. One day, Burns seized an opportunity to escape. He convinced a fellow inmate to weaken his ankle chains with a sledgehammer, allowing him to break free. Against all odds, he evaded both the bloodhounds and armed search parties.
Burns found freedom and, for a time, thrived. He settled in Chicago, got married, and even launched a successful magazine called Greater Chicago. However, in 1929, his life took a turn when he fell out of love with his wife and sought a divorce. Having previously confided in her about his fugitive past, she retaliated by reporting him to the authorities.
Thanks to Burns’s prominent status in Chicago, a group of civic leaders rallied to prevent his extradition. Initially, it appeared their efforts would succeed, as Georgian officials assured Burns he wouldn’t face another chain gang if he returned, instead serving 60 days of supervised office work. However, upon his arrival in Georgia, he was immediately shackled and sent back to a chain gang.
Fortunately, Burns escaped a second time by persuading a farmer to let him hide in his truck. Once again, he evaded capture, fleeing to Tennessee.
In 1931, Burns submitted a series of gripping stories to True Detective magazine titled “I Am a Fugitive From a Chain Gang.” These stories became immensely popular, drawing the attention of Hollywood. Burns secretly worked as a consultant and acting coach on the film adaptation of his life. He remained in hiding for another 13 years until his sentence was commuted in 1945. The film’s success sparked widespread outrage against the chain gang system, leading to its abolition by 1955.
4. Noel ‘Razor’ Smith
Noel “Razor” Smith’s criminal journey began modestly with the theft of apples as a child. He claims this incident, coupled with police provocation, pushed him toward more serious crimes. By 16, he was sentenced to three years in prison for armed robbery.
Noel’s time in prison did little to reform him; instead, he mingled with seasoned criminals and built connections within London’s underworld. After his release, he committed over 200 bank robberies.
During one of his many incarcerations, he spent nine months in solitary confinement. To combat boredom, he taught himself to read and write, discovering a knack for storytelling. He entered a short story competition and, to everyone’s astonishment, won first place. This victory inspired him to pursue writing more seriously. Using his prize money, he bought a typewriter and began drafting his autobiography.
Released again in 1997, he coincidentally met renowned author Will Self. The two struck up a friendship, and when Smith was imprisoned once more, he sent his writings to Self for critique. Self’s advice was straightforward: his work was promising, but he’d never succeed if he kept getting arrested.
After the tragic loss of his son, Smith heeded Self’s advice, realizing that “there’s no glamour in crime.” Despite being labeled “below average intelligence” by the prison system, he completed his debut novel, A Few Kind Words and a Loaded Gun, published in 2004 to largely positive reviews. The book concluded with a real-life incident that landed him back in prison: while working as a road sweeper, he assaulted a man who dumped his ashtray on a freshly cleaned spot. “I dropped my broom and hit him hard with three punches... He was still squealing, so I kicked him in the bollocks.”
Smith was serving a life sentence for bank robbery and illegal firearm possession when his novel was released. His prison record was far from exemplary, with at least 58 convictions, including aggravated violence against guards, inciting riots, crafting makeshift weapons, and escape attempts. Despite this, he committed to earning parole, maintained a low profile, and continued writing.
In 2010, he was finally released for the last time. After 33 years of being incarcerated or evading capture, he secured a position as an assistant editor at Inside Time. Since then, he has not committed any further offenses.
3. Henri Charriere
In 1931, a skilled safecracker was arrested and found guilty of murdering a gangster from Monte Marte. While Henri Charriere acknowledged his criminal past, he insisted that he was wrongly accused in this case, blaming “dishonest informers.” Despite his claims, he was sentenced to a penal colony in French Guiana known as Cayenne. The conditions there were brutal, and after three years, Charriere managed to escape. He briefly took refuge in a leper colony before sailing on a fragile boat to the Gulf of Venezuela, where he lived with indigenous islanders until his recapture and transfer to the infamous Devil’s Island.
To prevent another escape, authorities confined Charriere to solitary for three years. This only fueled his determination to break free, leading to eight more escape attempts over the years. His eighth attempt succeeded. Using a raft made of coconut husks, he navigated shark-filled waters surrounding the island. He then spent several years in hiding in Venezuela.
Inspired by Albertine Sar Razin’s autobiography about her criminal life, Charriere decided to pen his own story. His book, Papillon, achieved massive success and was later adapted into a film featuring Steve McQueen and Dustin Hoffman. However, some critics argue that Charriere may have exaggerated his tale or blended it with stories of fellow inmates. In 2005, Charles Brunier, a 105-year-old nursing home resident, claimed to be the true Papillon, asserting he had been imprisoned alongside Charriere.
Regardless of whether his story is an autobiography, a semi-fictional account, or entirely made up, it remains a captivating read that transformed Charriere’s life and continues to intrigue readers.
2. Chicago May—The Queen of Crooks
Born in 1871 to a struggling family in County Longford, Ireland, May Duignan embarked on a life of crime at 19 by stealing her family’s savings to fund her journey to the United States. From there, she became a globe-trotting criminal, engaging in activities described in Frank Colomb’s book Chicago May—Queen of the Blackmailers as “swindles, betrayal, conspiracy, and revenge,” alongside acts of “assault, cruelty, robbery, and attempted murder.” She was also a pioneer in using photographs for blackmail, earning her the infamous title “The Queen of Crooks.”
May was involved in numerous crimes, arrests, and acquittals, including a major heist that stole over $250,000 from the American Express office in Paris. She and her then-boyfriend were eventually caught. He received a life sentence on Devil’s Island, while she was given five years in Montpellier. However, after seducing and blackmailing the prison doctor, May secured an early release. In 1907, her ex-boyfriend escaped, tracked her to London, and accused her of betraying him. This led to her arrest again, this time for her role in a shootout involving her, her ex, and her new lover.
May’s notorious exploits earned her headlines in London newspapers, branding her as the most dangerous individual in London, Europe, and the world. Decades later, at 56, she was found ill and shackled to a prison bed by August Ames, a prison reformer. Ames encouraged her to write a book about her life. May, though not a professional writer, persevered. Her book was published in 1928, but she passed away in poverty the following year.
1. Howard ‘Mr. Nice’ Marks
Born in Bridgend, South Wales, in 1945, Howard Marks began smoking cannabis while studying at Oxford University in the late 1960s. Despite earning a degree in nuclear physics, he chose a different path, becoming a cannabis smuggler. He quickly rose to prominence, collaborating with the American Mafia, the IRA, and MI6.
Marks initially believed his smuggling career would be short-lived, assuming marijuana would soon be legalized and taxed. Using his education, he devised clever methods to transport large quantities of cannabis across borders. Some of his most ingenious plans included concealing 30 tons of marijuana in the ballast of salvage ships and forming a fake band to smuggle drugs in musical equipment. His operation grew so vast that it required 89 phone lines to manage.
Soon, the CIA began to take notice of him.
As law enforcement closed in, Marks managed to stay one step ahead. After facing drug charges in Nevada in 1976, he disappeared, only to resurface unexpectedly on a London stage in 1979, surrounded by Elvis impersonators. He was apprehended again in 1980 in the Scottish Highlands. Despite being caught with $30 million worth of marijuana, he avoided conviction by cleverly claiming in court that he had been working for MI6. While he had previously collaborated with MI6, this particular claim was false. Nonetheless, the resulting confusion and embarrassment for the British government led to his acquittal.
Ultimately, the DEA located Marks in his Spanish hideout. He was arrested, extradited, and sentenced to 25 years in Terre Haute, Indiana. After serving seven years, he was paroled and penned his autobiography, Mr. Nice, named after one of his many aliases.
The book propelled Marks to fame, and he became a columnist for Loaded magazine in 1996. He featured in the Super Furry Animals song “Hangin’ with Howard Marks,” made a cameo in the 1999 film Human Traffic, and even ran for political office in 1997 on a platform advocating marijuana legalization.
His autobiography sold millions of copies and was adapted into a film in 2010. Marks spent years advocating for marijuana legalization. While he witnessed its decriminalization in several U.S. states, no such reforms occurred in his home country, Britain. He once quipped, “After my ordeal with the U.S. legal system, I never expected America to be at the forefront of this change.”
In early 2015, Marks revealed that he had been diagnosed with bowel cancer, which was deemed inoperable. Tragically, he passed away in 2016.
