
Picture a gangster. Are you thinking of Marlon Brando, smoking a cigar on the day of his daughter's wedding? Al Pacino mainlining cocaine in a Miami mansion? Hollywood has produced dozens of great gangster films, almost all starring men. But is this really art imitating life? Does the entire history of organised crime have a strong leading male, while the women sit in the background waiting for them to bring home the (stolen) bacon?
Unsurprisingly, the answer is no. Women have played a part in organised crime for centuries and, while many have been lost to history, some made such huge waves that we can't forget them. Across the world, women haven't just been gangsters, they've been leaders powerful enough to make you wonder: are Don Corleone and Tony Montana really the best Hollywood can come up with?
Click through to read their stories.

Stephanie St. Clair
Harlem's Unapologetic Queen of Crime
Stephanie St. Clair demanded to be known as "Queenie", and she lived up to the royal title. Moving to Harlem from the Caribbean in the early 20th century, Queenie used her tenacity and intellect to unequivocally RUN the neighbourhood during the Jazz Age.
She began as the head of an extortion gang but quickly earned a fortune by investing in shady schemes and playing the lottery. She never hid her activities, publishing ads about herself in the newspaper, and became known for dressing to the nines in jewels and sumptuous fur coats. She didn't keep her money to herself, either – she was a passionate civil rights activist, investing the savings of black New Yorkers, whom the banks shunned – and placed ads in the paper shaming police brutality, while advising her neighbours of their legal rights regarding segregation.
She also used these ads to throw shade at other gangsters trying to encroach on her territory, once telling readers that when she received death threats, "I just laugh at them, because such things sound silly to me". For the 1920s that was a serious burn and, after the Great Depression, gangsters like Dutch Shultz did all they could to kill Queenie and end her reign over Harlem's crime scene.
A gang war ensued which left 40 people dead and Queenie harassed by police, and eventually arrested. She took none of this lying down, getting police officers who worked against her fired by turning state witness about police corruption. Then, in 1935, she called a truce and began to retire from organised crime – but she never forgot those who disrespected her position. When her nemesis Dutch Shultz was fatally shot by Lucky Luciano on 23rd October 1935, Queenie sent a telegram to his bedside saying only, “As ye sow, so shall ye reap.” Exactly the dignified, stone-cold message you would expect from a killer queen.
Photo: Getty Images.
Bonnie Parker
America's Gun-Toting Sweetheart
You know Bonnie Parker, or at least you think you do. The gun-toting, cigar-smoking, star-crossed lover was immortalised by Faye Dunaway in 1967's Bonnie and Clyde, and has featured in countless couple's Halloween costumes ever since.
Clyde Barrow wasn't Bonnie's first bad boy, though. Born on 1st October 1910, Bonnie married her high school sweetheart in 1926, when she was just 16. She got their names tattooed on her upper thigh, then he got arrested and sent to jail for five years. Unsurprisingly, the tattoo outlasted the marriage and Bonnie was back living with her mother when she met ex-con Clyde in 1930. They immediately fell in love but just a few weeks later, Clyde was back in prison for stealing cars. Bonnie wasn't going to let the law deprive her of love a second time, though, and smuggled a gun into Clyde's prison to help him escape. This attempt didn't work – but Clyde's mother complaining to the judge did and by 1932 Bonnie and Clyde were reunited, to start their life together.
It was a life of crime. Bonnie joined Clyde's gang and they began a 21-month crime spree across Texas, Oklahoma and Missouri. By 1933 they were wanted for robbery and murder, including killing a police officer, but the public saw Bonnie as a Robin Hood figure. The Great Depression meant everyone hated the banks, and the gang's heists were seen as the little guy fighting back.
The discovery of the famous photographs of Bonnie and Clyde posing with their guns and cuddling next to stolen cars made them even more beloved. Young, beautiful and in love, Bonnie was simultaneously America's sweetheart and one of the FBI's most wanted women. In the end, it was the FBI that won out and on 23rd May 1934, Bonnie and Clyde were ambushed and killed by police.
Their funerals were attended by thousands, and papers even published poetry Bonnie had written while Clyde was in jail: "Some day they'll go down together / And they'll bury them side by side / To few it'll be grief / to the law a relief / but it's death for Bonnie and Clyde."
Photo: Getty Images
Zheng Yi Sao
The World's Smartest Pirate Leader
So little is known about Zheng Yi Sao as a woman that we don't even know her birth year or her real name (Zheng Yi Sao means "Zheng Yi's wife"). Those who do know her, know her as a legend who brought the Chinese government to its knees in less than a decade and commanded the fiercest criminal network of the day.
In 1801, Zheng Yi Sao was working in a brothel in Canton when the chief of a local pirate fleet offered to marry her. She agreed, on the condition that she would be an equal partner and rule the pirate fleet with him. Proving this early version of a pre-nup to be an exceptionally good move, Zheng Yi Sao spent six years building up her husband's Red Flag Fleet, stashing booty and terrorising the high seas.
In 1807, when her husband died, Zheng Yi Sao refused to step aside. She knew her pirates needed a man (nominally) in charge so named her second-in-command captain while she focussed on strategy and business. Turns out, she was a dab hand at the latter.
Eventually, her pirate fleet rivalled the navies of some countries, she had a spy network across land and sea, and made a fortune from extortion and protection schemes. She also demanded those in her criminal network live by a set of strict rules; anyone who disobeyed an order was beheaded. Captives were treated with respect and any pirate who sexually assaulted a woman was immediately killed.
By 1810, just nine years into her criminal career, Zheng Yi Sao's organisation was so powerful that the Chinese government knew it couldn't fight her. Instead, she was offered amnesty and Zheng Yi Sao, being the excellent tactician that she was, negotiated a deal to keep all her money. She married her former second-in-command, opened a respectable casino and died peacefully in 1844, surrounded by her grandchildren. A wealthy woman who was once the most successful organised criminal in China and perhaps the greatest pirate the world has ever known.

Fredericka Mandelbaum
New York's Rags-to-Riches Criminal Mastermind
In 1850, 23-year-old Fredericka Mandelbaum took a boat from Prussia to begin a new life with her husband in New York City. Incredibly poor, living in a tenement and scratching out a life as peddlers, the Mandelbaums looked destined for a life of poverty. If Fredericka hadn't been Fredericka, that is.
In 1857, New York's financial system collapsed and more people than ever were plunged into poverty. Fredericka was determined to save her family in any way possible – so she became a criminal, training the desperately poor people around her, many of them children, to become pickpockets and thieves. Fredericka resold everything they stole and became one of the most prolific fences in New York City. By 1865, her business was so successful that she and her husband bought an entire shop for storing their stolen goods and to act as a front for their illegal activities.
Though her husband's name was on the lease, he was reportedly too meek to really help Fredericka. She was the powerhouse. By 1887, even New York's former chief of police, George W. Walling was calling her "a wonderful person... as adept in her business as the best stock-broker in Wall Street in his. " Her business grew as she became known in the city's synagogues and bars, eventually making friends in law enforcement and being courted by politicians for her influence in the Jewish community.
Generally, her friends were far less respectable, however. She built up a criminal network that would have made Tony Soprano weep, even founding a school to train criminals in the art of theft. Lamenting that most women were "wasting life being housekeepers", she taught many, including her own daughters, to support themselves through illegal activity. She was generous to her employees, too, setting up a fund to pay all their bail and legal fees.
Eventually, this criminal empire grew too big to slip under the radar. On 16th September 1884, The New York Times reported the arrest of "Mme Fredericka Mandelbaum the notorious fence " after a private detective infiltrated her network. When her troves of stolen goods were finally found, full of jewels, antiques and precious metals, it was clear that even her expensive legal counsel wouldn't be able to get her off the charges.
But she wasn't going to jail. On 5th December 1884, Fredericka jumped bail and fled to Canada. Though she lived in affluent freedom for the rest of her life, she was said to long for New York and when she died, in February 1894, her body was brought to her beloved home and laid to rest in Queens at her request. Her legacy clearly lived on: several mourners at her grave reported having been pickpocketed during the funeral.

Alice Diamond
London's Gangland Girl Boss
Before Taylor Swift's bevy of uber-talented female friends took over the planet, there was only one girl gang: The Forty Elephants. There's evidence that this all-female gang may have existed in some form since the late 1700s but they became truly notorious in 1916, when 20-year-old Alice Diamond became their "Queen".
Alice became such an accomplished criminal leader that the police themselves eventually called her "the cleverest of thieves ". She set up a code of conduct for her gang members, with rules like staying sober the night before a job, not wearing stolen goods and not giving away other gang members if they were arrested. Her network of cells was so strong that female criminals had control across London – she then sent them lists of high-end targets to rob or shoplift from, taking a cut from each job.
Soon they were one of the most powerful criminal networks in London, and Alice made sure they moved with the times. During the Edwardian era, when women's bodies were seen as shameful, the gang took advantage of shopkeepers' prudishness to hide stolen goods underneath their skirts. She would also give her girls false credentials to get jobs as housemaids in aristocratic houses, only to have them spirit away their new employers' valuables in the night.
When the Roaring Twenties rolled around, their skirts got shorter and instead they used their new, fast cars to outrun police. They also extorted money from men who tried to seduce them, who paid to make sure The Forty Elephants didn't tell their wives. They were known for their raucous parties, living the life of Hollywood movie stars, dressed in jewels and furs in London's restaurants and clubs. The newspapers loved to report on these glamorous criminals, so much so that the police had to ask journalists in America and the UK to stop giving them publicity.
The police had little power over The Forty Elephants, though. Gang member Ada Wellman was arrested in 1921 for stealing on behalf of Alice Diamond but remained a member of The Forty Elephants in 1939. Alice herself was convicted for an attack on a rival gang in 1925, but continued running things from behind bars. The only time the police had the upper hand was in 1923, when gang member Maggie Hughes ran from a jeweller's shop carrying a tray of 34 diamond rings straight into a policeman, who happened to be outside.
Despite Alice's ferocity and determination, the age of flappers and ganglands was coming to an end. When Britain entered World War Two, The Forty Elephants slipped from the headlines and London forgot its gangland queen. Keep an eye on your Netflix queue, though: the BBC is rumoured to be developing a series around Alice and her gang of female criminals. A show about fast cars, jewels and strong women? We think Alice would approve.

Gertrude "Cleo" Lythgoe
The Mysterious Rum Runner of the Bahamas
Like everything about Gertrude "Cleo" Lythgoe, her legacy is mysterious, romantic and beguiling. Known today as possibly the greatest female rum runner during Prohibition, in her day "Cleo", as she preferred to be known, entranced the bootlegging set with her beauty and extravagant exoticism.
Leaving her job as a secretary for a life of adventure, Lythgoe is said to have spent three years as "Queen of the Booze Buccaneers of the Bahamas ". She is said to have used her charms to illegally import rum from the Bahamas into the United States, keeping flappers flapping and fuelling late-night jazz parties.
Like most bootleggers of the time, it didn't pay to advertise, so most of what we know comes from Caribbean whispers and boozy stories. There are tales that after she sold all her liquor in New York, she boarded a speedboat to Long Island before jumping into a cab straight to the Waldorf Astoria to live the high life. More substantive sources have her spending a summer with the infamous rum runner Bill McCoy, after sexist smugglers in Nassau forced her out.
Sadly the only real proof we have of the elusive Cleo is when the party finally ended. In October 1925, newspapers reported the arrest of Gertrude Lythgoe. By that time, though, she had already retired from rum running – it was only when she slowed down that the "secret service" was able to catch up with her. She kept up her air of mystery, however, seemingly escaping jail time and fading into retirement, leaving only the legend of the greatest female rum runner ever to sail the seas – and, we imagine, many hangovers – in her wake.
Like what you see? How about some more R29 goodness, right here?
A Week In Chicago, IL, On A $75,000 Salary
A Week In Chicago, IL, On A $65,000 Salary
You Can Now See How Much Time You Spend On Instagram, But Do You Want To Know?