John Mitchinson explores a surprisingly modern role model from the backstreets of Jacobean London

Sign up for our weekly Behind the Headlines email and get a free copy of Byline Times posted to you

Like much else in contemporary life, the debates about sex and gender aren’t quite as new and radical as they first appear. 

In the London of the early 17th Century, one of the most famous and controversial celebrities was born a woman but lived as a man.

Mary Frith, better known as Moll Cutpurse, started out as a pickpocket but soon developed grander ambitions. By 1608, she was performing in the streets and taverns of Southwark. Dressed in a doublet and leather jerkin, a sword hanging by her side and a pipe clamped between her teeth, she would strum her lute, sing rude songs, dance jigs and tell saucy stories. ‘Moll Cutpurse’ became an overnight sensation. More like a contemporary conceptual artist than the actors she hung round with, not only did she perform as a man, she lived like one too. 

By 1610, she had inspired one of the first female celebrity biographies, The Madde Prancks of Merry Moll of the Bankside, with her walks in Man’s Apparel and to what Purpose by the playwright John Day. In 1611, two of the most successful writers of the age, Thomas Dekker and Thomas Middleton, asked her to close a performance of the play they had written about her, The Roaring Girl. This was the big time – an audience of 2,000 people watched Moll Cutpurse play herself.

This stunt proved too much for the authorities.

Despite the tradition of theatrical cross-dressing, a woman dressing as a man openly on the streets of Jacobean London was breaking the law. Mary was arrested for immoral behaviour and thrown into the correction house at Bridewell where she was whipped and forced to beat hemp stalks into rope. After three months, she re-emerged and took up where she left off. 

On Christmas Eve 1611, she was re-arrested for the same offence “to the disgrace of all womanhood”. This time she was hauled up in front of the Bishop of London, charged with prostitution as well as cross-dressing. The bishop pressed her to confess that she was “sexually incontinent”, but Mary would have none of it.

The Upside DownBack to the Future

John Mitchinson

She cheerfully admitted to being a foul-mouthed, drunken thief, a gambler and a bear-baiter, but she objected to the accusation that she had sold her body. Though she looked like a man, she told the assembled clerics, a visit to her lodgings would show she was every bit a woman. This saucy response outraged the bishop. 

She was sentenced to public penance (dressed in a white shift) at the cross outside old St Paul’s. Mary turned it into a command performance, drinking herself insensible on six pints of sherry and weeping so piteously that the authorities released her to preserve the peace.

Mary had a very modern instinct for making money from fame.

By the time she was 30, she was a major player in the London underworld. Her days as a thief, and her hours spent in the bear gardens and taverns, had built up an unrivalled network of contacts on both sides of the law. This made her the perfect broker for stolen goods, but it also opened a new line of business: wealthy women looking for male companions. With the single-mindedness she brought to all her business ventures, she “chose the sprucest fellows the town afforded” and turned her house into an escort agency. 

Busy as she was with fencing and pimping, Mary would still occasionally play Moll.

The vintner and showman William Banks bet her £20 that she wouldn’t ride from Charing Cross to Shoreditch dressed as a man. Of course, she did so in style, flaunting a banner, blowing a trumpet and causing a riot in the process. Part of the excitement was because the horse she was riding was Banks’ Marocco, the most famous performing animal in London. Shod in silver, it could dance, play dice, count money and generally astonish audiences with its intelligence and dexterity. Moll Cutpurse riding Banks’ Horse would have been the Jacobean equivalent of Billie Eilish playing on stage with Paul McCartney.

It is this irrepressible side to Mary’s character that seems as fresh as ever. 

If the idea of ‘bawdy’ has fallen victim to over-the-top costume dramas, full of ale-swigging wenches in low-cut dresses, the word originally meant ‘joyous’. The joy that Mary brought to others with her unconventional life was borne out by the people who knew her. “She has the spirit of four great parishes,” wrote Middleton and Dekker, “and a voice that will drown all the city.”

Her final request was to be laid face down in her coffin because “as I have in my life been preposterous, so I may be in my death” – but it’s John Milton’s epitaph that captures her subversive spirit best: “She’ll stand alone, and none come nigh her.”

John Mitchinson is a writer and publisher and co-founder of Unbound, the world’s leading crowdfunding platform for books. He was one of the founders of BBC’s ‘QI


Byline Times is funded by its subscribers. Receive our monthly print edition and help to support fearless, independent journalism.

New to Byline Times? Find out more about us


A new type of newspaper – independent, fearless, outside the system. Fund a better media.

Don’t miss a story! Sign up to our newsletter (and get a free edition posted to you)

Our leading investigations include: empire & the culture warBrexit, crony contractsRussian interferencethe Coronavirus pandemicdemocracy in danger, and the crisis in British journalism. We also introduce new voices of colour in Our Lives Matter.

More stories filed under The Upside Down

The Upside Down: Why We Underestimate Fungi at Our Peril

, 17 March 2023
Perhaps it is the atavistic fear of something growing inside us and consuming us from within that makes us feel so ambivalent towards fungi, writes John Mitchinson

The Upside Down: Why the Tuskegee Experiment Still Resonates

, 17 February 2023
John Mitchinson explores the lasting impact of a controversial American study steeped in the institutional racism which continues to permeate the country today

The Upside Down: Why Folk Songs Still Mean Something

, 13 January 2023
The longer we look at this traditional music, the more we see that its very malleability is its strength and its challenge, writes John Mitchinson

More stories filed under Culture

‘The Strangers’ Case? The Government’s Approach to Human Dignity, Asylum Seekers and a Lesson from Shakespeare’

, 30 March 2023
We must all examine our values and actions in relation to vulnerable populations, writes Iain Overton

The Upside Down: Why We Underestimate Fungi at Our Peril

, 17 March 2023
Perhaps it is the atavistic fear of something growing inside us and consuming us from within that makes us feel so ambivalent towards fungi, writes John Mitchinson

‘Hanif Kureishi and the Touch of Forced Intimacy’

, 16 March 2023
Stefano Goodman explains how impairment can lead to sudden physical reliance on strangers – and how this shapes our personalities

More from the Byline Family