A case for transgender players.
“Aliases, gender dysphoria, cross-dressing, bisexuality, homosexuality and performing have always gone hand in hand.”
OUTING lesbian, gay, bisexual, transgender and intersex (LGBTI) performers has long been an emotive and legal tightrope for historians, but 400 years since William Shakespeare’s death, it’s time to look where academics have feared to glance.
When Shakespeare’s fellow actors John Heminges and Henry Condell oversaw the publication of his complete works in 1623, they included a page of “The names of the Principall Actors in all these Playes”.
It was never illegal for women to perform on the stage in Shakespeare’s era, but it was seen as an unthinkable moral breach akin to prostitution. The solution was to cast boys in the female roles.
So of this list of twenty-six male performers, which must include those who played heroines from Juliet to Cleopatra, which fellows donned the skirts?

Ruling out those credited with male roles leaves a cluster of men who began their careers as ‘boy players’ and wouldn’t register on any acting roll of honour – Alexander Cooke, John Shancke, Samuel Crosse, Nathan Field and Nicholas Tooley – yet all were shareholders in England’s premier theatre company The King’s Men.
Henry VIII’s Buggery Act of 1533 ensured LGBTIs remained invisible for centuries in the performing arts, however, it’s simply not credible to assume all the men on Shakespeare’s cast list were straight.
So I’ll add historical evidence to conjecture and show how easy it is to make room for a same sex-attracted transgender woman within a Shakespearean playhouse, and why she left almost no trace.
The record shows that twice-widowed Susan Tooley was on the market for husband number three in 1592. If we imagine her 10-year-old son, Nicholas, showed early signs of acting skill, we can paint Susan as a stage mother who made use of a known link the boy’s father’s family had to the Stratford-upon-Avon Shakespeares.
“Shakespeare attempted to dampen the Puritan inferno by writing a batch of heroines who cross-dressed as men.”
If the Tooleys – landed Warwickshire gentry – agreed to make the introductions that got the child off Susan’s genteel apron strings and into the hotbed of sodomy and vice that the Elizabethan playhouse was considered to be, I imagine they enforced one important condition. The boy, by that time listed in the records of London’s Court of Orphans as ‘orphan Tooley’, would have needed an assumed name.
We know from his will that Nicholas Tooley had an alias – the undistinguished surname ‘Wilkinson’. Perhaps it was coined for him in 1595, when a gifted lad was required for a crucial role in a new play?
Pamphlets from that decade reveal the playhouses came under the most intense Puritanical fire against boys cross-dressing on the public stage. If it was ‘orphan Tooley’ who appeared opposite Richard Burbage in the world premiere of Romeo and Juliet, the 13-year-old may wisely have cross-dressed as ‘Nick Wilkinson’.
Imagining the production was a hit allows us to cast ‘player Wilkinson’ opposite Burbage in Shakespeare’s regular new plays. The workload, and the pressure to maintain a slight physique, may have led the teenager, twice in 1599, to seek treatment from Simon Forman, London’s leading astrologer and herbalist. Forman’s notes reveal Tooley complained to him of “melancholy… moch gnawing in his stomak & stuffing in his Lungs.”
We know Shakespeare attempted to dampen the Puritan inferno by writing a batch of heroines who cross-dressed as men; but this could also have been a way to make performing lead female roles easier on one talented, ailing adolescent. The playwright let audiences in on the laughs, however, and created some of the best homoerotic scenes in theatre history, in Twelfth Night and As You Like It.

When ‘orphan Tooley’ reached his majority in 1603, Richard Burbage applied to the Court of Orphans to have him indentured. Clearly, ‘player Wilkinson’ had become indispensable, and since the authority had no choice but to use his birth name on the paperwork, Nicholas Tooley finally emerged as a player.
Under the terms of his apprenticeship, the young man was accommodated by the wider Burbage family, London’s leading theatrical dynasty.
Surely it was the relentless playhouse work, wrangling not only his own scripts but also his master’s, performing before enormous crowds in the pre-eminent popular entertainments of the day, that led to Tooley’s elevation to shareholder of The King’s Men by 1605.
For anyone on the payroll to make a career as a leading lady would have drawn plenty of negative attention; but Shakespeare’s next move suggests he recognised the dramatic potential of one man’s ability to convincingly inhabit feminine authority, passion and lust.
When the playwright dropped the cross-dressing of comic female heroines and created his most complex female roles – Desdemona (1603), Lady Macbeth and Cleopatra (both 1606) – one review showed the impact.
In a performance of Othello by the King’s Men in 1610, a consummate actress fooled diarist Henry Jackson into writing: “She always acted the matter very well, in her death moved us still more greatly; when lying in bed she implored the pity of those watching with her countenance alone.”
Was this Desdemona played by Nicholas Tooley at the height of ‘her’ powers?

Onstage gender boundaries were being tested. In 1611, Londoners were thrilled and scandalised by the performance of a woman at the Fortune Theatre – Mary Frith, alias Moll Cutpurse, the infamous ‘Roaring Girl’.
Her subsequent confession to the Consistory Court states: “She told the company there p[re]sent that she thought many of them were of the opinion that she was a man, but if any of them would come to her lodging they should finde that she is a woman & some other immodest & lascivious speaches she also vsed at that time And also sat there vppon the stage in the publique viewe of all the people there p[rese]nte in mans apparrell & playd vppon her lute & sange a songe.”
Mary’s arrest, public shaming and penance were the playhouse gossip of the 1612 season and surely struck fear in the heart of every cross-dressing performer.
Now 30, Tooley was overlooked for the title role in a play by the newest writer on the scene, John Webster, whose The Duchess of Malfi ushered in the next generation of boy players, playwrights and shareholders.
My story, Merely Players, drew inspiration from this pivotal moment in Western theatre history.
Tooley’s one documented attempt at playing a male role was in Webster’s hit tragedy, while witnessing his replacement emerge; so it’s not a stretch to imagine his melancholy returned with force as he struggled to maintain his identity in the playhouse.
It’s also common for an intense period of playing passionate lovers to lay fertile ground for a relationship offstage; so it’s not incredible to suggest that Tooley and Burbage had an ongoing affair that came under threat as master’s career continued while apprentice’s declined.
My story has Tooley making a gender transition while disappearing for years into one of the few places that I believe would have taken him in – London’s Convent of Saint Helen. Here, she may have fooled the nuns into thinking she was a woman. The name I imagine was easiest for her to adopt was one she’d already used – Mistress Wilkinson.
After hearing that her old master is not well, I have her strolling back into the Globe playhouse in 1619, where she uncovers much hanging in the balance.
“Any number of participants in Western theatre’s groundbreaking era could have been LGBTIs.”
Before his death in 1623, the never-married Nicholas Tooley used his birth name to legitimise significant financial gifts to a coterie of women, including his master’s sister-in-law Elizabeth Burbage, “in whose howse I doe now lodge as a remembrance of my love in respect of her motherlie care over mee”. He stipulated the funds were to be paid into the womens’ “owne proper hands” and not to any husband.
The document reveals a man who spent much time in the company of a large number of women, and knew the legal impediment that marriage placed on daughters, wives and sisters inheriting monies independently.
But Tooley also signed a codicil identifying himself as “Nicholas Wilkinson alias Nicholas Tooley”, which no historian has ever thought to investigate as a cisgender dead name.
Any number of participants in Western theatre’s groundbreaking era could have been LGBTIQ, it’s simply a matter of ending the academic silence.
Aliases, gender dysphoria, cross-dressing, bisexuality, homosexuality and performing have always gone hand in hand, and apart from sharing the stage when cisgender English women finally got public support for bursting onto the stage in the 1660s, in 400 years not much has changed behind the scenes.
This article was first published on Gay Star News and appears in Michael’s book ‘Merely Players: Acting like Shakespeare really matters’.
© Michael Burge, all rights reserved.