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Drag kings, the gender rebels that history forgot: The fascinating legacy of male impersonators

Thanks to the meteoric rise of RuPaul’s Drag Race, drag is now thoroughly mainstream. But while drag queens have extended their six-inch heels into the spotlight, drag kings, performance artists who critique masculinity, have been left on the margins of pop culture. Christobel Hastings explores a forgotten era when women were crossing gender lines, experimenting with their identity, and becoming international stars on their own terms

The year was 1912, and on a warm summer’s night, the first ever Royal Command Performance of Variety took place at the Palace Theatre in London’s West End. The bill was a rich and eclectic mix of entertainers; singers, dancers, comedians and magicians, each one hoping to impress the crowd, and more importantly, win the approval of George V and Queen Mary. By all accounts, the Royal party enjoyed the spectacle, except for one moment when a male impersonator by the name of Vesta Tilley took to the stage to perform a lively rendition of Algy, The Piccadilly Johnny. Scandalised by the sight of a woman wearing trousers, the Queen reportedly buried her face in her theatre programme.

Tilley’s performance was no wildcard. She was, in fact, the highest-paid female entertainer on the British stage, commanding sums of £1,000 a week for impersonating men from all walks of life. Over a century later, and while drag kings, a movement of performers who don masculine drag and critique male gender stereotypes have grown in visibility, they nevertheless remain on the margins of mainstream pop culture. But while the scene may still be in its infancy, there have always been women who have pushed the boundaries of gender. 

150 years ago, in fact, a rich seam of female performers were skewering masculinity on stage in a subculture that’s all but been forgotten. To trace the legacy of drag kings, we have to travel back to the mid-19th century, when the first generation of male impersonators were treading the boards of British music hall, and becoming international stars.

The birth of British music hall

Loud, lively and filled with a merry-go-round of speciality acts, Victorian music halls took off during the 1850s as a form of entertainment for the working classes. Given the trend for gossiping about the news and scandals of the era, (as well as a taste for alchohol) the halls were the perfect place to experiment with gender expression. During the 1860s, as demand for performers increased, working class women found unprecedented freedom in the halls, many of them taking their cues from lions comiques, male performers who parodied middle and upper-class male behaviour. 

Among them was Annie Hindle, a performer who could transform into men from all walks of life, as well as win favour with her takes on everything from courtship and marriage to class solidarity. With short clipped hair, a low alto voice and realistic costume, Hindle thrilled the scene with her manly gestures, comic improvisation and quick-fire changes in the wings. “To the men in her audience who thought of women as the naturally weaker sex and as being fundamentally different from men,” Gillian Rodgers notes in Just One of the Boys, “Hindle’s act elicited wonder and amazement.”

So successful was Hindle that in August 1868, she journeyed to the US to take on the variety stage – not before hyping herself as “Miss Annie Hindle, serio-comic and the greatest male impersonator in the world” in a number of newspaper adverts before her arrival. It was here that the expat really found her footing as the first male impersonator in American variety, and before long was booked seasons in advance. 

However, Hindle’s act soon inspired competition. By the mid-1870s, when the term ‘male impersonator’ first came into use, other stars such as Ella Wesner, another British music hall expat, were exciting the New York theatre scene with their masculine performances. Wesner too was from the school of theatrical realism, deftly switching between characters, from flashy, upper-class “swells” and dandies, to working-class men with whom she found favour by empathising with their struggles. So convincing was her style, that a review in the New York Clipper following her debut declared, “She might easily walk Broadway in male attire without her sex being suspected.” Wesner was so devoted to her craft, that she actually even left instructions that she be buried in male attire when she died.

Given the strict social mores of the era, it’s no mean feat that Hindle and Wesner managed to establish male impersonation as an art form, not least win the admiration of both men and women in their audiences. In fact, as it’s noted in Queer Episodes in Music and Modern Identity, newspaper reviewers “gave no indication that any portion of their acts or their appearance as any type of character was seen as transgressing standards of decency,” and even treated them in the same way as the male performers that they performed with. And though their appeal, as Gillian Rodgers asserts, “lay in the commentary they provided on manhood in this period, and their ability to both celebrate and denigrate different constructions of masculinity,” it seems no less remarkable that women whose livelihood lay in teasing the very currency of power and privilege, were sitting at the heart of showbusiness.  

A new generation in the wings

Come the turn of the century, one woman was dominating male impersonation both in American vaudeville and British music halls. Matilda Powles, known by her stage name, Vesta Tilley, was a British expat who cut her teeth on the music hall circuit. Unlike her contemporaries, who were in the business of theatrical realism, Tilley sought to reinvent the genre on her own terms. While her hair was short and clothes were distinctly masculine, they still revealed the curves of her form; although she gave courtship advice, she sang in a higher register, keeping strictly to her script instead of riffing with the audience.

If her forebears had prided themselves on appearing as macho as possible, Tilley’s impersonation style always put her femininity firmly in the spotlight. Although some critics have pointed out that her androgynous gender presentation demonstrated a shrewd awareness of staying within the confines of heteronormativity, there’s no doubt her performances were still subversive. Hits such as Jolly Good Luck to the Girl Who Loves a Soldier mocked promiscuous soldiers, while Burlington Bertie poked fun at a pretentious aristocrat. 

Tilley wasn’t the only woman reinventing male impersonation in the early 1900s. Her rival, Hetty King, was also a popular music hall entertainer, whose repertoire featured an impressive range of nautical characters. During the World Wars, she usually performed as either a soldier or sailor, scoring hits with songs such as Ship Ahoy (All The Nice Girls Love A Sailor). Then there was Ella Shields, an American export to British music hall who swung away from Tilley’s impersonation style and brought back the theatrical realism initially pioneered by the likes of Hindle and Wesner. In 1915, she hit the bigtime with her comic rendition of  Burlington Bertie from Bow (originally popularised by Tilley) and toured to critical acclaim during the 1920s.

It’s worth noting that although Hindle and Wesner had relationships with women, queerness wasn’t inherently tied to male impersonation during this period. Many female performance artists, like Tilley, King and Shields, were actually married women, who carefully managed the gender expectations of the time by avoiding first-person references to women in their songs, rejecting male attire in their daily lives, even condemning gender non-conforming behaviour and homosexuality. That’s not to say that there weren’t performers who used their impersonation as a means to embrace their queer identity and expand the definitions of gender and sexuality, as Gladys Alberta Bentley, a gender-bending blues performer of the Harlem Renaissance, proved.

Just a teenager when she arrived in Harlem around 1925, Bentley was a woman who broke ground in virtually every way possible. After establishing herself as a regular performer at rent parties (private parties intended to raise rent money by charging admission) and getting her big break at the Mad House as a pianist, Bentley electrified the New York club scene with her provocative, blues-infused male impersonation. She graduated onto famous gay speakeasies like The Clam House and Connie’s Inn, where she pounded out risqué parodies of popular songs on the piano, improvised with trumpet-like scat, and improvised suggestive lyrics in her powerful alto that ran the spectrum from mildly suggestive to downright lewd. Her performances brought both celebrity and notoriety, and for a while, she was considered one of the most famous entertainers in the United States.

Bentley didn’t just stoke controversy with her risqué songs; she challenged social norms with her gender expression, too. The performer cut a mighty figure in male attire, donning a top hat, bow-tie and her trademark white tuxedo when she took to the stage, and according to writer Wilbur Young, Bentey could be seen “marching down Seventh Avenue attired in men’s clothes any day of the week”.

It was her wholly unique presentation that James F. Wilson argues allowed her to “tease the boundaries between male and female, homosexual and heterosexual, aristocrat and working class, and white and black.” Despite the greater freedoms for LGBTQ+ people in Prohibition-era Harlem, there’s no doubt Bentley’s unapologetic lesbianism was remarkably bold. She made no attempt to hide her same-sex attraction when she flirted with women in the audiences, and scandalised early 20th century society when she told a gossip columnist for the New York Evening Graphic that she had a same-sex civil ceremony in New York with a white woman.

The final curtain call

By the 1930s, the golden era of male impersonation was over. In America, a new conservatism took hold as the Great Depression loomed large. In Britain, music halls gradually disappeared too, with only two seasoned performers, Hetty King and Ella Shields, representing the art form into the 1950s. One of last standout performers was Stormé Delaverie, who performed with the Jewel Box Revue for fourteen years, from January 1955 until September 1969. A drag performer and staunch gay rights activist, Delaverie resisted all attempts to categorise her race, gender identity and sexuality orientation. It’s rumoured that she even threw the first punch at the Stonewall Inn in Greenwich Village that ignited the 1969 riots.

It is upon the legacy of male impersonation that drag kings rose to prominence in the 90s, and have been growing their community ever since. This new generation of performance artists have been able to fully critique the trappings of masculinity, expanding the genre with a spectrum of gender expressions previously unseen in drag king culture. 

Despite progress, there is still a lack of mainstream awareness about the roots of the movement, while modern drag kings are still fighting to get the attention they deserve. The path to getting drag kings their rightful place in the spotlight is far from simple, as greater visibility comes from space, inclusion and community, both from within the drag scene, LGBTQ+ culture and mainstream society. It is a process that will take many more years to achieve anything like the recognition enjoyed by drag queens today.

It seems hard to believe that once upon a time, a woman trying on trousers could be so provocative. But without the contribution of male impersonators who dared to push the boundaries of propriety, the world of drag might not be enjoying the mainstream love it attracts in pop culture today. 

By carving out a space for self-expression, they broke down barriers of gender and class, both for the men in the audience that they impersonated, and the women who society expected to be subordinate, achieving both stardom and social change every time they took to the floor. These acts of rebellion ultimately laid the groundwork for drag kings to explore and expand gender in whichever way they see fit today. 

Images: Getty/Instagram