The First Queen of Drag

Welcome to Civics and Coffee. My name is Alycia and I am a self-professed history nerd. Each week, I am going to chat about a topic on U.S history and give you both the highlights and occasionally break down some of the complexities in history; and share stories you may not remember learning in high school. All in the time it takes to enjoy a cup of coffee. 

INTRO MUSIC

Hey everyone, welcome back. 

Did you know that the first known drag queen was a formerly enslaved black man? As we prepare to wrap up Pride month, I thought it would be fitting to look into the life of the earliest recorded drag queens in American history, William Dorsey Swann. 

A man born into slavery in Maryland just a few years before the outbreak of the Civil War, Swann carved out a new and at the time, scandalous way to express himself. His life and experience offers a compelling introduction into the long history of LGBTQ activism. However, as a Black man who was formerly enslaved and who a quote unquote unconventional lifestyle, many of the details of Swann’s life are unknown. Therefore this episode may be shorter than my standard fare. 

So who was William Dorsey Swann? How do we know of him? And what legacy did he leave for future LGBTQ activists? 

Grab your cup of coffee, peeps. Let’s do this. 

Before I begin, I want to be transparent in that there is very little scholarship about William Dorsey Swann. In fact, there appears to be a single scholar who is focused on sharing Swann’s story with the world, Channing Gerard Joseph. He is currently working on a book about Swann’s life which is due out in 2026 from what I could find on the interwebs. A majority of what I found about Swann is thanks to Joseph’s work. In fact, Joseph is credited as the scholar who first learned about Swann and brought him into the public discourse. While I normally try to vary my sources whenever I develop an episode, I decided to break the mold a little here, but to share where I got my information ahead of time. And with that, let’s begin. 

William Dorsey Swann was born into slavery in Maryland in either 1858 or 1860. He is believed to be the fifth of thirteen children from his enslaved mother Mary Jane Younker and Andrew Jackson “Jack” Swann. Given the circumstances of his birth, there is a chance that William’s father was the white land owner, but there is no evidence confirming William’s one way or the other. Regardless of who his father was, the Swann family was freed after the Civil War and bought a tract of land to support themselves. 

Swann worked in his youth, but many of the details remain obscured by the fact that there does not appear to be any journals or diaries left by Swann. He entered into the public consciousness through his arrests as a young adult for the act of quote unquote keeping a disorderly house, code for running a brothel, in the late 1880s. 

Scholars of LGBTQ history estimate that in the United States the earliest drag parties likely took place just after the Civil War in the 1860s in Harlem, New York. In its most basic form, drag is the act of wearing clothes normally attributed to the opposite sex. And using this broad definition, the act of drag - even performing in drag - was not entirely new. As early as 17th Century England, men frequently dressed up as women to perform in plays written by the famed poet and playwright, William Shakespeare. Of course, this was more a result of women being barred from performing in the theater than actual choice, but the concept of men dressing in otherwise identified female attire was not a new phenomenon. Even in the United States, dressing as the other sex was not new. Plenty of women dressed as men to serve in the Civil War, and many who went into service presenting as a man choose to continue living their lives after war in the same way.  What Swann represents, however, is someone who was choosing drag for the joy it brought to himself and others and in bringing together a community that had thus far lived largely in isolation. 

Per Joseph’s research, Swann began hosting his parties, known as drags, in 1882 in Washington, DC just a short distance from the White House. Joseph theorizes that the term drags may have been derived from the phrase grand rag, which was another phrase for a masquerade ball. Even the term drag remains debated amongst scholars, who have varied definitions of what it means and who it applies to. Some take a broad lens, using it to describe anyone who chooses to dress in clothes designated for the opposite sex, while others - like Channing Joseph - use a more focused definition where drag includes performance and competition. 

Swann’s version of drags qualifies, according to Joseph, as some of the country’s first drag shows because there was a performance element - party participants would engage in a quote unquote resistance dance also known as the cakewalk and Swann would decide on a winner, or queen, of the competition. Joseph thinks that Swann’s use of queen may have been inspired by the queens of freedom crowned during emancipation events. And while we are on the subject of queens, Swann is the first documented person to refer to themself as a queen of drag. 

In April 1888, Swann and several other men were arrested for participating in a drag party. As the police entered the party, several of the attendees flocked in the opposite direction - hoping to avoid capture and arrest. Swann, on the other hand, took a different approach. Hoping to protect the identities of his guests, Swann headed toward the members of law enforcement, trying to bar them from coming into the room and arresting his guests. He was so committed in his mission that he even got into a physical altercation, leading to the destruction of the cream colored gown he was wearing. 

Hoping to publicly shame the individuals who were in attendance, local newspapers detailed the events and published their names in the paper, writing quote: “they nearly all had on low neck and short sleeve silk dresses, several of them with trains. They all wore corsets, bustles, long hose and slippers, and everything that goes to make a female’s dress complete,” end quote. The punishment for daring to wear clothing deemed as only suitable for the opposite sex? Three months on the quote unquote farm. 

Swann would be arrested multiple times for his actions, including in 1895 where he was convicted for supposedly running a brothel and sentenced to 300 days in jail. Angered over his sentence and what must have felt like constant police harassment, Swann submitted a petition requesting a pardon to President Grover Cleveland in 1896. In arguing against the request, U.S. Attorney A.A. Birney wrote quote: “the prisoner was in fact convicted of the most horrible and disgusting offenses known to law,” end quote. Considering murder was very much a punishable crime in the 1890s, it seems quite strange that drag would be described as the most horrible, but I digress. It may come of little surprise to you, dear listener, but Swann’s request for a pardon was denied. But as Channing Joseph points out in his analysis of Swann, the simple act of demanding the pardon was revolutionary.  

Swann refused to accept that his acts were illegal or should otherwise be punished. From Joseph, quote: “Swann was the first person to dub himself a queen of drag, the first to create an organization for queer liberation, and the first to fight for their rightful place in the country they and their ancestors helped to build,” end quote. Although the decision to dress in drag was looked upon poorly, Swann remained dedicated to fostering a community where people could be their authentic selves and enjoy the company of other like-minded individuals. In this vein, Swann and his parties signify the earliest known attempt at creating a camaraderie in an era that forced many of these individuals into isolation. While Swann tried to keep his parties secret, the simple fact that he took the risk to invite others - and that others came - demonstrates that there was a growing desire to belong and people taking concrete steps to build that for themselves regardless of how abnormal their behaviors appeared to the outside world. 

William Dorsey Swann eventually moved out of the district, likely exhausted from his all too frequent contact with local law enforcement, and passed away in December of 1925. His actions may have inspired his brother Daniel, who made a career for himself in costuming the Washington drag community. But it appears as though his brother was the only last legacy of Swann’s impact. That is until Channing Gerard Joseph rediscovered Swann and his drag parties and brought his story into the light. 

Drag as a practice continued throughout the late nineteenth and into the twentieth century. It became part of vaudeville acts during the Harlem renaissance and infiltrated Hollywood, with the famed comedian Milton Berle dressing in drag as early as the 1950s. One of my favorite classic hollywood films features two very dashing men dressed as women - 1959’s Some Like It Hot which included the stunning Marilyn Monroe, but also Jack Lemon and Tony Curtis. Today, drag has hit mainstream, with plenty of opportunities for the public to watch and participate in various performances held throughout the country. 

While the resistance and protest at Stonewall is often touted as the jumping off point for the modern LGBTQ rights movement, Joseph argues it all started with William Dorsey Swann. In his analysis, Swann’s actions - his willingness to fight law enforcement, demand a presidential pardon, and host parties despite the very tangible threat - signifies the first stage of the LGBTQ rights movement. 

A man who was born into enslavement, William Dorsey Swann refused to live his life on anyone else’s terms once free. He created a space for others to build a community and pushed for what he believed was right, despite what the consequences were. He fought for himself and others - regardless of the personal cost. 

And before I sign off today, I want to give a huge thank you to Jeff and Emma who recently donated to the show through Buy Me a Coffee. I am so appreciative of the support I receive from all of you out there and it makes my day to know that you enjoy the episodes each week. Also, I mentioned a couple of weeks back that I recently started a newsletter for the podcast through substack. 

The current plan to send out a monthly newsletter detailing a historical event or person, share what I’ve been reading, and give you a glimpse behind the mic on what is happening in the Civics and Coffee universe. You can subscribe to the newsletter by visiting civics and coffee dot substack dot com or through my website at www dot civics and coffee dot com. The website is also where you can see things like source material, transcripts, and see how you can support the show like Emma and Jeff. 

I hope everyone had a happy and safe pride month. 

Thanks peeps, I’ll see you next week.

Thanks for tuning and I hope you enjoyed this episode of Civics & Coffee. If you want to hear more small snippets from american history, be sure to subscribe wherever you get your podcasts. Thanks for listening and I look forward to our next cup of coffee together. 

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