A Brief History of How Drag Queens Turned Against the Trans Community

Last week, in an interview with The Guardian that hyped the “radical message” of RuPaul’s Drag Race, the superstar drag queen was asked whether he would allow people whose gender identity was female to compete on the show. Regarding transgender women who have had breast implants or undergone hormone replacement therapy, RuPaul said they would “probably not” be eligible to compete on the show — “it changes the whole concept of what we’re doing” — and doubled down on Twitter by comparing trans drag queens to steroid-abusing professional athletes, before apologizing amid a wave of backlash.

Whereas the drag and trans communities were once closely allied, this sort of antagonism has colored trans people’s perceptions of drag for years, especially among younger trans women and transfeminine people. The day before Drag Race All Stars’ season three premiere in January, a user of the subreddit r/Asktransgender asked “Who else has a problem with drag?” to describe the hurt she felt at being lumped in with the “man in a dress” by cisgender audiences. Responses were mixed: Some laid blame with individual performers, but many seemed to think the well itself was poisoned. One user called drag “frequently somewhere between casually and blatantly misogynistic,” while several went so far as to compare it outright to blackface.

According to Ben Power, executive director of the Sexual Minorities Archive in Holyoke, Massachusetts, the last time in recent memory that drag itself was under such heavy fire was when it became a target of lesbian separatists in the 1970s. The only major difference today, he says, is that “the people doing the judging changed.”

How did this happen? At what point did drag become the source of so much controversy under the queer umbrella? And most important: What do we do, now that there’s no going back?

While starting with crossdressing in Shakespearean-era theatre might seem a little too far back, it’s vital to note drag’s early, chimeric history before we get too far in the weeds. (This overview should not be considered comprehensive; as a white trans woman, I yield analysis of drag’s relationship with race to transfeminine people of color.) At one point, “female impersonation” was one of the most commonplace ideas in Western performing arts; young boys played female roles as a matter of course, and nobody would have thought to question their sexuality or gender. Drag as specifically queer performance did not yet exist, because the necessary context had yet to arrive.

By the 1800s, that context was well on its way in America. White men often portrayed female minstrel show characters, milking “man in a dress” humor alongside the shows’ racism. Yet even as the public devoured female impersonation in entertainment, cross-gender expression was otherwise thoroughly policed. In Columbus, Ohio, laws against public crossdressing were established in 1848, spreading to other cities in the following decades — partially an attempt to stop women from enlisting in the military but also meant to shore up God-given gender roles and discourage sodomy, too.

As “dressing up” in public became more dangerous, fledgling 19th century queer communities naturally sought to circumvent the new laws. Some of the earliest, albeit suspect, information we have about explicitly queer drag dates back to 1893; in Gay American History, Jonathan Katz reprints one doctor’s letter to a medical journal warning of “an annual convocation of negro men called the drag dance, which is an orgie of lascivious debauchery.”

Over ensuing decades, lines between drag, crossdressing, and transsexual identification blurred significantly, separated only by semi-porous membranes of politics and genderfuckery. As minstrel shows gave way to the rise of vaudeville and radio, drag drifted away from the mainstream to become a staple of gay nightlife, bringing with it a new paradigm for queer identification. In How Sex Changed: A History of Transsexuality in the United States, Joanne Meyerowitz notes that the 1950s “female impersonator” community served as a safe haven for prospective trans women to sort out their gender issues.

Queens of the time did more than carefully impersonate celebrities and replicate “feminine” mannerisms: Many underwent early hormone replacement therapy to grow real breasts, and would provide “purple pills” to their less experienced charges along with “encouragement to pursue a woman’s life offstage.” One trans woman who worked as a female impersonator asserted in an interview that although most queens had once denied any desire for bottom surgery, she knew “half a dozen impersonators…[who were] saving for the operation” by the mid-1960s. Knowing others who had surgically transitioned, she believed, had mollified their fears.

Perhaps nobody was more emblematic of drag’s nebulous placement within queer identification than Sylvia Rivera. Widely considered to be one of the instigators of the Stonewall riots in 1969, Rivera is today revered as something of a saint within the transgender community — somewhat ironic, as Rivera herself rejected that term and others. “I’m tired of being labeled. I don’t even like the label transgender,” Rivera wrote in a 2002 essay. “I just want to be who I am.” Rivera’s sense of gender seemed too expansive for any one word, and she drifted through countless categories over the course of her life. But one identity the STAR co-founder never disavowed was “queen.”

These fluid dynamics of identification and belonging are evident in America’s first transgender periodicals. Drag magazine printed tips on hormone therapy, gender identity clinics and gender-affirming surgeons. Later issues gave pride of place to erotic centerfolds but still celebrated civil rights successes, like a disabled trans woman’s 1980 request for bottom surgery — “the first time a federally funded medical care program [Medicaid] has recognized transsexuality.” The reverse was true for magazines like Transgender Tapestry (originally TV/TS Tapestry), published from 1979 to 2008. Much of each issue focused on building “transvestite/transsexual” community, but drag featured prominently in its news coverage and analytical essays.

Even drag queens who didn’t necessarily identify with transsexuals or crossdressers fought for the rights of both. A 1975 Drag special supplement opened with “The Drag Times,” a short news section dedicated to transgender civil rights struggles. One story told of drag queens and allies who picketed a hotel in San Francisco’s Tenderloin district to protest housing discrimination and police mistreatment. That spirit would continue for decades; in an essay for Transgender Tapestry’s Summer 1997 issue, “What Do Drag Queens Want?,” Tim Denesha writes that “drags want...to make the world a better place,” noting the thousands raised for AIDS research yearly through the drag circuit’s grassroots Imperial Court system.

A primary reason for much of this inter-community cooperation was the consolidation of political power. Drag queens, transvestites, and transsexuals of the 1970s shared an obvious set of common goals, which include abolishing the myriad of laws that outlawed crossdressing across America. Gender-conforming gay men were no help; a 1975 Drag essay noted that “the gays in their movement for liberation seemingly feel that drags have a worse public image, and so have virtually disowned us.”

But those networks had more practical day-to-day purposes, such as keeping people alive. STAR, the organization founded by Rivera and fellow queen Marsha P. Johnson, served homeless queer youth of color, regardless of categorical identification. This would become invaluable during the AIDS epidemic in the 1980s; trans women were among those frequently cast out from their disease-fearing biological families, finding their way to drag families instead (as can be observed firsthand in Jennie Livingston’s iconic documentary Paris Is Burning).

The early 1990s saw an explosion in the East Village drag scene, stoking flames for a comeback of female impersonation in cisgender-friendly contexts. But it was a San Diego–born queen who built them into a roaring bonfire: RuPaul. After releasing his hit single “Supermodel” in 1992, drag exploded, becoming a mass-media sensation for much of the decade. “RuPaul was the cover girl of the ’90s,” as sociology scholar Suzanna Danuta Walters notes in her book All the Rage: The Story of Gay Visibility in America.

Elsewhere in pop culture, films like To Wong Foo, Thanks for Everything! Julie Newmar (1995) and The Birdcage (1996) were opening-weekend hits, and Mrs. Doubtfire (1993) became a national touchstone. “[C]ross-dressing, straight-talking drag queens emerged as our Dear Abbys — providing sassy but affectionate insight into the vicissitudes of heterosexual romance,” writes Danuta. Yet though the “curious cultural fascination” with drag performers burned hot, it did “not necessarily entail a challenge to traditional definitions of gender. [....] In films and popular culture generally, drag becomes a safe and circuitous way” of dealing with queerness, rather than a radical cross-gender experience. A major part of this was clearly the emphasis on cisgender drag queens; in the 1990s, no trans queen could hope for RuPaul’s level of fame and acceptance.

The drag boom dimmed by the mid-’90s, but it came with more than its fair share of cultural osmosis. For one thing, drag no longer had a “public image” problem — at least, not as far as gay men were concerned; a quick rewrite of drag history was all that was needed. Julian Fleishman’s 1997 book The Drag Queens of New York, compiled through interviews with RuPaul and his contemporaries, casually opines that “when a man who wishes to be a woman…succeeds in becoming one, he is no longer a drag queen” and that though real queens might “experiment” with transitioning, “they invariably stop short of the surgical point of no return.” But though the historical revisionism of gay men’s relationship with drag was damaging, another component of the ’90s drag boom had deeper effects: Cisgender Americans now had a whole new way of looking at and talking about transgender people, and many manipulated that vocabulary to twisted ends.

To continue this discussion, we first need to talk about slurs like “tranny” — a word that, in roughly a half-century of use, has developed a shield of contradictory etymologies that makes parsing its use a daunting task. Like other words considered trans slurs today, its origins remain unclear, and will likely depend on who you talk to. Trans performance artist and writer Kate Bornstein, for example, will tell you “tranny” comes from Australian drag performers and transvestites, and has been used as a term of endearment for decades. Others have been unable to trace its roots past 1983, when it apparently entered the North American gay male lexicon. Though “tranny” certainly saw casual use among sex workers and drag queens, there’s also plenty of evidence for early pushback among transsexual-identified people. Among the most vocally opposed was activist Xanthra Philippa Mackay, who distributed a button through her small-press operation Genderpress: “DON’T CALL ME TRANNIE, SHITFACE”.

Its coinage may remain a mystery, but the use of “tranny” among drag queens certainly helped propel the term into the mainstream. “Tranny” had no major presence in cisgender, heterosexual spaces before the mid-’90s, but by the late 2000s it was ubiquitous, with drag’s surge in popularity being the most relevant cultural factor. One particularly tense exchange on Caitlyn Jenner’s reality series I Am Cait illustrates how fast the change came, as well as how deep the linguistic divide over “tranny” had become: The show’s second season placed Bornstein (a product of the ’80s and ’90s) against fellow writer Jenny Boylan, who came out publicly in 2002 when her memoir She’s Not There made her the first trans woman to write a New York Times bestseller. “It’s a word I associate with beatings,” says Boylan, describing a half-hour assault that left her traumatized. “For me, it’s a triggering word.” Even so, Bornstein pushed back: “You need to hear the love and respect in my voice when I say it….I know it’s asking a lot. [But] it’s my name. It’s who I am.”

Similar conversations were already taking place in the 2000s, while RuPaul prepared songs like “Tranny Chaser” and “Ladyboy” for his album Champion — either unaware or indifferent to the violence that had become associated with either slur. Drag Race premiered along with the album in 2009, casting slurs merrily in its wake, much to the consternation of some viewers. When trans activists finally lobbied against RuPaul’s language in 2014, in particular a segment called “Female or Shemale” (in which contestants were asked to guess which of two pictures was of a “real” woman), the star was livid. In an appearance that May on comedian Marc Maron’s podcast WTF, RuPaul lashed out, claiming that “it’s not the trans community” who had a problem with his actions over the years. “These are fringe people who are looking for storylines to strengthen their identity as victims,” he fumed. “‘Words hurt me!’ Bitch, you need to get stronger.”

They were, frankly, cruel words from a man who has declined to analyze his role in popularizing slurs — yet far from the most toxic thing a Drag Race affiliate would do. In response to the backlash, Drag Race contestant Justin “Alaska Thunderfuck” Honard posted a YouTube video in which the queen theatrically shot a representation of trans activists (named “Joy Less” and wearing a moustache and wig) in the face. Alaska later apologized (to Parker Molloy, the activist who many believe inspired “Joy Less”) and removed the video, saying that he wanted to combine trans activism’s “passion and conviction” with drag’s “marketable charisma.” But war had already been declared; amid the din, trans activist Zinnia Jones would post a massive essay arguing that modern drag “hurts trans women and achieves little or nothing of value.”

Which brings us, once again, to our conundrum: What now?

How and when these tensions arose now seem, if not clear, at least less opaque. But can we truly say drag “went wrong”? Or have high-profile performers simply failed to adapt? The answer is a little of both. The primary culprits may be concentrated at the top, but the toxicity they introduce has been far-reaching.

“There are a lot of people that still perform very binary, transphobic, misogynistic, racist drag, and they don't care to do the work to change,” writes Cassidy Liebman over email, a trans man and former assistant to Drag Race contestant Sasha Velour who performs as drag king Vigor Mortis. (Disclosure: Liebman is also a personal friend.) “That kind of drag is unfortunately still tolerated widely in cis gay spaces.”

Liebman’s own path to drag was a healing one — and he knows how lucky that is. “Drag was essential to my coming-out process,” he writes. “I couldn’t run any longer once I got up on that stage…it was my first time being perceived in more of a way that I identified with.” His experience is far from universal, though. “I have seen both transmasculine and transfeminine people met with aggression, exclusion, [and] physical assault,” he says. “It needs to stop.”

Clearly, some drag performers’ attitudes and actions towards trans people need an overhaul. One way to accomplish that may be a revival of the tactics of late-20th-century activist queens — those who would gather a dozen other queens and allies to picket a hotel or, like Rivera and Johnson, organize collectives to benefit homeless queer youth. In Drag: A History of Female Impersonation in the Performing Arts, Roger Baker observes that “[d]rag has always been a powerful weapon. But it is rarely loaded and pointed in the right direction.” Baker intended those words to lionize RuPaul; today, they read as an indictment. For reconciliation to occur, drag stars must stop punching down on the trans community, especially at such a fragile stage in its struggle for civil rights. And while trans activist queens like Carmen Carrera and Courtney Act do good work, they’re few and far between, and they don’t often get involved with radical community activism.

That’s all easier said than done, though, and it’s unclear who might step up to fill those roles — especially since there’s little pressure to do so. Four years after his conversation with Molloy, Honard — or at least his Alaska persona — is still largely invisible in activism (the odd #BlackLivesMatter retweet notwithstanding). As Honard told Bust in a recent interview, he’s “not afraid of losing fans or followers for saying the president is a reckless asshole.” But does that fearlessness extend to issues facing the trans community, like police violence, income inequality, or immigration reform? Not according to his Twitter — and that silence, compounded by that of Honard’s fellow stars like Bianca Del Rio, speaks volumes about how mainstream queens choose to use their platforms

Of course, the same doesn’t necessarily hold true for smaller-scale drag performers, who are often very engaged in their communities. When they are, it can serve as a wake-up call that drag still possesses transgressive value in cishet spaces. Drag Queen Story Time (where queens visit libraries to read to local children) is a regular event in cities like New York and San Francisco, but when the Broome County Public Library in central New York State announced its first such event in January, it was met with outrage. Patrons accused the library of “normalizing perversion,” “indoctrinating children,” and making the county’s youth “pawns in a dangerous game.”

Seeing that sort of backlash, it’s easy to understand another reason trans people don’t always want to be associated with drag — after all, this line of thinking usually ends with accusations that the “transgender movement targets kids” for grooming, and not everyone restricts their anger to the Internet. But for young and questioning LGBTQ+ folk, especially those in more rural areas, drag still posits a radical idea: Queering gender performance isn’t just acceptable and normal, it’s fun.

As Zinnia Jones noted in her 2014 essay, it would be ludicrous to expect trans people to accept drag back under the “transgender” umbrella, where it once rested semi-comfortably; still, its current position as a mostly acceptable entryway for people to try on new modes of being themselves remains valuable. Jones asserts that drag is “unchallenging and nonconfrontational,” but that’s only true up to a point — beyond which lies a world where drag could make a massive impact on millions of people’s lives, if only its famous practitioners wielded it with a greater sense of consciousness and responsibility.

Frustratingly, the best course may simply be to wait for drag to reinvent itself all over again. Liebman remains hopeful, seeing the growing popularity of “alt-drag” and “queer drag” — ”a world where all are welcome, and toxic bullshit will not be tolerated,” and where assimilation gives way to liberation. “I have had the pleasure to work with and know so many glorious performers from every inch of the gender spectrum, performing drag as traditional as embodying an intricately detailed celebrity impression to slapping on some Chap Stick and a jockstrap,” he says. “And they all left the stage on fire and the crowds screaming.”

Now that’s a performance both trans people and cis gay men can hopefully get behind.

Samantha Riedel is a writer and editor whose work on transgender culture and politics has previously appeared in VICE, Bitch Magazine, and The Establishment. She lives in Massachusetts, where she is presently at work on her first manuscript.