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.