The Drag King of Harlem: Gladys Bentley

The Drag King of Harlem: Gladys Bentley

Andrea Mariana

Welcome to my latest queer history blog post! If you enjoy this post, then you’ll love my Historical Fiction novels. Find out more about my projects here, and sign up for my newsletter here to stay in touch!

Note: this post contains discussion of homophobia and transphobia. Please also note that while there is some debate over which specific gender identity best describes Gladys Bentley, based on the available evidence (particularly Gladys’ self-identification) I will refer to her with she/her pronouns.

As I have observed in previous posts, the correlation of queerness to artistic genius is so robust as to be nearly cliché. But the prevalence of influential historical queer figures in the artistic world should perhaps not surprise us: the artistic disciplines, particularly the performing arts, have often abetted public and authentic expressions of queerness in all their forms. Little wonder, then, that Gladys Bentley – a deeply complex American queer icon – hails from one of the most transformative periods in cultural history: the Harlem Renaissance.

While the Harlem Renaissance was, according to Henry Louis Gates, “surely as gay as it was Black,” Gladys Bentley’s complicated narrative stands out in the lengthy list of queer Black leading lights in this remarkable period.[1] Her story, from pianist to drag king to supposedly reformed housewife, defies simplistic categorization. Her experiences, likewise, provide a window into the resistance that queer Black celebrities faced a hundred years ago – dangers which, unfortunately, persist today.

An American Renaissance

Gladys Bentley’s meteoric rise can only be understood within the context of the wider “Harlem Renaissance”, which reached its height in the post-World War I United States and ended in the 1930s. Described as “one of the most significant eras of cultural expression in the nation’s history,” the Harlem Renaissance was centered in the eponymous neighborhood of New York City but visible in urban centers throughout the country.[2]

In the early 20th century, the “Great Migration” had seen thousands of Black families flee the terrorism and rampant racial injustices imposed throughout the Jim Crow-era American South.[3] They usually settled in the major industrial hubs of the North, particularly New York City, ultimately reshaping these locales and setting the stage for a socio-cultural revolution.

Harlem, New York became the center of a Black cultural revolution in the 1920s (Image Credit: National Archives—Hulton Archive/Getty Images)

Per one analysis, “[t]he Great Migration drew to Harlem some of the greatest minds and brightest talents of the day, an astonishing array of African American artists and scholars.”[4] The list of influential Black poets, writers, musicians, singers, dancers and actors to emerge from this electric period is expansive, and left indelible marks on American arts and literature for generations to follow. But the Harlem Renaissance represented not only a flowering of Black art, but also the rapid growth of Black economic and political influence:

The neighborhood bustled with African American-owned and run publishing houses and newspapers, music companies, playhouses, nightclubs, and cabarets. The literature, music, and fashion they created defined culture and ‘cool’ for blacks and white alike, in America and around the world.”[5]

Clubs and speakeasies provided opportunities for Black performers to become the stars of an unprecedented cultural moment (Image Credit: National Archives—Hulton Archive/Getty Images)

Queer Black voices, and the queer culture(s) of the 20th century, were unmistakable in the makeup of the Harlem Renaissance. Steven Lewis, a curator at the National Museum of African American History and Culture, notes that “Black queer artists and intellectuals were among the most influential contributors to this cultural movement…From a modern vantage point, the work of these artists and their peers is part of the foundation of modern Black LGBTQ art.”[6]

However, queer Black icons – from Langston Hughes to Josephine Baker to Gladys Bentley – faced both the intensely racist socioeconomic structures endemic to this time period and queerphobic repression. The latter was especially virulent as the brilliance of the Harlem Renaissance was dimmed by the Great Depression, and the relative sexual openness of the 1920s gave way to a new phase of backlash against America’s burgeoning queer communities and public expression of queerness.

Gladys Bentley’s complex story reveals the extent to which she experienced both of these extremes over the course of her controversial career.

From Philly to Harlem

Gladys Bentley, who would ultimately become one of the stars of the Harlem Renaissance, was born in 1907 to a Trinidadian mother and an American father. She was born in Port of Spain, the Trinidadian capital, but spent her childhood in Philadelphia, Pennsylvania.[7] Sources suggest that her childhood and early teenage years were defined by tensions within her family over obvious signals of her queer orientation – particularly her romantic interests in other women.[8]

An emerging musical talent even as a young adult, Bentley absconded Philadelphia for New York City at the tender age of sixteen.[9] Bentley became a professional stage performer well before her twentieth birthday as Harlem, then Manhattan, proved fertile ground for her inventive and scandalous brand of entertainment. Bentley kicked off her career in “buffet flats” which were usually illicit clubs serving up alcohol (despite Prohibition), sex workers and fabulous performances.[10] But it was at Harry Hansberry’s Clam House on 133rd Street, a popular queer club, that Bentley’s rise to fame commenced in earnest.[11]

Bentley’s prodigious musical gifts, particularly as a pianist, secured her place as one of the stars of the Harlem Renaissance era

At these and other prominent venues, Bentley became a major attraction with her exceptional piano playing, her powerful voice and titillating Blues lyrics – some an amalgamation of popular songs of the day, others entirely of her own invention. She sang unapologetically about graphic sexual acts and the allure of women, even flirting openly with the women who attended her shows.[12] But queerness was not peripheral to her performances – rather, Bentley’s queer sexuality and perhaps gender expression were the centerpiece and selling point. She wrote of her early career:

For the customers of the club, one of the unique things about my act was the way I dressed…I wore immaculate full white dress shirts with stiff collars, small bow ties and shirts, oxfords, short Eton jackets and hair cut straight back.”[13]

Gladys Bentley brought overt queer sexuality to her powerful, enigmatic performances (Image Credit: Collection of the Smithsonian National Museum of African American History and Culture)

Her venues’ managers recognized both her talent and her magnetic charisma as a “male impersonator” (as Bentley’s performances were advertised to an eager public). By all accounts, Bentley adored women; she even claimed to have married her girlfriend (reportedly a white woman who remains unidentified) in a civil ceremony in 1931.[14] But she eschewed femininity for herself and proudly embraced her role as one of Harlem’s “drag kings”. During her later performances at the Harlem Ubangi Club, for example, Bentley’s performances featured a chorus line of drag queens in a deliberate celebration of gender reversals and flouting of cisnormativity.[15]

An advertisement featuring Bentley at the Ubangi, one of her premiere performance locations at the height of her New York fame

Throughout her prolific career as a live performer, Bentley was unabashedly daring. Her contemporary Langston Hughes, who was himself likely queer, was among her scores of admirers. He said of Bentley:

“[A]n amazing exhibition of musical energy—a large, dark, masculine lady, whose feet pounded the floor while her fingers pounded the keyboard—a perfect piece of African sculpture, animated by her own rhythm.”[16]

Fame and Fleeting Fortune

Bentley’s star continued to rise throughout the late 1920s and early 1930s even as the Great Depression deepened and the US entered prolonged economic stagnation. In addition to headlining the Ubangi Club, Bentley became a recorded artist with tracks of her most famous songs, including “How much can I stand?” and “Red beans and rice.”[17] She also appeared regularly at the Apollo Theatre and other high-profile venues in New York, and briefly held a residency in Midtown.[18] All of these engagements, and her growing celebrity, brought Bentley considerable wealth. During her most lucrative years she reportedly employed her own personal staff in a luxury apartment, enjoying the fruits of her exceptional talent.[19]

Gladys Bentley in her iconic drag performance outfits (Image credit: Collection of the Smithsonian National Museum of African American History and Culture)

But the times, however, were quickly changing. By the mid-1930s, Bentley’s fearlessly queer performances were becoming a source of tension and, even within New York City itself, the subject of backlash. The end of Prohibition coincided with the fading of the Harlem Renaissance. Beyond New York, worsening economic hardship and the drumbeat of an impending global war made the artistic vibrance of the 1920s seem increasingly out of place. But Bentley, by then a nationally known performer, took the changing zeitgeist of New York City as an opportunity to change her scenery.

In 1937, Bentley relocated to the Golden State. She was immediately successful in Los Angeles, the city which she would make her permanent home, and later in the San Francisco Bay area (already a center for the American queer community as much as New York). In the early 1940s, Gladys Bentley headlined at the lesbian establishment Mona Club 440 in San Francisco (today Club Chi-Chi). Advertisements from these years regaled her as “America’s Greatest Sepia Piano Artist” alongside other genderqueer performers.[20] Despite her continued artistic success, her California performances during this period were reportedly less provocative and more subtle than those of her youth in Harlem.[21]

“Cured”?

Bentley’s fortunes, and the social and economic pressures surrounding her, changed dramatically in the post-war period. By 1950, the creeping backlash against queer Americans and public expression of queer identities had become enmeshed with other developments – particularly the advent of the Cold War. What had been mounting suspicion of the queer community in the 1930s and 40s became something far more dangerous after the midcentury turn: a fully-fleshed political movement targeting queer public figures (visible, closeted or suspected) perceived as dangerous to US national security.

The Lavender Scare of the 1950s came amid a wave of queerphobic backlash and repression in the post-World War II era (Evening star. [volume] (Washington, D.C.), 25 May 1950. Chronicling America: Historic American Newspapers. Lib. of Congress)

The subsequent “Lavender Scare”, named to mimic the Red Scare that produced it, saw Senator Joseph McCarthy lead a federal government effort to purge suspected queer Americans (specifically gay men employed by the federal government) from positions of influence.[22] Unlike the Red Scare, the Lavender Scare saw thousands harassed, targeted and in many cases outright fired from their jobs over a period of several years. The unholy crusade against queer federal employees and service members reverberated throughout the US – from DC to New York to Hollywood – and deepened a wider moral panic around the prevalence of queerness throughout the country. Per Judith Adkins, an Archivist at the US National Archives, “greater public awareness of homosexuality coincided with growing unease and, in many parts of the country, an increase in official repression.”[23]

Firings, arrests and harassment of queer Americans became commonplace amid Cold War era social politics

Such was the environment which Bentley faced in the early 1950s. As a Black woman who had been an openly queer public figure for decades, she was subject to an especially intense and insidious pressure to revamp her image to suit the changing environment. It is also probable that she recognized the risks to her career, and perhaps safety, apart from a convincing rebrand.

In August 1952, Bentley published an astonishing article “I Am A Woman Again” for Ebony magazine which read as a wholesale repudiation of her former queer identity.[24] Therein, among other claims, Bentley suggested that a doctor’s intervention in her life (via hormonal drugs) had reignited her feminine nature. “Cured” (in her words) of her lesbianism and previous gender ambiguity, she claimed to have married a man named J.T. Gibson – who immediately disavowed any such relationship with Bentley.

Nevertheless, Bentley was indeed married to a cook named Charles Roberts almost simultaneously to the article’s publication (although this marriage may have been hastily arranged, and Roberts was notably just 28 while Bentley was nearly 45).[25] The Ebony article was completed by very pointed photographs of the reformed Bentley, “wearing a matronly white housedress and performing the role of homemaker—preparing meals, making the bed for her husband, wearing a dress and flowers in her hair.”[26]

In the 1950s, Bentley undertook considerable efforts to transform her public image to match the gender roles of the day (Image credit: Queer Music Heritage)

After “Again”

The “I Am A Woman Again” article raises an array of questions, but perhaps most prominently: was Bentley’s supposed transformation genuine, or was it simply a clever career move by a seasoned professional? Of course, it is entirely plausible that Bentley meant every word of her article, and that her comments reflected her diverse experiences of life until that point in a sincere manner.

Unfortunately, Bentley died of pneumonia in 1960 after a brief restart of her musical career, passing at the relatively young age of 52. Ironically, the 1960s would represent the beginnings of the queer liberation movement in the US (with the Stonewall Riots a crucial touchstone in 1969), as well as the transformative years of the Civil Rights Movement. Bentley’s perspective on these movements and the changing views toward queer Americans (given her own history) would have been fascinating indeed. However, such perspectives were unfortunately rendered impossible by her untimely passing.

As ever, context is always important to interpreting primary source documents. Historians have their own views on Bentley’s legacy – starting with the famous article itself. As one analysis argues, “[a]lmost every scholar who has examined Bentley’s life agrees that she published the Ebony article to escape persecution during the McCarthy Era and the Lavender Scare,” adding that the article contained strange references to lesbian literature and multiple factual errors (such as the veracity of Bentley’s supposed marriage to Gibson).[27] Financial incentives, though, were perhaps another key factor in Bentley’s reinvention. Notably, Bentley signed a recording contract with a label called Swingtime in 1952 – the same year as the “I Am A Woman Again” article was published.[28] She reportedly abandoned her drag king attire permanently thereafter and performed in dresses and “feminine” traditional outfits (similar to those she wore for the article’s photos).

The movement for LGBTQIA+ rights gained momentum after Bentley’s lifetime following the repressive politics of the 1950s (Image Source: New York Public Library)

Likewise, there may have been a religious aspect to these radical changes in Bentley’s life. She was believed to be studying for ordination to a ministry role around the time of her passing. Her article certainly makes religious allusions, and other sources suggest that leaders within the Black church may have been among those who put pressure on Bentley to adopt a more traditional lifestyle.[29] The Black church in America was, during the 1950s and 60s, the powerful driving force of the Civil Rights Movement with enormous influence among Black Americans throughout the country. A call to change from these quarters might have had a particularly deep resonance for Bentley.

Taking all of this together, Bentley was perhaps not fundamentally “changed” but rather made a conscious choice to disavow her identity for multiple reasons – and then did her best to make the new public image stick. This view, interestingly, matches with the robust body of evidence in the 21st century that the “ex-gay” and “conversion” movements are overwhelmingly failures (and remain discredited by medical institutions).[30] All of these complex factors surrounding Bentley’s final years of life make her passing all the more tragic, raising questions that are perhaps unanswerable and even unknowable decades later.

Renaissance Legacy

It is impossible to neatly summarize the legacy of a larger-than-life persona like that of Gladys Bentley. A Black and queer icon of the Harlem Renaissance age, who seemingly repudiated her former self, represents a complicated narrative indeed. While it is tempting to focus solely on her youth as the queer musical star of New York City, to do so would be to minimize the very real oppression she experienced as a performer facing multiple forms of marginalization throughout her life. To what extent said oppression influenced her actions in her later years remains unclear.

What is undeniable, however, is that Bentley (for at least a time) was an unabashedly Black and queer American celebrity in a country which still resented all of who she was. In this sense, Bentley can be viewed as a trailblazer for the Black and queer performers to come – both in the adulation, and the challenges they continue to face today.


[1] Steven W. Lewis, “The Harlem Renaissance in Black Queer History,” National Museum of African American History and Culture, May 28, 2022, https://nmaahc.si.edu/explore/stories/harlem-renaissance-black-queer-history.

[2] The National Museum of African American History and Culture, “A New African American Identity: The Harlem Renaissance,” accessed December 27, 2023, https://nmaahc.si.edu/explore/stories/new-african-american-identity-harlem-renaissance.

[3] Isabel Wilkerson, “The Long-Lasting Legacy of the Great Migration,” Smithsonian Magazine, September 2016, https://www.smithsonianmag.com/history/long-lasting-legacy-great-migration-180960118/.

[4] The National Museum of African American History and Culture, ibid.

[5] Ibid.

[6] Lewis, ibid.

[7] Giovanni Russonello, “Gladys Bentley,” The New York Times, January 31, 2019, https://www.nytimes.com/interactive/2019/obituaries/gladys-bentley-overlooked.html.

[8] Ibid.

[9] American Masters (interview), “Gladys Bentley: Gender-Bending Performer and Musician,” June 3, 2020, PBS, https://www.pbs.org/wnet/americanmasters/gladys-bentley-gender-bending-performer-and-musician-i0xlo0/14597/.

[10] Russonello, ibid.

[11] National Museum of African American History and Culture, “Gladys Bentley,” accessed December 28, 2023, https://nmaahc.si.edu/gladys-bentley.

[12] Lewis, ibid.

[13] Haleema Shah, “The Great Blues Singer Gladys Bentley Broke All the Rules,” Smithsonian Magazine, March 14, 2019, https://www.smithsonianmag.com/smithsonian-institution/great-blues-singer-gladys-bentley-broke-rules-180971708/.

[14] Lewis, ibid.

[15] National Museum of African American History and Culture, “Gladys Bentley,” ibid.

[16] Shah, ibid.

[17] Discography of American Historical Recordings, s.v. “Bentley, Gladys,” accessed December 28, 2023, https://adp.library.ucsb.edu/names/107258.

[18] Russonello, ibid.

[19] Ibid.

[20] Advertisement in San Francisco Life, December 1942 (via The Museum of the City of San Francisco, accessed December 28, 2023, http://sfmuseum.org/hist10/mona.html).

[21] Shah, ibid.

[22] Judith Adkins, “’These People Are Frightened to Death’: Congressional Investigations and the Lavender Scare,” Prologue Magazine (Publication of the National Archives), Summer 2016, Volume 48, No. 2, https://www.archives.gov/publications/prologue/2016/summer/lavender.html.

[23] Ibid.

[24] Lillian Gieseke, “Gladys Bentley’s Confessions,” Sapientia (Publication of the Center on Religion and Culture at Fordham University), August 4, 2022, https://crc.blog.fordham.edu/arts-culture/gladys-bentleys-confessions/.

[25] National Museum of African American History and Culture, “Gladys Bentley,” ibid.

[26] Shah, ibid.

[27] Gieseke, ibid.

[28] Russonello, ibid.

[29] American Masters (interview), ibid.

[30] Victoria Whitley-Berry and Sarah McCammon, “Former ‘Ex-Gay’ Leaders Denounce ‘Conversion Therapy’ In A New Documentary,” PBS, August 2, 2021, https://www.npr.org/2021/08/02/1022837295/former-ex-gay-leaders-denounce-conversion-therapy-in-a-new-documentary.