Film / TV

The Diva Will Succeed: HBO’s “The Stroll” Documents the Lives of Trans Sex Workers of the Pre-Sephora Meatpacking District in Their Own Words

Co-director Kristen Lovell in “The Stroll,” directed by Lovell and Zackary Drucker (Photograph by Samantha Box/HBO)

I’ve recently been suffering from a bad case of documentary intolerance. If I see another talking head, I’m going to puke! This sudden allergy to all things doc is a condition I developed as every streaming service has become bent on churning out an endless excess of hashed-out, shoddily produced documentary films or docuseries on any and every subject with even a whiff of a scandal or a pinch of public interest. Too many docs, too little time, often appearing way too fast after a luridly captivating media frenzy. I’m just waiting for the inevitable announcements about the upcoming docs on the Oceangate Titanic submergible saga. My physical aversion to documentaries has become so acute and insurmountable that I haven’t even been able to press play on the ones recently released about role models I revere like Donna Summer, Little Richard, and Anna Nicole Smith.

However, I may have discovered an antidote to my anti-documentary ailment: films that are made with such palpable care and empathy that it’s impossible not to be moved by them, that are not exploitative despite being about subjects that could be easily exploited, and that leave room for complexity rather than present one-sided dumbed-down one-note conclusions. This revelation came courtesy of The Stroll, an HBO documentary that was released last week and is currently streaming on Max. Directed by Kristen Lovell and Zackary Drucker and produced by Matt WolfThe Stroll focuses on the lives of trans sex workers who walked the cobblestone streets of the Meatpacking District way before it transformed into today’s bland landscape of Sephoras, Apple stores, Starbucks Reserves, bottomless brunch restaurants, and various expensive food markets populated entirely by baffled tourists who look as confused as I am as to why they’ve chosen a sandwich shop as a destination on their sightseeing excursion around Manhattan.

Even with the increasingly social justice-inclined stance of many streaming services and production companies (which don’t seem to have extended this stance to paying attention to their writers’ demands but regardless…), the subject of sex work in the golden age of New York City sleaze could effortlessly have turned into a lugubriously voyeuristic tale. Think the early days of Law and Order: SVU: sex, drugs, and skimpily dressed sex workers leaning into johns’ cars over a slick of butchered cow fat on the streets. Certainly, many before The Stroll covered this topical territory by doing just that. A clip played within the documentary from a RuPaul segment on Manhattan Cable acts as prime evidence. Stomping around The Stroll, Ru doesn’t take the reality of the sex workers’ lives—the homelessness, the difficulty of transitioning, the exclusion from other means of working—seriously. Instead, she cackles and complains about doing man-on-the-street interviews: “I had to be friendly with them and that’s hooking in a sense, so what’s the difference? It’s almost the same.” “Ru should have known better…” comments co-director Kristen Lovell.

Of course, fracking fanatic Ru is no stranger to being a gay villain and it’s worth noting that her segment was made in a different time (as was Ru’s song “Tranny Chaser”). Yet, the clip still comes off as spectacularly ignorant. And presents a compelling contrast with the empathy shown within The Stroll, spearheaded by co-director Kristen Lovell, who formerly worked as sex worker on The Stroll herself. A lot of loud, heated arguments have been made recently about who can and should tell certain stories. Like most debates originating from the Internet, this discourse gets carried away most of the time and tends towards the needlessly prescriptive. Yet, that doesn’t negate the fact that who tells certain stories matters. The Stroll provides a perfect example as Lovell acts as the documentary’s emotional core by not only telling her own story but encouraging others to share theirs with a sensitivity that only comes from also having been there.

The documentary opens with Lovell recounting her own entry into sex work after being fired from her job at a coffee shop once she started her transition. At that time, there were no protections for trans people against discrimination in the workplace so sex work became one of the only options for survival (As Lady P observes, “People were not hiring people who looked like me. Girls did what they had to do”). Sitting with co-director, artist Zackary Drucker, Lovell watches and comments on a clip of herself from an earlier documentary produced while she was still working The Stroll. She describes how the experience of being a subject in a film drove her to not only pursue filmmaking but, with an interest in the history of trans women in sex work, convey the complicated reality of her—and others’—experiences. As she says, “I felt that I could get it right if I was the one to tell it.”

And she’s correct—she is the one who needed to tell it. This becomes immediately clear in the aired pep talk Lovell provides to a handful of interviewees. For instance, to sequin blazer-sporting Cashmere, she kindly says, “I want you to be comfortable—your regular self. It’s just me and you having a conversation and telling your stories.” While some may question the necessity of leaving in this preparatory footage, to me it feels like an essential declaration about process: how to create a sense of support and safety when you’re asking people to discuss lives that are as precarious as trans sex workers of color rather than solicit people’s stories for the benefit of your own ego, career, narcissism, or yearning for publicity from a position of power.

Trans sex worker on the stroll (1980s) (Photograph by Jeffrey M Levine/HBO)

It’s exactly this care that allows the interviewees, some of whom worked The Stroll for over twenty years, to shine. While a few of those featured are familiar public figures and activists such as G.L.I.T.S’s Founder and Executive Director Ceyenne Doroshow, the Overall Godmother of the House of LaBeija, Egyptt LaBeija, and Transgender Equity Consulting’s Cecilia Gentili, the film only credits each subject by their first name, which democratizes their voices without empathizing the more well-known over others. Each girl, as they lovingly refer to one another, comes off as charismatic with a good sense of humor (“I hope their tires BUST!” Ceyenne quips about a distant police siren) without shying away from the uglier realities they confronted.

Through their experiences, Lovell and Drucker are able to tell a wide-ranging story that covers everything from the empowerment and life-affirming motivation of seeing other strong, Black trans women (“I want to do this. This is me!” exclaims Carey) to the danger, as in Elizabeth’s experience, of being bashed by clients and subsequently turned away from nearby St. Vincent’s Hospital; from the long-held friendships built on protecting each other in dark alleyways (Nicole: “When people say there’s no honor amongst hoes, they told a fucking lie. The Stroll, for us back then, was nothing but honor and protect the girl who was in that back street”) to the exploitation by police who would, at once, solicit them and arrest them; from the downturn of their clientele post-9/11 to the rise of Internet chatrooms as a source of income and better client screening. There are many losses here, whether the loss of lives such as the murder of Amanda Milan, who bled out in front of a crowd at Port Authority, or the losses inherent in gentrification supported by the Bloomberg-era Operation Spotlight policy, which sent a lot of the girls to Rikers, making way for the Meatpacking District we know now. As Egyptt says, referencing previous docs, “A lot of times they cut out the good parts or the true meaning of what we had to go through. Some of it was traumatic. Some of it was happy. Some of it was sad.” The Stroll encompasses it all.

Certain themes, however, stand apart. Gentrification looms large in The Stroll with the rise of broken windows policing with Rudy Giuliani and the aforementioned Operation Spotlight during the glass tower Bloomberg years. It is tough in 2023 to recall—or even simply believe—that at one point Giuliani was not only functioning but ruthless. It’s not just the mayors though. Some of the strangest pushback against sex work came courtesy of the West Village neighbors who rallied to snuff it out by hanging enormous insulting banners and creepily jotting down johns’ license plates so they could later call to threaten them. The funniest part is that these pearl-clutching neuter neighbors such as resident interviewee Harry felt as if they were victims of something!

(From left) Director Kristen Lovell and film subjects Stefanie and Elizabeth in “The Stroll” (Photograph by Courtesy of HBO)

Yet, more than the talking heads brought in to discuss the inherent destabilizing displacement of gentrification, the film best asserts this evolving reality simply through the footage of Lovell and others strolling around contemporary 14th Street. That about says it all. So does one of my favorite parts, which features Lady P and Brenda, who the closing credits sweetly note have been friends for over 35 years, revisiting the locations of moody and glamorous black-and-white photographs taken of them during the “film noir” years of the Meatpacking District. They still find certain areas of ruptures in the landscape of the redeveloped Meatpacking District about which to reminisce, whether unlocked trucks or a desolate parking lot. Yet, even in the footage of the various subjects wandering around the ritzy high-end neighborhood, there is a distinct note of ambivalence that the directors don’t shy away from. It’s hard to wax poetic about the bygone days when so many of the girls died. This is even further cemented by an emotional moment when Cashmere breaks down, crying in Lovell’s embrace, about “the things we had to do.” “I hate this place,” Cashmere says, which dismisses any easy romanticization of pre-gentrified NYC.

It’s also not as if gentrification completely erased or banished communities of queer and trans, mostly homeless, communities from gravitating towards Manhattan’s west side. In this, The Stroll would make a pitch-perfect double-feature with Elegance Bratton’s 2019 documentary Pier Kids, which traces similar stories and themes amongst queer and trans youth of color who—at least at the time of filming in 2011-2012 and 2016—frequent the Christopher Street piers. We see the young stars of Pier Kids in real-time as they deal with transphobic family members, sex work, police intimidation, and friends’ deaths. Contrasting with The Stroll, they are not looking back from a perspective of the relative comfort of more stable situations.

However, it’s not as if this short distance lessens the impact. Overall, The Stroll expertly portrays the precarity of the lives of trans sex workers of color, seen most devastatingly in the lack of elders in the community (Egyptt remarks on this devastatingly by pointing out that just about five girls are still alive from around a thousand on The Stroll in the 1980s), juxtaposed with the support they forged amongst themselves. This doesn’t mean that the elders don’t continue to inspire even from beyond. Unsurprisingly, Sylvia Rivera emerges through the documentary as, at once, a predecessor, a godmother, and a patron saint. The film includes the now much-repeated footage of Sylvia iconically spewing bile at the 1973 Christopher Street Liberation Day Rally as white gays and lesbians shoved aside the trans community and pioneers like Rivera, who fought for gay rights at her own expense. Why did they turn their backs on Sylvia? In order to gain mainstream acceptability, of course! An impulse that we see happening yet again as trans activists are being blamed for the decrease in LGBTQ+ acceptance, a blame game perhaps stated most clearly in a recent, wildly biased article “Why Pride Lost the Public” in The Spectator.

The eight annual Trans Latinx March in “The Stroll” (Photograph by Erik McGregor/HBO)

More than just a hoarse voice shouting into the abyss, though, later footage of Sylvia is perhaps more poignant. In these clips, viewers see Sylvia giving a tour around the shantytown/tent city she built on the Hudson (near where David Hammons’s hideous Day’s End scaffolding is now), which The New York Times branded “The Shantytown of the He-She’s” (we should remind them of this). While clearly living hand-to-mouth in these dilapidated, ramshackle structures, Sylvia would welcome homeless queer and trans people to stay with her knowing they’d be safe there. Though older and clearly fallen on even harder times, Sylvia in these later clips has no shortage of that same fire as she did in 1973, railing about the “damn shame” that only 200 people, notably those within the sex worker community, showed up to the action after Amanda Milan’s murder.

Amanda Milan’s murder is also a central rallying point. The Stroll rightfully contrasts the response to Milan’s death with the outpouring of rage and grief after the murder of Matthew Shepard just a few years before. It’s enraging to think about the lack of concern for those who even mainstream gay society considers expendable. Yet, Milan’s death did at least motivate the community of trans sex workers to begin advocating for themselves with renewed vigor. This activism concludes the documentary on an encouraging note without laying the cheese on thick, largely centering on the repeal of the Walking While Trans laws, which attempted to spot sex workers by fixating on loitering or behaviors thought to be related to prostitution that often simply amounted to existing as a trans woman of color in public.

It’s refreshing that the documentary keeps its eye trained on the issues and legislation specifically related to trans sex workers rather than attempting to shove in each and every trans-related controversy, Don’t Say Gay bill, drag brunch scare tactic, book-banning horror, women’s sports fiasco, pronoun throwdown, groomer slander, or any other option in the litany of new culture war flashpoints in an attempt to be as relevant as possible. That would have resulted in the muddying of the waters in an attempt to solve it all, which is the Achilles heel of a lot of activism. Instead, The Stroll maintains its focus on a population that is one of the most at risk. These histories are not easy to tell or to watch (more so than The Stroll, Pier Kids has some tough moments). Yet, The Stroll reminds us exactly why they are essential, particularly as the impulse towards respectability politics has reared its head yet again, which will inevitably give way to moralizing that will seek to shove those like sex workers back to the margins. All the more reason for those with these experiences to keep documenting them.

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