Noah Griggs 11/20/25 Noah Griggs 11/20/25

The Roots of TDoR | Rita Hester (1963-1998): Not Just Cistory

Content Warning: this post includes semi-graphic descriptions of violence against a Black trans woman, police incompetence, and transphobia, a second notice will be given at the second where these topics are discussed

Gwendolyn Anne Smith and Penni Ashe Matz created Transgender Day of Remembrance (frequently abbreviated as TDoR), but there is another woman to whom respect and honor is due on this day in particular. It was Rita Hester's death, and the reaction to it by both the general public and the LGBT+ community at large, that had that inspired the two activists to found the holiday which has been celebrated every year since 1998 (Riedel, 2022).

Part of my heart breaks to write about Rita Hester in the context of TDoR, as there is so much more to her than her death, as there is for any person. I will endeavor, as I always do, to share information about her than just the piece that she is most known for.

An Early Life of Love

Rita Hester was born on November 30th 1963 (Sosin, 2020). She'd be 61, almost 62 at the publication of this blog post, were she still alive. Even from a young age Hester was an individual who was very feminine. Her sister described Rita's identity as known and accepted by the entire extended family (Sosin, 2020). She was surrounded by love and acceptance from birth.

As Rita grew, however, it become more and more evident that Hartford, was not the place for her .As "a Black trans woman... [Hester] chafed against the expectations placed on her by her surroundings" (Riedel, 2022). "'In Hartford, people got assaulted and got hurt and all the other stuff'" (Sosin via Hester, 2020), and understandably, that was not an ideal living situation.

Like so many other trans folks both before and after her, she looked towards cities to find a more accepting atmosphere. "[A] hundred miles away in Boston, there were parties and rock clubs where it didn’t matter that she was trans" (Riedel, 2022) and, in Boston, Rita thrived.

Finding her Place and Spreading her Wings

Enamored with Boston's queer community, "In her early twenties, Hester moved north permanently to Boston’s Allston neighborhood" (Riedel, 2022). It was 1988 and the city was her oyster (McNaught, 1998, p. 25). Here she found a second family; one that spanned both the queer and straight communities.

A Boston Phoenix article published less an month after Rita's murder begins with "Hester's friends have different perceptions of what the 34- year-old was like, but they all agree on one thing: 'The girl could dance!' Hester, they recall, was an incredible entertainer whose dance shows... [from] four years ago are still talked about. Glossy black waist-length braids. Voluptuous candy-apple-red lips and eyelashes so long they could almost create a breeze. Hester was six foot two and weighed about 200 pounds, but her friends say she was as agile as a tiny dancer. And she lit up a room with her warm, boisterous greetings"(McNaught, 1998, p. 21). Her friends said that "Hester lived large and loved big" (Sosin, 2020). Given how she was remembered by her community, it is clear that Hester was a vibrant soul that brought so much life and joy to the communities that she was a part of.

Living her own Life

Rita did not let herself be confined to the queer bars and clubs of Boston; she patronized bars in both the 'straight' and 'queer' parts of Boston. "One of Hester’s friends in Boston, Jessica Piper, remembered her as the only link between the city’s queer bars and the decidedly hetero nightlife uptown. 'The other queens wouldn’t go out to Allston from fear...and the straight Allston kids didn’t want to go to downtown queen bars' (Riedel, 2022)". Hester did not limit herself in how or where she could enjoy life, and undoubtedly, her life was richer for it.

Hester having a foot in each world was worrying to those closest to her in the trans community. They understood that Rita, while pretty, vivacious, and friendly, she was not entirely safe in the world that so rigidly adhered to the gender binary and cissexual expectations (Sosin, 2020). It was at one of these straight bars that she met her best friend; Brenda Wynne. She was "a white cis woman who called Rita her 'best friend in life'... [and they] shared a deep bond..." (Riedel, 2022). It was not all danger and ostracization from those that lived in the 'straight world', Rita found connections and community there as well.

Hester lived her life on her own terms, earning money as a sex worker and a dancer (McNaught, 1998, p. 23). Rita was also "deeply embedded in the city's rock scene" (Sosin, 2020) and "[she went] from attending shows in rock clubs to performing and dancing in them" (Reidel). She was so talented, that she performed internationally, traveling as far as Greece and Germany to dance (McNaught, 1998, p. 25). Rita was a talented woman, and was able to make a living off of her skills as a performer.

Her Life Cut Short

Content Warning: this next part includes semi-graphic descriptions of violence against a Black trans woman, police incompetence, and transphobia

The first to notice that things were not as they should be on the day that Hester was murdered were those closest to her. Friends, one of whom was Wynne, realized that Rita wasn't meeting up with them, as planned (Sosin, 2020). Later that evening, Hester was seen to have had "an altercation with a man at the bar who followed her out when she left.... others report[ed] that Hester went from Silhouettes to the Kells before going home. According to neighbors, two men were seen coming out the back door of Hester's apartment later that night" (McNaught, 1998, p. 25). Some of those in Rita's community and were concerned about things they saw happening that night, though they could not have known what the larger context and danger were.

The information from the police and their response is detailed and clear, but gives no answers, and little context. "Officers responded to a call about a fight at Rita's address at 6:12 p.m... and were dispatched 7 minutes later... When they found Hester, she was still alive on the floor. She had been stabbed repeatedly in the chest... More than an hour passed between the time police were dispatched and an ambulance took her to Beth Israel Hospital, where she died of cardiac arrest" (Sosin, 2020). The scene itself is almost too horrible to imagine. There had to have been blood everywhere, not to mention Rita was still fighting for her life, even if the attacker had fled.

While the police report does acknowledge that she was stabbed repeatedly, but what it leaves out is that "a brutal stabbing of this nature is evidence of a very personal killing" (Munroe, 2015). Was the killer a client of Rita's, or someone she knew personally? Evidence suggests that it was someone who knew Rita, since "there was no evidence of forced entry and nothing was stolen" (Munroe, 2015). Clearly, robbery wasn't the motive, and she must have let them in.

Then, there's the fact that Rita was a transgender woman. "Such frenzied damage is a common feature in many murders of transwomen, usually indicating shame and other emotional turmoil on the part of the killer" (Munroe, 2015). The earliest information made public about her murder would have left you not knowing that the murder victim was a transgender woman, unless you knew Rita personally.

Media Misstep

The news coverage about Rita Hester's murder followed the pattern that many of us are familiar with. Her gender, name, and pronouns were not reported on correctly. In short, her identity was not respected, and that aspect of the crime was lost in the reporting. It was initially reported that " a man who was also a transvestite had been stabbed to death" (Nangeroni, 1999).

Boston Globe reported Daniel Vasquez described Hester in an article "as a 'nightclub singer and a party-thrower, a man who sported long braids and preferred women’s clothes.' He also referred to 'Hester’s apparent double life,' and used male references for Rita throughout the story" (Nangeroni, 1999). It was clear that the media and police force were not interested in who Rita was, and how that may factor into her killing.

There was an article written for The Boston Pheonix soon after Hester's murder, remarking on the outcry about the incorrect description of Hester in the media. The article's author quotes multiple people who insist that the murder is more important than how she was described in the media immediately after her death. One of which particularly leaves a bad taste in my mouth. Jeff Epperly, the then editor of Bay Windows was quoted saying that "he too, believes the main issue is that someone was brutally murdered" (McNaught, 1998, p. 23). On the surface this makes sense, and I agree. Her being killed, and the killer going without being caught is a big issue. However, his quote continues with "'If we were writing a feature piece, we would go with [the gender identification] the subject wanted... but this is the news, and we have to deal with the facts. And the fact, according to police records is that the victim was biologically a male'"(McNaught, 1998, p. 23). This, to me, is a frustratingly uncritical way to look at the press surrounding Rita Hester's murder.

Now, I don't know Mr. Epperly, and I have used this new article as a source in this blog post beyond this part, because I do believe that it is a useful contemporary source. However, it is a perfect example of the lack of respect afforded to trans people, particularly trans women, and trans folks of color who tragically make up the majority of trans folks who are attacked and killed in the United States each year (Sosin, 2020). If we cannot do something as simple as describe the victims accurately then what hope is there for getting them justice? Yes, solving the crime of her murder is important, but Rita Hester also deserves to be respected and described as who she was, and not by the assumptions made by the police, and then parroted and defended by the media.

Transgender Day of Remembrance & Recent Years

On the one year anniversary of Rita Hester's death, a handful of Transgender activists joined together to remember and name all of the transgender individuals who were murdered in the past year. This was the first Trans Day of Remembrance.

Many folks who were aware of other anti LGBT+ hate crimes and murders and their victims could not name Rita herself (Smith, 2012). The founders of TDoR, as well as Hester's family and community felt that the public's response reflected the "disregard police and media show for Black transgender murder victims" (Bedford & Sosin, 2023). Rita deserved to be remembered correctly and respected, as do all transgender individuals.

In 2023 a new detective was assigned to Hester's case, and on the 28th of November of that year, they renewed their search for her killer (Bedford & Sosin, 2023). This time Rita's name and identity will be respected during the investigation. This is good news as "The average clearance rate for murders with transgender victims from 2010 through 2020 was about 48%, ...The national average murder clearance for that same time period was roughly 62%...[and] The disparity is even greater in cases where police have deadnamed or misgendered victims" (Lantz via Bedford & Sosin, 2023). We can only hope that with the correct questions being asked, some answers will be found, and some closure, if there is any to be had, can be given to Hester's family and loved ones.

Remembrance is Necessary: Conclusion

Rita Hester was a vibrant, talented woman, who lived her own life to the fullest, and should have been been able to live a long and fulfilling life. She was brutally murdered by someone who knew her, and hated her, most likely simply for being transgender. Then, in the wake of her death, she was disrespected repeatedly not only by those who reported on the crime that ended her life, but also those that were supposed to be solving the crime.

Today, Rita's legacy lives on in the lives she touched, but also in Trans Day of Remembrance. We remember those who have died from violence against trans people. The remembering is an essential part of the work that we do to work to create a better future. We cannot build something new if we don't understand where we have come from.

The original painting featured in this blog is available for purchase, and Rita Hester, and her story, are featured in the first collection of my Ancestor Cards.

NOTE! Some links (those with an * next to the name) are affiliate links. I will receive a small commission if you use these links to purchase something. It will not change the price of the product for you.

References

Bedford, T., & Sosin, K. (2023, December 4). Boston police recommit to solving murder of Rita Hester, whose death inspired Transgender Day of Remembrance. GBH. https://www.wgbh.org/news/local/2023-12-04/boston-police-recommit-to-solving-murder-of-rita-hester-whose-death-inspired-transgender-day-of-remembrance

McNaught, S. (1998, December 11). Displaced Anger: Is Rita Hester’s murder being eclipsed by the transgender community’s grammatical agenda? The Boston Phoenix December, 21, 23, 25. https://ia601809.us.archive.org/19/items/sim_boston-phoenix_december-11-17-1998_27_50/sim_boston-phoenix_december-11-17-1998_27_50.pdf

Munro, D. (2015, November 19). Grieving lives lost without reason on Transgender Day of Remembrance. WHYY. https://whyy.org/articles/grieving-lives-lost-without-reason-on-transgender-day-of-remembrance/

Nangeroni, N. (2025). Rita Hester’s Murder and the Language of Respect | GenderTalk. Gendertalk.com. https://www.gendertalk.com/language-of-respect/

Riedel, S. (2022, March 31). Remembering Rita Hester, Who Changed What It Means to Remember Trans Lives. Them. https://www.them.us/story/rita-hester-trans-remembrance-visibility-memorial

Smith, G. A. (2012, November 20). Transgender Day Of Remembrance: Why We Remember. HuffPost; Huffington Post. https://www.huffpost.com/entry/transgender-day-of-remembrance-why-we-remember_b_2166234

Sosin, K. (2020, July 17). Her death sparked Transgender Day of Remembrance. 22 years later, still no answers. NBC News. https://www.nbcnews.com/feature/nbc-out/her-death-sparked-transgender-day-remembrance-22-years-later-still-n1233809

Noah Griggs 9/16/25 Noah Griggs 9/16/25

A Shooting Superstar | Holly Woodlawn (1946-2015): Not Just Cistory

We have told the stories of several trans women in the Not Just Cistory series that achieved the life they wanted for themselves by conforming to the gender expectations of women at the time and blending in with the women around them. There is nothing wrong with this, and is still something many trans folks (both men and women) do today. Holly Woodlawn, on the other hand, was not interested in blending in, in any sense of the word.

A top-down photo of a gouache painting of Holly Woodlawn, a Puerto Rican woman with a pale complexion. She's wearing a red wig and large dangly gold earrings. The painting is resting on a pink silk piece of fabric with jewelry around it.

Early Life

Holly Woodlawn was born in Juana Diaz Puerto Rico in 1946 on October 26, to a Puerto Rican mother, and a German-American father (Grimes, 2015). She described “the culture [as] more Caribbean. Everyone's naked, it's hotter, you come out earlier. I was having sex when I was seven and eight in the bushes with my uncles and cousins - of course, they were only 11 or 12 themselves. I was raised in a house full of women and my uncle was gay. We lived in a little tiny town, so those were my role models” (Paterson, 2007). Her time in Puerto Rico was an essential foundation to her identity and sense of self in terms of her gender.

Woodlawn didn’t live in Puerto Rico long. She left in 1955, when she was 9, with her mother. They moved to New York, where her mother met and remarried, to a Polish-Jewish immigrant named Joseph Ajzenberg, who adopted Woodlawn as his child (IMDb & Sieger, 2015). Her time in New York, and later Miami, Florida, were not particularly happy times for Woodlawn. She was uncomfortable in her middle-class suburban life, and felt as if she didn’t know who she was (Patterson, 2007). Suburban stability painfully constricted a young Holly Woodlawn.

Her teen years were a prologue to the rest of her life. She made a copy of her father’s car keys and would take his car to drive down to the gay beach and party (Russell, 2025). Her adolescent rebellion culminated in summer 1962, when she was supposed to be attending summer school to fix her failing grades (a result from spending too much time partying). She instead took the trajectory of her life even more into her own hands, and joined up with a group of Cuban Queens and sold some jewelry and made her way north to New York City (Patterson, 2007), where she was sure the rest of her life was waiting to begin.

However, her travels came to a halt like a bus at the end of its line when she ran out of money in Atlanta Georgia. She ended up hitchhiking the rest of the way north (Patterson, 2007). Woodlawn was living through the part of her life she would be most well known for, (but not the most interesting, in my opinion) though she had no way of knowing at the time. Despite all her ambition, adventures, and accomplishments, Holly Woodlawn was most known, both during her life, and now after her death, as the ‘Holly’ in Lou Reed’s song ‘Walk on the Wild Side’ and as a Warhol Superstar. Her verse chronicles her traveling to New York City to begin her new life.

Once in New York she had to create a new life for herself from scratch, and it was not easy. She took on a myriad of jobs to make ends meet. During this time she was also “a street-urchin in New York, a speed freak, a thief, a housewife, a go-go dancer, a beauty queen who was crowned Miss Donut in Amsterdam, New York, a floor model at Saks Fifth Avenue, a rioter at Stonewall, an Off-Broadway star, and a celebrated cabaret performer” (Copeland, 2025, p. 89). This hard-scrabble life was a continuation of living outside of the ‘normal' (normal meaning white, suburban, middle class) world that Holly had been attracted to her entire life. However, she had her sights set even higher in the heavens.

Into the Orbit of the Famous

Woodlawn wanted to be a part of Andy Warhol’s orbit, one of his ‘Superstars’. I am aware of the irony of interrupting the story of a trans woman to tell the story of a cis man, but knowing who Warhol was, is important to understanding Holly and her goals, so we will briefly diverge.

Warhol was a first generation Polish-American, whose parents immigrated to the United States (The Warhol). He “graduated from Carnegie Institute of Technology (now Carnegie Mellon University) in Pittsburgh with a Bachelor of Fine Art in Pictorial Design in 1949 and soon after moved to New York City to pursue a career as a commercial artist” (The Warhol). This was where he and Holly Woodlawn would meet.

Warhol worked as commercial artists for the first part of his career, but he is most known for his transgressive attitudes towards art, and his contributions to the Pop Art movement (the Warhol). His other paintings were often a critique of consumer culture, the iconic Campbell’s Soup cans piece, among them (Dupêcher, 2019) He continued, throughout his career, to paint commissioned portraits of the famous and elite individuals he became more and more involved with (the Warhol). Even this man, who adored the wild, avante garde life Holly desired, had his ‘safety net’. Many of the women he surrounded himself with did not have and could not create the same for themselves.

The other aspect of his creative endeavors was what Woodlawn was most drawn to, and entwined with; his films. He was a prolific film maker, and his “feature-length films that delved into New York’s underground subcultures and turned… [his] collection of artists and misfits into ‘superstars’” (Dupêcher, 2019), which was exactly who Holly wanted to be.

Her chutzpah was what initially attracted Warhol to her. During this time in the mid and late sixties, Woodlawn was acting in plays, and after one in 1969 when she was interviewed by a journalist, she proclaimed she was one of Warhol’s superstars (Grimes, 2015). Warhol heard about this and wanted to meet her. This sort of preemptive sort of connection is ironically similar to how Lou Reed wrote about her in “Walk on the Wild Side” (don’t worry, we’re almost to that part).

One Man’s Trash…

The project that made her an actual Warhol Superstar was the Paul Morrissey-directed Warhol film Trash, which was filmed in Morrissey’s basement (Patterson, 2007). Woodlawn, who was 23 by my math, was initially intended to just be in one or two scenes, but Morrissey loved her and her improvisations so much that she ended up filming for six days (Grimes, 2015). Holly is inextricably entwined with Trash. Much of her lines were self-created, and Woodlawn said that, along with the dialogue, even the clothing used as costuming was hers as well. She had been exactly where her character in the movie was (Grimes, 2015), and related to her intensely. For her efforts she was paid $25 per day, and she never received any money in residuals from Warhol (Copeland, 2025, p. 115).

Holly had finally made it; not only was she starring in one of Warhol’s movies, she was improving upon it! There was even an attempt by director George Cukor to nominate Holly for an Academy Award for her role in Trash but she was not considered. There are a plethora reasons floating around as to why she wasn’t, from the film being non-union (and the Academy did not, apparently, consider non-union films at the time) ( Woodruff, via Copeland, 2025, p. 164) to those in charge of making the decision could not decide on whether to categorize her as an actress or actor (Patterson, 2007). This must have seemed like her big break!

Is Another Man’s Biggest Hit

In 1972 Holly Woodlawn received a call from her friend telling her to turn on the radio. Confused, she told her that she didn’t have a radio (American Masters Digital Archive (WNET), 1997). This was how Holly found out she was the subject of the first verse of a new song; Walk on the Wild Side. She didn’t know Lou Reed, beyond attending the concerts he performed in (Patterson, 2007), yet the there she was:

Holly came from Miami, F-L-A

Hitch-hiked her way across the USA

Plucked her eyebrows along the way

Shaved her legs and then he was a she

She says, "Hey babe, take a walk on the wild side"

Said, "Hey honey, take a walk on the wild side" (Reed, 1972)

Each verse of the song describes a Warhol Superstar. The first is Holly, of course, then Candy, who is Candy Darling. ‘Joe’ references Joe Dallesandro, who was Woodlawn’s co-star in Trash Similarly, the ‘sugar plum fairy’ mentioned was the name of a character played by Joe Campbel (who dated Harvey Milk, coincidentally), and ‘Jackie’ is Jackie Campbell (Hann, 2015). Each of these individuals were queer and/or trans.

The fact that all of the subjects of “Walk on the Wild Side” were Warhol Superstars may seem like an incredible coincidence. At least, until one learns that Warhol was the mastermind, so to speak, behind the song. Penny Arcade (another Warhol actor) said that, Women in Revolt, another of his movies starring Woodlawn, “inspired Warhol to inspire Reed in his turn to write “Walk on the Wild Side”.... Warhol suggested it to Lou Reed because of the movie we were all in, Women in Revolt” (Moyer, 2015). “Walk on the Wild Side” was initially released as a single, but became a part of Reed’s album Transformer (produced by David Bowie) ended up being the biggest hit of his career (Trebay, 2013), and in a way he had Woodlawn and her contemporaries to thank for that.

After Warhol and Reed

1972 is the moment where the quantity of information about Woodlawn’s life decreases precipitously. At best you might get a vague sentence about her moving to California and starting fashion school, but that’s about it. Depending on when the article was written it may close out with the information regarding her death.

But, Holly was more than the men who featured her in their art. She lived an entire life outside of Warhol and Reed’s influence. She did indeed eventually move to California after Warhol’s death in 1987 (Patterson, 2007) but before that she “moved back home to live with her parents in Miami for several years before returning to New York and finding modest stage success as a club singer” (Villegas, 2021). She was determined to continue to carve out a life for herself in the way she found to be worth living, even if her time with Warhol had not granted her long-term fame.

After moving to Hollywood she continued to hustle just like she had on the east coast, refusing to give up. At this time she met Jeff Copeland, another struggling dreamer, who she became fast friends with. He ended up writing her biography with her, which was titled A Low Life in High Heels, and was published in 1991 (Villegas 2021). More recently Copeland has published Love you Madly, Holly Woodlawn: A Walk on the Wild Side with Andy Warhol’s Most Famous Superstar* which details his friendship with her in the 80s and 90s, including the time spent writing her memoir.

In 1989, at Copeland’s insistence, Woodlawn got a job at Wacko, “an eclectic collectible shop that sold battery-operated tin toys, Pee-wee Herman dolls, vintage Frankenstein models, thousands of fun postcards, and anything else that was kitschy, and retro-cool” (Copeland, 103). A fitting place to find an avant-garde superstar like Holly Woodlawn.

She also, during this time, decided to go to design school. In order to attend she had to get her GED (remember, she had dropped out of school at 15) and secure financial aid, but with those hurdles cleared, and the advance from her memoir, she was able to attend the Fashion Institute of Design and Merchandising (Copeland,182). She excelled at design, and enjoyed her studies (Copeland, 224). She considered creating a fashion line for transgender women after graduation (Copeland, 2025, p. 250). This was a wonderful creative outlet, and a chance to build something for herself.

These projects, along with the writing of her memoir helped keep Woodlawn’s life stable, for a time. Her literary agent sold the manuscript for A Low Life in High Heels to St. Martin’s Press for $40,000 US (Copeland, 2025, p. 174), which is almost $102,000 US today (CP Inflation Calculator). This success, combined with the whirlwind promotional tour in the leadup to the book’s publication certainly suggested that the pendulum of Woodlawn’s career was on the upswing.

The success of the memoir added to Woodlawn’s momentum. She was invited to party after exclusive party, and everyone in Hollywood knew who Holly Woodlawn was (Copeland, 2025, pp. 237-45). This was the life that Holly had wanted for herself ever since she first claimed to be an Andy Warhol Superstar, and she loved every minute of it.

However, the momentum began to slow as time passed. Both authors of A Low Life in High Heels wanted the book to be adapted as a movie, but they struggled to get the book in front of the people who could make that happen (Copeland, 2025, p. 250-251). Perhaps looking for more change, “Holy got bored with ringing up knick-knacks at Wacko. She had published a memoir now and was celebrated in the press. Working as a cashier just seemed so menial…. So [she] quit Wacko and got a job as a phone sex operator" (Copeland, 2025, p. 251). However, she “lasted a few weeks before she was fired for drinking on the job,” (Copeland, 2025, p. 215). If this were a novel instead of a woman’s life, it would be called foreshadowing.

Despite a lack of interest, hope for a movie deal continued, just as life did. In 1992, the trade paperback version of A Low Life in High Heels was released, and a friend of Holly's co-wrote a live television show for her to star in (Copeland, 2025, p. 259). Woodlawn also returned to doing cabaret performances across the US (Copeland, 2025, p. 259) continuing to find the spotlight wherever she could.

Suddenly, there was movement and “Madonna was in cahoots with a big producer and a world-famous writer to make a movie based on Holly Woodlawn’s autobiography…. The deal was being set up at Columbia Pictures through Dolly Parton’s production company…” (Copleand, 2025, pp. 261-262). This was just the sort of second wind that Woodlawn had been hoping for.

At this moment I must acknowledge that the bulk of the information being referenced during this portion of Holly’s life comes from Love You Madly, Holly Woodlawn*, and while this book does contain a wealth of information about Holly’s life during the 1980s and early 90s, it is from Jeff Copeland’s point of view, because not only is he the author, but it’s about his experience working and being friends with Holly Woodlawn.

At this point the two had a falling out over the screenplay rights. Jeff and Holly had agreed, at the outset of the writing of the proposal for A Low Life in High Heels, that Copeland would be the one to write the screenplay (Copeland, 2025). However, now Woodlawn, and their agent, wanted Jeff to relinquish that claim to the ’famous writer’ chosen by Madonna and the ‘big producer’ so that the deal could go forward (Copeland, 2025). Holly Woodlawn was a person for whom fame was always the end goal, so it may have seemed like a reasonable sacrifice, in the service of her life long goals.

Copeland did eventually relinquish the rights, and the deal with Columbia Pictures and Madonna went forward (Copeland, 2025, p. 266), reigniting the fire of fame surrounding Holly Woodlawn. “ [Madonna’s] name alone created a publicity firestorm for the book that went around the world” (Copeland, 2025, 271). Since she was once again famous, Holly decided not to pursue a job in fashion after she graduated with her degree. Her friends insisted that she was too famous to need a day job (Copeland, 2025, p. 272), and unfortunately, she listened.

Frustratingly, the movie deal fell through at the last second, “[t]here was a brouhaha amongst the producers that caused the entire deal to collapse” (Copeland, 2025, p. 273). This forced Woodlawn back onto the “cabaret circuit performing A Low Life in High Heels as a cabaret show in bars and clubs…” (Copeland, 2025, p. 275). She was back to what she had always done, hustling to get to where she wanted to be.

Eventually the hustling by both Jeff and Holly paid off, and in 1995 the movie rights were optioned by Michael Zoumas. This time Copeland was in charge of writing the script, along with director Rose Troche, but Holly was largely left out of the creative process of writing the script, which infuriated her. Proving once again the fickleness of Hollywood, this iteration never made it to production either. This was a pattern that continued for more than a decade (Copeland, 2025, p. 276-278). Woodlawn never lost hope that A Low Life in High Heels would be made into a movie, and continued to work towards that dream for the rest of her life.

Later Life

As Holly’s life continued on, her alcoholism worsened, and while she and Copeland were no longer close, he does give some insight into this part of her life. She lived, for a time “with a friend of hers in Beachwood Canyon… [in a house that was] so close to the Hollywood sign, it was almost in the backyard” (Copeland, 2025, p. 283). She had some stability, until, of course, the landlord sold the house and she was forced to move in with an acquaintance/romantic partner. After he was sent to jail for attacking Holly, she lived in that apartment for several years (Copeland, 2025, p.284).

Woodlawn’s flame of fame never really rekindled, though she “ had occasional cameo roles in films like “Billy’s Hollywood Screen Kiss” in 1998 and, in 2014, the Amazon television series “Transparent” (Grimes, 2015). She was always ready for new opportunities and adventure, even if they were becoming fewer and farther between.

Woodlawn’s health began to decline when she tripped and fell, damaging several nerves, and losing some of her ability to walk. She got sober at her doctor’s orders, but her health continued to worsen (Copeland, 2025, p. 284). The effects of a lifetime of drinking and drugs had too much inertia to be stopped now.

In a 2007 interview John Patterson describes Holly’s as “bent and frail, though indefatigably cheerful, using a Zimmer frame because of various slowly fusing discs in his spine that, he says, are unimaginably painful and incurable. ‘Oh no, this is IT, honey, downhill all the way from here on!’” (Patterson, 2007). (A note: Patterson uses he/him for Holly here, evidently because Holly was presenting masculinely that day.) Holly was still holding onto hope and her chutzpah despite her ailing health and lack of resources.

In 2015 Woodlawn was diagnosed with “terminal cancer that spread to her brain” (Copeland, 2025, p. 285). She professed a desire to return home to pass in Puerto Rico, and while that did not occur, she was provided for in her last month by friends and fans, who all contributed to an online fundraiser. She passed away on December 6th, 2015 at the age of 69 (Darling, 2019).

Holly was One of a Kind: Conclusion

Not only did Holly Woodlawn refuse to live a typical life, she refused to adhere to any gender expectations. She didn’t strive to be seen as a cis woman, and was open about her anatomy and fluidity with her presentation.

She was willing to change her presentation to suit the needs of the environment she found herself in. While she was living with her parents she presented herself as a man. Copeland said that when he picked Holly up from the airport once he hadn’t recognized at first, she had a crew cut and stubbled, not to mention she was wearing Bermuda shorts, sneakers and a polo (Copeland, 2025, p. 80). However, she also presented femininely for the vast majority of her life, and she had an eclectic sense of style as well as great skill in the application of makeup (Copeland, 2025). She might have been called a chameleon, given how completely she could change her appearance, except for the fact that the end goal was never to blend in.

Holly was very open about the gender affirming care that she had (or not ) received, though that was not what it was called in the 1960s and 70s. She had estrogen injections in the 1960s (Copeland, 2025, 93), but never had any sort of gender reassignment surgery (GRS). She didn’t feel the need to surgically alter her body, and she was more than willing to profess her love for her natal genitalia. “Holly loved having a cock. She told me so herself. The only reason she had ever considered a sex change in her youth was because the man she fell in love with wanted her to have it” (Copeland, 2025, p. 140). Woodlawn was an individual intimately comfortable with her body, and her identity, once she was able to carve a place for herself as an adult.

We could try to pin modern labels on Holly Woodlawn all we like, transgender/woman/vestite/sexual, genderfluid, agender, but the modern, rigid ways of thinking we seem to have boxed ourselves into would be a disservice to her. I think it is best if we just accept her identity for herself; “‘Darling what difference does it make if I’m a man or a woman? I’m Holly! Can’t those Motherfuckers understand that?’” (Woodlawn, via Copeland, 2025, 165). Holly Woodlawn’s story and identity are just as much a part of the time she lived in with the people who inspired her and she surrounded herself with, as it was her unwillingness to accept a role that didn’t suit her identity or her life.

Holly spent her life on a journey to fame that, for better or worse, she was unwilling to compromise on. That journey has become an inspiration to many trans folks, but “‘there was no role model for a Holly Woodlawn,’ said Penny Arcade, a fellow Warhol acolyte. ‘For Holly, whatever sacrifices she made in terms of acceptance of her family and society could never compete with the sense of freedom that Holly needed – the freedom to be herself’” (Moyer, 2015). She was truly a trailblazer, and even if it wasn’t the way she imagined, she definitely reached a superstar level of fame as a trans pioneer.

The original painting featured in this blog is available for purchase, and Holly Woodlawn, and her story, are featured in the first collection of my Ancestor Cards.

References

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Copeland, J. (2025). Love You Madly, Holly Woodlawn*. Feral House.

Darling, H.-H. (2019, December 16). Holly Woodlawn. Making Queer History. https://www.makingqueerhistory.com/articles/2019/12/16/holly-woodlawn

Dupêcher, N. (2019). Andy Warhol. The Museum of Modern Art; MoMA. https://www.moma.org/artists/6246-andy-warhol

Grimes, W. (2015, December 7). Holly Woodlawn, Transgender Star of 1970s Underground Films, Dies at 69. The New York Times. https://www.nytimes.com/2015/12/07/movies/holly-woodlawn-transgender-star-of-1970s-underground-films-dies-at-69.html

Hann, M. (2015, December 7). Lou Reed’s Walk on the Wild Side: what became of Candy, Little Joe and co? The Guardian. https://www.theguardian.com/music/shortcuts/2015/dec/07/holly-woodlawn-walk-on-the-wild-side-lou-reed-candy-little-joe

IMDb, & Sieger, R. (2015). Holly Woodlawn - Actress, Additional Crew. IMDb. https://www.imdb.com/name/nm0940341/bio/?ref_=nm_ov_bio_sm

Moyer, J. (2015, December 7). Holly Woodlawn: Actress and star of Andy Warhol’s Factory, immortalised in “Walk on the Wild Side” | The Independent. The Independent. https://www.independent.co.uk/news/obituaries/holly-woodlawn-actress-and-star-of-andy-warhol-s-factory-immortalised-in-walk-on-the-wild-side-a6763936.html

Patterson, J. (2007, September 26). “Oh, the things I did!” The Guardian; The Guardian. https://www.theguardian.com/artanddesign/2007/sep/26/art.theatre

Reed, L. (1972). Walk on the Wild Side [Song] On Transformer. RCA Victor.

Russell, G. R. (2025, February 5). “I’m a Woman, Darling”: The Life and Times of Warhol Superstar Holly Woodlawn. Interview Magazine. https://www.interviewmagazine.com/culture/the-life-and-times-of-warhol-superstar-holly-woodlawn

The Andy Warhol Museum. (2010). Andy Warhol’s Life. The Andy Warhol Museum; The Andy Warhol Museum. https://www.warhol.org/andy-warhols-life/

Trebay, G. (2013, November 1). The Real-Life Stories Told in “Walk on the Wild Side.” The New York Times. https://www.nytimes.com/2013/11/03/fashion/The-Real-Life-Stories-Told-by-Lou-Reed-in-Walk-on-the-Wild-Side.html

Villegas, J. (2021, July 8). Remembering Holly Woodlawn, Trans Icon and Puerto Rican Queen of Underground Cinema - Latina. Latina. https://latina.com/remembering-holly-woodlawn-trans-icon-and-puerto-rican-queen-of-underground-cinema/