For decades, Margaret Holloway performed Shakespeare on the corner of York Street in exchange for money. Behind the mythos of “The Shakespeare Lady” was a budding actress failed by a series of places and people—including at the Yale School of Drama.
If you walked past the steps of the Yale School of Drama between the 1980s and the early 2000s, you might have encountered a woman with wide, forceful eyes. She was thin, dressed in threadbare clothing, and often barefoot. She would offer recitations of Shakespeare in exchange for a few dollars.
Her performances were intimate and musical—she stretched her words out as if she were humming, until each sentence became a tune of its own. For her, theater was survival. It gave her an income and a means of expression. But she wasn’t always able to perform. She had paranoid schizophrenia, which came with debilitating hallucinations and bouts of aggression; sometimes, she would yell frighteningly at her sidewalk audience. To onlookers, she inhabited a gray space between reality and fiction. When did the performance stop and the person begin?
Her name was Margaret Holloway—perhaps better known as “The Shakespeare Lady.” She graduated from the Yale School of Drama in 1980. After graduation, she spent much of her life without stable housing, reciting Shakespeare to stay afloat.
For decades, observers have spun competing interpretations of Holloway’s life. One 2004 New York Times article identified her as a “street poet” with an “antic disposition.” An obituary, also published in The Times after her death in 2020, called her “a once-promising director and actor who struggled with mental illness and drug addiction.” Spike Lee featured her in his documentary series “New York Epicenters 9/11-2021½.” Multiple playwrights are turning her life into scripts, and Emmy Award-winning actress Uzo Aduba expressed an interest in developing Holloway’s story into a feature film.
Retellings of Holloway’s life have strung together sparse and often reductive pieces of information. Some stories portray her as the victim of a terrible mental illness, but others frame her as a proud woman who refused help, culpable for her own suffering.
This article is an attempt to tell Holloway’s story in its entirety, exploring the talent that propelled her to Yale, the people who isolated her, and the structures that failed her. Through thirteen interviews and dozens of documents tracing back to her childhood, this piece interrogates what is known and unknown about the life and artistry of Margaret Holloway—the woman who made York Street her stage.
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Margaret Holloway was born on September 7, 1951, to Walter Holloway, a preacher, and Bertha Holloway, a bus cleaner and homemaker. She was raised in Albany, a Black Belt county in Georgia. In 1961, when Holloway was 10 years old, Black local leaders, assisted by Martin Luther King Jr., began the first mass desegregation campaign of the civil rights movement. In 1964, Albany High School desegregated. Four years later, Holloway transferred there at the start of her junior year.
Most of her peers would remain in Albany for the rest of their lives. Those pursuing higher education would likely end up at the local junior college or state university. Not Holloway. In the spring of her junior year, she applied to A Better Chance (ABC), a program that placed high-performing students of color in prestigious boarding schools.
When Holloway arrived at ABC’s preparatory summer program in 1968, teachers remarked that she had “weak writing,” “below satisfactory” vocabulary, and “tremendous gaps” in mathematics. In a log of Holloway’s progress, a tutor initially noted her as “well-mannered but shy.”
As Holloway became more comfortable with her cohort, her teachers grew intrigued, if not charmed by her. “From Holloway’s writing, one gets a sense of explosion, spewing forth, release––as though she had never expressed herself out loud on paper before,” wrote one English teacher. The teacher described Holloway’s intuitions about literature as “unusually mature,” observing that students would defer to Holloway before contributing their own responses, as if she were their spokesman.
Though she was shrewd, she was not without humor. In Holloway’s progress log, a tutor recounts a story Holloway told about a white Albany High classmate who called her a slur and demanded answers to a math assignment: “Holloway gave her all the wrong answers and is enjoying the fact that the girl is still taking geometry.”
At the end of the ABC program, its director, Dr. Frank Morral, recommended Holloway to Northfield Mount Hermon, a boarding school in Massachusetts.
The Northfield Class of 1970 had 198 students. Faces from the yearbook suggest that nine of them were Black.
“I am the only Black student in my dorm and it can get quite depressing at times,” Holloway wrote in a letter to Morral. “It isn’t a very good feeling knowing my background when all I hear is talk about ski trips; $500.00 coats, (just for classes), vacations in London, etc.” One of Holloway’s few Black classmates, Cornell Hills, remembered a similar isolation. “You couldn’t be Black at Northfield Mount Hermon without hanging out with somebody [from the African American society] otherwise you would’ve gone insane. Like you were in hell with nobody to talk to.”
Even among other Black students, Holloway didn’t fit in completely. Hills remembers her as serious, intense, and even intimidating. “Back then if you wore an afro, you’re immediately identified as being somewhat militant,” Hills said.
Holloway had dark skin, and Hill remembers that she was perceived as the most “African” woman at Northfield. Hills remembers Holloway had few friends, and few romantic prospects. “She might have been seen as being too Black,” he said.
In varying degrees, Holloway lived on the outskirts of ABC, Northfield Mount Hermon, and the AFRO-AM Society.
Despite her alienation, Holloway found autonomy at Northfield. “A person does not have to live up to any reputation, there is almost no outside interference, and your parents cannot keep there [sic] apron strings choked around your neck,” she wrote in a letter to Morral.
After graduating from Northfield, Holloway attended Carleton College for a year as a comparative religion major. There, she acted in student productions for the first time and fell in love with theater. After her freshman year, Holloway transferred to Bennington College in southern Vermont, where she enrolled as a drama major.
***
It was at Bennington, a small, private liberal arts college, that Holloway’s best friend and dorm mate Laura Spector first heard the words “trust fund.”
Their friendship was not an obvious match. “Looking at us, you would never put two and two together,” Spector said. Spector, who is white, was a tiny dance major (“5’1 and a half,” she said, emphasizing the “half”). And there was Holloway: outspoken, “stunning, six feet, gorgeous” with long, slender limbs, piercing eyes, and an afro. Spector remembers her laugh well. Her shoulders would shrug, she’d let out big, whooping giggles, and her head would bob as she covered her mouth.
Spector and Holloway formed a friend group with two other students, including Philemona Williamson, now a prolific visual artist. “It was a family, the best family I ever had,” Spector reminisced. “I think for Margaret, too, it was like a really bonded family.”
At Bennington, privilege was assumed, not displayed. Students were artists: they lived in the woods with personal studios. Ski coats were replaced with big overalls and flowing skirts. When commitment to high art was the standard, students were regarded more for their talent than their family history. And Holloway had talent in spades.
The qualities that had isolated Holloway—her charisma, her physical presence, her wit, her laughter—bonded her to her new cohort. According to three classmates, Holloway was a Bennington star. “They viewed her with absolute respect. Absolute awe. She was a queen,” Spector said.
Every year, Bennington students took a non-resident term to pursue their art in the “real world,” which often brought them to a second bubble: New York City. But Holloway, who lacked the same familial wealth as her peers, remained at Bennington.
In fact, Holloway was estranged from her parents entirely. Of the thirteen people I spoke to—close friends, artistic collaborators, acquaintances who knew her only as the Shakespeare Lady—all mentioned that she talked openly about parental abuse. Some recounted sharp tensions with her father, and many remember Holloway saying she had been abused by her mother.
At Bennington, Holloway had confided to Spector that a family member had raped her as a child. She was abused. She wanted no contact. To Spector’s knowledge, Holloway never returned to Albany after she left for Northfield. Holloway stayed at Bennington during holidays; for Thanksgiving one year, she went to Spector’s house. During the summers, she took on odd jobs at Northfield School, ABC, and Bennington.
Bennington was her family. The institutions that brought her to the North were her home. It was her Southern upbringing, however, that informed her first original play.
On a sparsely decorated stage, Holloway stood alone, improvising much of the material and in total control. Holloway became Jeanette, a Black servant to a Southern white woman. Jeanette lamented the death of her first lover, who was lynched after “looking wrong” at a white woman. Jeanette gossipped with her friends. She went to large parties. She attended a Southern Baptist church service.
Repeatedly, Jeanette’s thoughts flash back to an early childhood memory when her mother, bathing her, told her what to expect from her life. In a parallel vignette, a Haitian voodoo dancer and drummer cast bones that prophesied the events of Jeanette’s life.
“The real strength of the play is that Ms. Holloway does most of it by herself,” read a review in the Bennington Banner. “She could just decide: this is it,” Alex Brown, a Bennington classmate, told me. “They’re listening. I’m ahead of them. Most actors are waiting to see if the audience is there.”
It’s hard not to read Holloway’s life into the play. Her life, like Jeanette’s, bore the weight of circumstance––of poverty, of injustice, of life as a poor Black woman in the South. Circumstance, and the limitations it imposed, became a kind of predestination for Jeanette, committing her to a life of poverty and discrimination.
Not so for Holloway. No bones could have foretold that she would become a standout in one of the country’s most elite drama schools––nor could they have foretold what happened afterward.
***
In December 2004, the New York Times published an article about Holloway. It was headlined “A Resurgent Downtown Wearies of a Street Poet’s Antic Disposition.”
“Margaret Holloway chose Shakespeare [Hamlet, Act I, Scene II], of course, for her first performance after serving 53 days in jail for failing to appear in court on charges of disorderly conduct, breaching the peace and other urban theatrics,” wrote reporter William Yardley.
In the article, Yardley quotes a bartender at a local pub. “She just badgers you,” the bartender says. “My buddy paid her $50 once to be left alone for a year.”
According to the Times article, Holloway was set to appear in court to discuss her use of crack cocaine and schizophrenia medication. “But perhaps most important,” the article read, “she must convince the judge that she has stopped offending merchants and passers-by on the gentrifying blocks east of the historic New Haven town green, where expensive new condominiums are on sale just steps from her squalid third-floor room.”
In the public consciousness, Holloway had all but lost her name. To most, she was “The Shakespeare Lady”—a figure bearing the mythology that she was once a student at Yale. Yet, little is known about what happened when Holloway attended the School of Drama. When Holloway’s career was finally within grasp, circumstance plummeted her life in the opposite direction.
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When describing the culture at the Yale School of Drama, Dennie Gordon, Holloway’s classmate and one of the School’s first female directing students, repeatedly used the phrase “psychological torture.”
“It was like an Agatha Christie novel,” Gordon said. The directing students were immediately made aware that only some from their original class would make it through the School of Drama. “You look at your colleagues and go, ‘who’s gonna die?’”
When Holloway was a student, the School of Drama operated on a probationary basis. For their first two years, no student’s spot was secure. Each year, faculty expelled students who did not perform up to par.
Such was the philosophy of Dean Robert Brustein, founder of the renowned Yale Repertory Theatre. Brustein—who passed away in 2020—was a bold, relentlessly authoritative giant in the American theater scene.
Brustein came to Yale with a pedagogical vision of “professionalizing” the school. Students Brustein championed would get the opportunity to work with his professional actors at the Yale Repertory Theatre.
It seemed to Gordon that the pressures of the School of Drama only strengthened Holloway’s dedication to her training. Gordon remembered her as “intense,” “fearless,” and “regal”—impressively in command of her material. “I think a lot of people in my class were afraid of her. I was a little afraid of her too.”
Brustein had “a few woman favorites,” Gordon told me. Holloway was not one of them. Gordon remembered how Brustein often overlooked Holloway, reserving recognition and opportunity for his favorite students—one of whom was Meryl Streep. “I would say Holloway was equally a star in the making but had to fight harder for everything she got,” Gordon said.
Brustein had controversial opinions about race: he publicly criticized August Wilson, a Black playwright who advocated for theater about the Black experience, accusing Wilson of promoting separatism.
In 1972, a group of eight black School of Drama students staged a protest in front of the Yale Repertory Theatre, holding signs that read “We Do Exist” and “King Brustein is insensitive to black artists.” According to Yale Daily News coverage, the protestors expressed frustration over “stereotypical casting of blacks as marginal characters, and hostile attitudes expressed by the faculty at attempts to present elements of the black experience.”
Brustein chose not to comment for the YDN article. In many ways, the structure of the School of Drama spoke for itself.
“This is the way he operates, on students’ fear of losing their Yale degree,” said one student in a 1975 YDN article. “He confuses loyalty with competence,” the student continued. “His attitude is, ‘If you don’t like it, get out. And if you’ve come this far, what can you do?’”
In the spring of 1975, Robert Lewis, the head of the acting department, cast Holloway in a class production of “Death Comes to Us All, Mary Agnes” by Christopher Durang, a School of Drama alum and Brustein favorite. Lewis cast Holloway as the maid, a sexual role that required Holloway to take off her shirt and seduce two male characters. Later in life, Holloway said she felt she was cast as the maid because of her race.
On March 27, 1975, Brustein received a letter from Holloway. In it, Holloway described how she had approached Lewis with concerns about the “physical nature” of the play, but he had dismissed her. That night, at rehearsal, Holloway says Lewis mocked her in front of other cast members by implying that she was too fragile to even hear sexually explicit language. “Although I didn’t show it, I was absolutely shattered,” Holloway wrote. “I could not believe that a man I had loved and respected and hung on to his every word for all these months had repeatedly insulted my personhood that way.”
Holloway concluded the letter by expressing that she had “no place to turn.” “I considered begging out of the part, but after Bobby’s response I feared my acting classes would be in jeopardy,” she wrote. “I could not afford that. I cannot express to you the loss I feel.”
On the official Yale School of Drama program, Dennie Gordon plays “Elizabeth,” the maid. In the published play, her name is “Margaret.”
Holloway had enough.
That same year, Holloway left Yale and went back to a happier time in her life— Bennington—where she pursued a master’s in theater. There, Holloway wrote and directed “Facials,” her thesis play. According to a review in the Bennington alumni magazine, the play examines the life of two women—a prostitute and a journalist—as they “wrestle with authority figures and sexual domination.” “My image was that both women were wallowing in shit,” Holloway said.
The majority of the 35-person cast were non-drama majors. “I loved working with people who were new to the theatre who didn’t walk on stage to prove the same point they always had,” Holloway told former classmate Brown, now a reporter for the Bennington alumni magazine.
Back at Yale, in 1978, Yale President Bart Giamatti did not renew Brustein’s contract. The next year, Lloyd Richards took over the School of Drama as its first Black Dean.
Holloway returned to the Yale School of Drama in 1979, this time as a directing student.
***
ANNE
My faith’s weak, Father.
ABBOT
It will come, child, Never fear.
ANNE
I don’t think so. I feel something else has come. I hear voices. I don’t think the voices were holy ones.
When she returned to the School of Drama in 1978, Holloway chose the unpublished play, “God’s Smoke” as her thesis production. The play, written by Bennington professor John Gardner, is relentlessly dark: set in the 14th century, it follows an abbott, a monk, a countess, and her kidnapper menaced by plague and hallucinating the presence of Death personified. That plague, Holloway comments in her final essay, parallels modern-day “disease and mental illness and violence” which are “at plague proportions.”
Through the play, Holloway sought to showcase what she termed the “theater of hunger.” “We all have hungers,” Holloway wrote in her final essay: hungers for food, shelter, sex, reproduction, freedom, understanding, and distinction. Narcissism, too. However, she continues, “obstacle” forces, which range from natural catastrophes and birth defects to societal prejudices, tyranny, and repression, impede satiation. The conflict between our hungers and these obstacle forces is the subject of Holloway’s theater.
Holloway placed her theater of hunger in opposition to “intellectual theatrics.” “In order to abstract the truth,” Holloway writes, “the artists must first know the truth.”
To know the plague, you must also experience the plague.
In playwright and classmate Allan Havis’ memory, Holloway’s mental health started to deteriorate during her last semester at the School of Drama. Until this point, none of her friends I talked to, at Bennington or at Yale, had noticed signs of mental illness. Havis remembers Holloway’s intensifying substance use and emerging schizophrenia.
Havis also noticed that Holloway would experience “cycles of paranoia.” She felt that faculty members paid little attention to her, and that “she was not going to get the benefit of the so-called Yale mafia.” It certainly didn’t help that she felt Lloyd Richards was ignoring her. According to Havis, when Holloway re-enrolled at the School of Drama, she felt heartened that she had a Black dean, and she expected Richards to understand her and support her career. As Holloway approached graduation, her paranoia became more frequent, and she would have frightening moments of anger. It was unclear exactly what was happening to Holloway, but it was then that Holloway’s classmates could tell something was changing.
“Many artists of past and present have aspired to some notion of a theater of hunger,” Holloway wrote in the final paragraph of her thesis. “Many were imprisoned, ostracized, driven insane, etc.” Nevertheless, she wrote, “these artists know that there is no separation between the quest toward a theater of hunger and a quest toward a way of life.”
“We continue in this quest.”
***
Among Holloway’s close friends, how she ended up on the streets remained a mystery. One man, though, had a sense of how it happened. In the two years post-graduation, Richards received numerous accounts of Holloway’s increasingly erratic behavior.
In August of 1981, Holloway, then a Yale graduate, sent Richards a letter regarding her interest in teaching at the Yale School of Drama or Repertory Theatre.
Holloway had tried to launch her career. She worked with Brustein as an assistant director for a production at the American Repertory Theatre, followed by a short post at The Everyman Street Theater in Washington, DC. Yet Holloway ended up back in New Haven, hosting acting workshops for high school students. Richards did not hire her.
Nine months later, Richards received word of Holloway again; this time from a librarian at the School of Drama. Holloway had stolen a book. Holloway’s behavior had become “markedly irrational,” the librarian wrote. In one instance, the librarian said Holloway scribbled nonsense on a piece of paper and pinned it to a bulletin board.
A day later, Richards received a second notice. The librarian had threatened to call Campus Police on Holloway. She recounted that Holloway had left the building shouting, “Racism strikes again!”
In Bennington classmate Richard Dailey’s documentary about her, Holloway recounts being evicted from her apartment in 1983.
Through her next two decades as the Shakespeare Lady, a legion of passersby formed a community around Holloway. They were struck by her recitations, struck by her conversational wit, struck by the fact that, after a brief encounter, she would remember their names for years afterward. This circle included multiple journalists, a rabbi, local musicians, and a lawyer who represented her pro bono.
“Her moments of lucidity were just astonishing,” Dailey told me. “You could understand the vestiges of her genius that would come flashing out.”
When Dailey asked her to recite, she’d go quiet before beginning. Something deep inside her would seem to shift. It was as if the words were committed to memory––committed to soul. She’d cut off some words quickly, but she’d hold others until her voice broke. It was rhythmic, hypnotic, declamatory. She did it all in a perfect General American accent.
Holloway’s classmates don’t remember her having an interest in Shakespeare. Holloway’s street repertoire was a product of her theater education. She recited lines from “Medea,” “Canterbury Tales,” “The Tempest,” “Hamlet,” and “Macbeth”—all plays she acted in or directed. In one video posted of her act, she recites an excerpt from “God’s Smoke.”
“I always took the idea that she was probably the most famous performer in New Haven,” Chris Arnott, Holloway’s friend and writer for the Hartford Courant, told me.
Holloway’s story as the Shakespeare Lady, then, was ripe for interpretation.
“She was her own Greek tragedy,” Gordon said. “It’s so poignant that she held onto the drama school and the Yale neighborhood, remembering that her best times were there when she was her best self.”
Cecelia Rubino, a classmate who acted in Holloway’s School of Drama thesis, later included Margaret as a character in her documentary, Remembering Shakespeare. Rubino is less concerned with the spin of the narrative, but the urge to turn Holloway’s life into narrative in the first place.
“I’m just like, how could you film her?” said Rubino, “But I had the same thing of like, why am I?”
***
In 2005, Spector, Holloway’s best friend from Bennington, made a trip to New Haven. She hadn’t seen Holloway since the 1980s, when Holloway had asked her for drug money. By now, Holloway had stopped her recitations on York Street and moved into state-assisted housing. She seemed healthier—less frail than she had been in the days when she was addicted to crack cocaine.
In her apartment, “time stood still. It was just like a dorm room,” Spector told me. “She had Michael Jackson, and she had Motown and all that.” When Spector and Holloway ventured out to get food, Spector remembers Holloway becoming “paranoid” and “internally small,” shrinking back as people looked at her.
In her years post-Shakespeare Lady, then cloistered in her apartment, Holloway had a regular visitor: Joan Channick, the warm but matter-of-fact chair of the Theater Management program at Yale School of Drama.
Channick gave Holloway her number a few years prior but grew overwhelmed by the number of calls she was getting from Holloway. Holloway would ask Channick to bring her things or give her money. Mostly, though, she just wanted to talk about theater. Holloway would tell Channick stories about praise she received from Brustein and productions she directed. “I heard all of her stories over and over and over again,” Channick remembers. “And to be honest, I didn’t know what to believe.”
In the last two years of her life, Holloway moved to a nursing home. Every month Channick would visit. Every time, Holloway prepared written lists of things she wanted to talk about.
When the pandemic hit, Channick and Holloway regularly called each other.
Then, Holloway stopped responding. After two weeks and no response, Channick began a lengthy back-and-forth with Holloway’s conservator; because they weren’t family, neither Channick nor any of Holloway’s other friends could know the status of her health.
On May 30, 2020, at the age of 68, Holloway died of COVID-19. Nobody but Channick and Holloway’s family members knew until news outlets published her obituary.
***
To Channick, Holloway reminds us of the “precariousness of anyone’s life.”
But Holloway’s life had been precarious from the moment she left Albany. Theater gave Holloway a means of interpreting her experiences; but elite institutions were interested in her talent, not her personhood. When Margaret arrived on the East Coast, she carried with her a childhood wrought with trauma. At every school she attended, some aspect of her identity—her race, her class––isolated her.
As artists, friends, and family tell Holloway’s story, they decide how she should be remembered. Holloway becomes a caricature of the mad artist. Or an inspirational story of an unbreakable commitment to art—the embodiment of her own theater of hunger. Or she’s just the Shakespeare Lady: mentally and physically ill, reciting nonsense outside of the School of Drama. This article, too, tells Holloway’s life through dozens of perspectives, but not her own. Holloway, like all of us, is a kaleidoscope of stories; she just doesn’t get to tell any of them.
– Chloe Budakian is a sophomore in Silliman and an Associate Editor of The New Journal.
Images courtesy of Chloe Budakian.
