An adaptation of The Pillowman, from Ruth on the Rocks director Ricardo Gamboa is drawing crowds to Humboldt Park’s AfriCaribe Cultural Center. Led by Englewood-raised actors Omari Ferrell and Tyran Freeman, Gamboa’s take on the modern classic replaces the play’s dystopian setting with Chicago, offering unique parallels between the script’s treatment of police brutality and the city’s own history of state violence.
Written by British-Irish playwright Martin McDonagh, The Pillowman takes place in a totalitarian police state in which two brothers, the writer Katurian (played by Ferrell) and his brother Michal (Freeman), are tortured for their alleged connections to a series of disturbing child murders. The story is told in part through glimpses of Katurian’s short stories that bear an eerie similarity to the killings plaguing the town. Since its premiere in 2003 at London’s Royal National Theatre, the play has received critical acclaim for its complex depiction of the choices we are forced to make under the threat of fascism. Gamboa’s production features a cast that is entirely Black and Latino—a change from most productions of The Pillowman, which typically cast white actors for the play’s lead roles, Gamboa said.
Gamboa first developed the idea to stage The Pillowman after interviewing brothers Sean Tyler and Reginald Henderson on Gamboa’s talk show The Hoodoisie. Tyler and Henderson were wrongfully incarcerated for twenty-five years after surviving torture at the hands of Chicago police as teenagers.
“What happened to Sean and Reggie is not an aberration in Chicago police history. It’s actually the norm,” said Gamboa, who after hearing the brothers’ story was reminded of The Pillowman. Over 120 people, predominantly Black men, were tortured by members of the Chicago Police Department from 1972–1991 under then-CPD commander Jon Burge. Gamboa’s play falls on the ten-year anniversary of the passing of Chicago’s 2015 Reparations Ordinance, meant to provide financial redress and counseling, among other services, to survivors of Chicago police torture. Notably, the ordinance also promises to create a memorial for survivors of police torture, which has yet to be built.
Gamboa wanted to engage with Chicago’s history and present of police violence through their staging of The Pillowman, which they describe as less of a reimagining and more of a “revitalization.” Gamboa made no edits to the script itself; instead, many of the updated elements come from directing choices, most visibly the set design and costuming, executed in partnership with collaborator Sol Cabrini de la Ciudad. Katurian’s character, who in other productions of the play often dresses in a preppy look with a collared shirt and slacks, instead wears a hoodie and Champion sweats.
“I think racially re-coding the play, a play that’s written by a white playwright…what I think actually happens is we don’t have to do much to it. Casting two young Black men from the South Side of Chicago, saying those words in their tongue and their tone automatically changes it,” Gamboa said.
The show’s leads, Ferrell and Freeman, don’t just play brothers on stage; they’re practically brothers in real life. The duo has been friends since the fourth grade and met Gamboa while just entering high school. Both Ferrell and Freeman participated in Gamboa’s youth theatre program Commercial Free at Pilsen’s National Museum of Mexican Art.
“I don’t think there could be two other people to do this play in my mind,” said Gamboa. “I’m just so proud of how talented they are. Seeing them be the artists that I feel at least that they were meant to be is amazing.”
Years after Gamboa met Freeman and Ferrell, the actors are all grown up. On top of working full time, they are also fathers to young children. Gamboa has been particularly accommodating of his busy schedule, which is not common in the wider Chicago theater scene, Ferrell said. This isn’t just kindness, although it is kind—it’s also Gamboa’s way of making space in an industry that usually favors classically trained actors with more time and resources. Gamboa wants the stories they tell to reflect Chicagoans’ lived realities, and that starts first and foremost with the ways they create theater.
Acting, said Freeman and Ferrell, is also a way for them to release the stress from their daily lives, even as the play’s themes of police violence are also a stark reminder of their lives beyond the stage.
“I think, as a Black man, it’s sometimes the duty of us to kind of check our emotions before they become too visible. This play allows me a space to not do that, to just allow whatever emotions I have be the emotions that I have, and bring them to the character,” said Ferrell.
“This is really my outlet,” said Freeman. “All of the pent-up stress, all of the pent-up anger, the self-hate, the self-doubt: I let it flow through the character. In that way, [the performance] is honest. At the end of it, I don’t feel weighed down or drained because of how emotional the play is. I feel much better, actually. I feel lighter at the end of it.”
Ferrell and Freeman were first introduced to The Pillowman at a reading Gamboa hosted in September 2023 that included actors from their recent play The Wizards. While many of Gamboa’s collaborators at the reading liked the play itself, they also expressed concerns about whether the world needed a staging of a play that centers on heavy themes like child abuse and police violence.
“A few weeks later, October 7 happened with the al-Aqsa Flood operation. And then October 8, Israel began its genocide. All of a sudden, this idea of, we have to shield the violence that happens against children—even though in the U.S., we had been seeing it happen to Black kids, to brown kids, by police or school shootings—was thrown in our faces, and we were intimate with it, with the genocide of Palestinians,” Gamboa said.
Gamboa’s version of The Pillowman incorporates projected short films meant to mimic the ways in which violence against children is communicated to the wider world through screens: our televisions, phones, and laptops. Gamboa also began thinking about the sort of media we give to children. The play’s eponymous Pillowman figure is reimagined in Gamboa’s production as a large puppet, made in collaboration with Chicago-based puppeteers Chio Cabrera and Agnotti Cowie.
These aspects of the play’s production interact with and reflect the rising tide of fascism nationally and internationally, from the U.S.-backed genocide of Palestinians, to ongoing ICE immigration raids and the recent alleged extralegal kidnapping of Mahmoud Khalil. However, Gamboa isn’t interested in offering the play’s audience a neat way to feel about these global events. Instead they hope The Pillowman provides a route for the audience to feel their way toward their own conclusions.
“We always think that theater trades in representation, right? Like, ‘Oh, I’m gonna show you this thing that I’m trying to say.’ But really, theater, like all art forms, should be trading in sensation, and what are the feelings that they produce, and what is the kind of emotional impact of [the] work. What does it emotionally inspire?” they said.
“This play, we hope it brings people to realization, it brings them to commiseration, and it works to start motivating conversation and action.”
The Pillowman, AfriCaribe Cultural Center, 2547 W. Division St. March 7 through April 12. Fridays and Saturdays, 7pm. Tickets are priced by sliding scale donation, starting at $10. tickettailor.com/events/thepillowman/1549791. The Pillowman was produced under Concrete Content, Ricardo Gamboa’s theater production company that brings radical aesthetics and politics to Chicago’s theater scene. Gamboa recently wrapped an approximately fifteen-week sold-out run of their production Ruth on the Rocks, which premiered as part of the seventh annual Destinos, a citywide theater festival dedicated to raising the local, national, and international profile of Chicago’s Latino theater scene.
Charlie Kolodziej is a freelance journalist whose work has appeared in South Side Weekly, Chicago Reader, and the New York Times.