This wasn’t always a trilogy. About a decade ago, the Chicago-born playwright Joshua Allen crafted two stories, The Last Pair of Earlies and The October Storm, each in different time periods but set within the same three-flat apartment building on Chicago’s South Side. Earlier this month, Allen added a new chapter to the building’s storybook—a final visit to round out the trio of play that are now called the Grand Boulevard Trilogy. After years of building a steady television career, with shows like Empire and The Morning Show earning him writing and co-executive producing credits, The Prodigal Daughter (through June 22 at Raven Theatre) shows a writer much changed from the Allen who started the series years ago.

“I like to tell people my trilogy is like having two teenagers and a newborn, because I hadn’t written a new play in a very, very long time,” said Allen, who still has family on the South Side. “It’s not quite like riding a bicycle. You can kind of forget, especially when you spent over a decade writing television.”

Though it didn’t premiere until 2021, Allen originally wrote the first in the series, The Last Pair of Earlies, while in graduate school at Juilliard in the late 2000s. Back back in 2009, he recalled, there was a different pandemic going around: H1N1. Feverish and bedridden, he “just started weirdly time-traveling in my head.” The resulting play operates on two tracks: In 1921, the Earlies are young lovers dreaming of a brighter future by moving from Mississippi to Chicago where the “only color that matters is green,” and in 1938, the Earlies are living in an apartment on the South Side of Chicago, where the wife, Della Rose, dreams of a chance for the two of them to move home, a dream not shared by her husband.

“I wondered what it would be like if people could talk to their younger selves,” Allen said of the play, “and I wondered what it could be like if people found themselves 18 years later with unrealized dreams, and what that does to people.”

Allen said he also wanted to represent his family, which has roots in the South and whose members made a similar journey as the Earlies during the Great Migration that saw something around six million Black people move from the South to Northern, Midwestern, and Western states starting in the 1910s. Two years after writing about the Earlies, during a residency in Poughkeepsie, N.Y., Allen decided to dive deeper into the life of one character mentioned as a passing reference in Earlies: Mrs. Elkins, the apartment building’s landlady.

“I thought to myself, ‘Oh, what’s that about? Why did I mention the landlady? What’s her life like living down in the basement?’” Allen recalled.

Thus The October Storm, which debuted in 2023, a decade after its writing. Set in 1960, October Storm takes us into the basement apartment of said landlady and her 16-year-old granddaughter, Gloria, whose mother is off pursuing a Hollywood career. There’s already a generational divide at play between the old-school disciplinarian and the teen who longs for freedom. When Louis, a military veteran, moves into the building, he may liberate them both, or drive them even further apart.

Both plays, Allen said, had been written by around 2012. With positive feedback flowing in from the Earlies premiere and an early staged reading of October Storm, Allen said Raven approached him about what might be next for his series of stories, eventually leading them to commission the latest and final installment, The Prodigal Daughter. This one flashes back to the Red Summer of 1919, when riots—sparked by white folks aggrieved by post-WWI competition for jobs with Black Americans, who fought back—broke out across the country. Allen hones in on the story of Virginia Bass, a successful saleswoman who decides to pay a rare visit to her estranged father and the rest of her family in Chicago, unearthing secrets that have been buried for years.

While the series may have started out as time-traveling daydreams, Allen noted that he was very intentional about when each play was set. In The Last Pair of Earlies, the 1939 setting is a nod to his grandmother’s birth year, and October Storm’s 1960 a nod to his mother. Rather than bring The Prodigal Daughter to the present or incorporating in his own birth year, he decided to keep following his matriarchal lineage back to around when his great grandmother was both.

Last week, I had the chance to chat with Allen and revisit his Grand Boulevard Trilogy as his Chicago-based triptych is set to conclude. The following has been edited for length and clarity.

JERALD RAYMOND PIERCE: What were you able to learn from those first couple plays that you were able to incorporate into this newest one? I’m also curious how your television experience may have played into your writing.

JOSHUA ALLEN: It was hard because, if it’s a trilogy, it wants to feel stylistically of a piece. At Juilliard, Marsha Norman used to always say you get two years, because you’re a different person every two years. I was like, Oh, but it’s been like 12, so am I the same writer? Is The Prodigal Daughter going to stick out like some sort of a sore thumb? I was worried about that, but I just had to put it out of my head. 

As far as television goes, most of the shows I’ve worked on, you can’t write a scene longer than three pages. So I sat down to write The Prodigal Daughter, and I was like, Okay, so they’re done. Then I was like: Oh no, they can’t be done. This has to be a 15-page scene. So I set that challenge for myself. It’s about an 80-minute show, and there are only five scenes, and so I just wanted to get back into letting conversations and moments breathe. There are no commercials, no car chases, no Game of Thrones dragons. There’s really nowhere to go, so you have to make sure you’re setting the table for an 80-minute pressure cooker, because that’s what I hope the play is.

A big aspect of the feeling of a pressure cooker is the outside world that we don’t get to see. This taking place—

I hate the term race riot, but that’s what everyone calls it. I consider that event the seventh character in the play.

Did you start from there? Or was that environment something you found as you were crafting the story inside the house?

I did want to start from there because, about a year or two ago, when Raven commissioned me, I was thinking about the protests that erupted nationwide around George Floyd, Breonna Taylor, and I was like, Oh, we are still doing that. We’re still not valuing Black life. I knew it had to be a Chicago story. So when I was thinking about that, I was like: Oh, I do know about Red Summer, and I do know the story of how that erupted in the summer of 1919 in Chicago and lasted for days.

I also knew I wanted to write a play about somebody who comes home thinking one thing, but then another thing happens. Virginia’s hands are not totally clean: She came home to kind of show off, but what she was not expecting was all hell to break loose. One of the challenges in the production was figuring out with the designers and director and actors how to keep the threat of danger alive on the outside, but not so much that people only care about that and we can’t scratch the surface of the real emotional stuff going on between them.

What was your research process like for these plays? You mentioned that your family came up to Chicago during the Great Migration. Were you mostly drawing on your own background and that of the folks around you?

I did a lot of external research. I’m a fourth-generation Chicagoan, so there was really no one I could sit down with and interview about it. I have family from Louisville, Tennessee, Northern Alabama, and Mississippi. So I did a lot of external research.

Then there were things that I just realized I knew, like in The October Storm when Mrs. Elkins brings Louis, the new tenant, into the building. She goes, “The rent is $50 a month.” I didn’t look that up, and I had a woman come up to me and go, “How did you know that? In 1960, the first apartment my parents rented was $50 a month.” I was like, “That’s the ancestors. I don’t know. I don’t know, ma’am.” I didn’t look that up. I just made it up. I should have probably done some sort of inflation calculator, but I was like, I’m too busy worrying about the play, so I’m just going to make it up. I’m just going to make something up. It turns out that was accurate.

There’s this sense of this trilogy overall being both contained, because it’s all within the same building, and expansive, because it spans decades. What led to the choice to have all of these stories take place in the same building versus, say, hopping around the South Side or different Chicago locations?

I think because I was covering so many different time periods, I didn’t want to also cover so many spaces. I wanted to explore staying in one place but moving around in time. I considered doing both, but it felt a little too herky-jerky, if that makes sense.

It feels like, at least in my point of view, that the combination of the three gives a really solid sense of place.

If I had written a fourth play in that apartment building in 2024, it’d be set in a Soul Cycle. It would be in a Whole Foods, or whatever they did to it at that point.

Maybe that’s the next iteration.

Maybe, it’ll be a workplace comedy in a Whole Foods.

What was the biggest surprise or discovery you made during the creation of these plays? Was there something that came up in your writing process or your research process that you were surprised by or inspired by?

Yes. There are things that look intentional that were not. Like, in all three plays, everybody’s like, “Whoo, it’s hot out there.” In The Last Pair of Earlies, it’s a heat wave in April, and in The October Storm, they’re in the basement apartment, so the furnace is hot. Then it’s summertime in the Prodigal Daughter. I don’t know thematically what that was doing, because that was not intentional, but as I looked at all three plays, I was like, “Oh, everybody’s complaining about the heat. What’s that about?”

Honestly, it feels like it kind of goes back to that idea of the pressure cooker we were talking about—this idea that there’s always a sense of heat behind all these people’s lives, a little pressure that way. That’s interesting.

Yeah, I think people don’t think of Chicago as a peaceful place. Its reputation for centuries has been not peaceful. But just the idea that there’s always a sort of low-grade menace if you are an African American person in this country—there’s just always that. But you can’t let that take over your life, because you mad at your daddy so that’s what we doing today. Like: I’ll worry about racial violence later, but right now I have issues with you.

I have to ask, since you’re somebody who is from the South Side of Chicago, it’s interesting to me that all three of these plays premiered at Raven, which is a far North Side theatre— 

My family made a pilgrimage basically in a covered wagon to come see it.

Are there plans to stage these somewhere on the South Side?

I don’t think so. There are no plans that I know of.

How has your family reacted to the plays?

I will tell you a story about The October Storm since you didn’t get to be there. My aunt, my father’s sister, came to see the show; she sat in the front row. And there’s a moment where Mrs. Elkins and Louis, the troubled war vet who becomes her tenant, they kiss. But it’s accidental. Oh my God, did I do that? Landlady’s can’t be kissing their tenant. When Mrs. Elkins backed away and was like, “I’m sorry, I didn’t mean to do that,” my aunt yells, “No girl, go back and get you some mo’!”

I was like, “Oh, yeah, so they can hear you when you do that.” At intermission I was like, “You can’t do that.” She was like, “I just wanted to encourage her.” I was like, “It’s going to happen anyway, because they’re going to do what I wrote. This is not choose your own adventure. You don’t get to encourage her and then she makes a different decision.”

So all that is to say they were very engaged as audience members.

That makes me curious about your point of view on the kind of audience behavior conversations that have been happening in theatre—the idea that you should be able to bring yourself to the theatre, engaging in whatever way you feel comfortable. How are you seeing that kind of conversation?

Well, I have complicated feelings about that. I had to say that to my aunt because she doesn’t go to theatre. But there is a sort of scolding “behave” that I’m not sure gets enforced equally. Like, Lauren Boebert, you know better when you’re at that musical and you doing what you’re doing. But my grandmother opens a Werther’s Original and she’s scolded? Come on.

I do feel like the link between theatre and religion goes back to the ancient Greeks. So there is a sort of church-like quality to it at certain points, and you could feel like it’s call and response. I was just like, Auntie, can your response be a little less aggressive?

If there’s any moment in any of the three plays that you feel like encapsulates the full trilogy for you—a moment that says “Grand Boulevard Trilogy” to you?

I think it might be a moment in The Last Pair of Earlies, after Della and Wayland have their knockdown-drag-out and it’s clear that she’s got to figure something else out with her life. Her best friend, who she also had a little bit of a falling out with, comes in and brushes her hair and Della says something to the effect of, “I want to go home. I want to lay in tall grass with no noise except the breeze in the leaves.” I think that encapsulates it, because at its heart, this whole trilogy is about people uprooting their lives in one direction or another.

We always hear about the Great Migration as everybody just trying not to get lynched, which is largely true. But her decision to actually go back to Mississippi represents a decision about what she values, and she is now very clear that she and her husband have different values and it’s just not going to work. Just the boldness of that—it is courageous to uproot your life. It is courageous to go in either direction, North or South, not knowing what’s waiting for you there.

Jerald Raymond Pierce (he/him) is the Chicago editor for American Theatre. jpierce@tcg.org