In Conversation With Cheyenne Barboza
Wednesday February 18 2026
In Conversation With Director of August Wilson's Gem of the Ocean, Cheyenne Barboza
Jacob: Cheyenne, welcome to our interview about your production of August Wilson's masterpiece, Gem of the Ocean. How are you feeling today? Human to human.
Cheyenne: I feel the veil between our world and the ancestral world is thin. I'm feeling that closeness. I’m feeling it in the passing of loved ones. I’m feeling it in the arrival of new life. I’m feeling it in the somber aftermath of the holidays and photo albums of times gone by. That’s what I’m feeling right now. Truly.
Jacob: I love it. And where are you? Tell us where you are and what you're doing there.
Cheyenne: I am the program and production manager at Painted Bride Art Center in Philadelphia. I am currently in Philly, and I split my time between Philly and New Haven.
Jacob: And you have deep roots in Philly, right? You completed your undergraduate work there and have been supported as both an artist and, specifically, as a director by several Philadelphia-based theatre companies. Would you share a bit more about your connection to the Philly theatre scene?
Cheyenne: Sure. I definitely got my start in Philadelphia. We have some incredible theatre companies here, Arden Theatre, Wilma Theater, and Philadelphia Theatre Company, which was the first to employ me as an assistant director way back when. I worked with Theatre in the X and a whole host of smaller theatre companies. The Painted Bride is, of course, where I eventually got a full-time position way back in 2014, and I’m happy to be back around as they start this new iteration. They are also a sixty-year institution that has gone itinerant after having a brick-and-mortar for so long, and they have a devoted following of artists and community folks that galvanize around this institution. So, it's been an incredible ride with Philly.
Jacob: And you are a Connecticut baby, yes? You were born and raised in Connecticut.
Cheyenne: Waterbury.
Jacob: Tell us more about that history in terms of where you grew up and your community here in Connecticut. Was it the University of the Arts that made the connection to Philly, or was there something else?
Cheyenne: I was born and raised in Waterbury, Connecticut. My mother would say, my whole family would say, really, that I came out born for the stage. My earliest memory of being in a show was being cast in a local high school's production of Oliver Twist. They were casting kids for the orphans, and I just thought I made it big. I can still sing those songs in my head from then. Then, when I was in middle school, they announced that they were going to build a performing arts magnet high school downtown. I claimed it every day. I would say, “Look, Mom, you know, they started construction on my school. Look, Mom, it has beams. Look, Mom, it has windows.” We drove by it every day to go to her job, and when the lottery finally came out, I got in. I was in 8th grade when I got there, and you could only take playwriting in high school, so I wrote a letter to the playwriting teacher, and I said, “I need to. I write plays. I want to write,” and I got special permission to join the high school course for playwriting with Bruce Post, who is a published playwright with roots in Connecticut. He's since retired and lives down south, but he was my mentor. I knew I was going to go to school for playwriting. I knew I was going to be a professional theatre artist. I consumed everything I could. I went to the Center for Creative Youth at Wesleyan University when I was in high school. Then I found the undergrad playwriting programs that met my needs. The University of the Arts was one of them because most of the programs are general theatre programs, and then you go get your MFA in Playwriting. The list was much smaller when it came to undergraduate playwriting degrees. I could do that at Drexel, and I could do it at UArts, so I did a weekend trip with my family, we visited both schools, I applied to both schools, and UArts was the one for me.
Jacob: The thing that I also marvel at is the way in which you've really rooted yourself to this community here in Connecticut, and you've also maintained your connections to the Philly theatre community. It feels like there's a real bridge between your life here in New Haven and your life there. When did the directing bug hit you? I remember the moment when someone told me, “You're a producer”, and I was an intern at Baltimore Center Stage. When was that, and what was the moment for you when you thought, “I'm a director”?
Cheyenne: What's interesting is I did quite a bit of it in high school because we had directing courses, we had a full theatre intro to everything. We had opportunities to direct in our little black box theatres, so I had that under my belt going into college, and then I honed in on playwriting. I realized I didn't do any directing or assisting in my undergrad; everything was pigeonholed into playwriting. I had to do the new work development stuff, so I had that tool, but I didn't get a chance to really apply it until I got the call to assistant direct at Philadelphia Theater Company; that was a production of The Mountaintop, and the director was Patricia McGregor. That process was so incredibly enriching because just watching Patricia work really allowed me to keep that door open – that I'm not just a playwright, that I actually have this skill set that also needs nurturing, as a director. I encourage young people and folks who ask me how to get started, I encourage them to make work with their peers. The momentum was built by being in these different artistic ensembles. It's hard to describe it. Many of those were housed at the Painted Bride. The Painted Bride has always been a home for artistic collaboration and fusion, of grabbing folks and putting them in a circle, and by the end of their time together, they have created something beautiful. Word of mouth started to create more opportunities…”Oh, Cheyenne, I saw this thing. I have a play. I'd love for you to read it. I'd love to sit with you, see if you would direct it.” And it started with little festivals until larger theatres started to call and say, “Hey, we have this play, we'd love to talk to you. We have this new play festival. We'd love for you to direct in it.” I've done very little assisting. I've really fallen into it. It's one of those things that I think is cool to say out loud, but I also do feel the gap in that. I feel the gap in not being able to observe a lot of directors' processes. I feel like directors are kind of in these silos, and it doesn't have to be secretive, and we don't have to feel alone in solving these plays and these productions and these dynamics. We don't have to create in silos. And that's why I am also on the board at Directors Gathering (DG), which is an organization for the development of directors at all stages of their careers. The organization exists out of Philly, but right now we have board members across the country. It's an opportunity for us as directors to get together and just be like, “Hey, we're not creating in silos. Let's actually do some professional development. Let's do some skill sharing. Let's really get some resources for each other and some affinity space for each other”.
Jacob: You were part of our artistic staff at Long Wharf Theatre, which was such a gift. You have been a champion of August Wilson from the beginning, and specifically of this play. What is it about August Wilson, given that you yourself are a playwright, what is it about his work that speaks to you and to your artistry?
Cheyenne: August Wilson is, in my humble opinion, a once-in-a-lifetime type playwright. He is my Shakespeare. I think he's America's Shakespeare. What I love most, and this is not a critique of the canon of Black playwrights, but what I love most about August Wilson's work is that we get a snapshot of the working-class blue-collar African American experience that doesn't center conflict. It is not our proximity to whiteness or our oppression by white America, so we get real life. And it's not contrived. And it's not flashy. It's a home-cooked meal. And that's how I view August Wilson's work. When I read it, when I see it, I feel like I've just had a home-cooked meal. At someone's grandma's house. On a doily tablecloth. And I can smell the wood in the room, because there's so much wood furniture that you can smell the wood polish. That's what reading his work and experiencing his work is like. So that's why August Wilson.
Jacob: August Wilson created the American Century Cycle, which chronicles the African American experience through the prism specifically of Pittsburgh. And Gem of the Ocean is the first in that cycle. What is it about Gem of the Ocean that really speaks to you as an artist?
Cheyenne: As a person, I’m someone who walks with my ancestors. I'm someone who, in my formative years, I've had five grandmothers living at one particular time, and sitting at the feet of my aunts and my grandmothers and their friends and hearing their stories. I feel like I know Aunt Ester. I feel like I've always been prepped to be Black Mary. So that really resonated with me, the matriarch play. How all of these people defer to this woman, to this matriarch, and how she shoulders the burden, it always resonated. As an artist, to have the opportunity to make the ancestral plane. To bring it alive. To know that I can bring it to the stage. To know that he's not just asking us to acknowledge its existence, but to journey there in this play. That is what is most tantalizing about this play, because I have often dreamed about what's behind the veil. I've often dreamed about who's waiting there. What will we find? It's an honor to be able to see – to make the dream in my head a reality.
Jacob: August Wilson and his work have a deep resonance with the New Haven community because a lot of his work premiered in New Haven. As we head into our first rehearsal, talk to us a little bit more about your vision that you're going to deploy for this community, and for your actors and your designers.
Cheyenne: I think that we start with the canvas that we have, right? We're not in some black box where we're inventing the world around us, really. We're in the Boathouse, and the Boathouse has these windows that look out into the water. So first, I'm inspired by bringing the water in, by not shying away from it, by not hiding the natural light that we have, but embracing the outside and pulling it into the space. Aunt Ester's home is mystical, and it is more than it seems. By allowing the ocean to be omnipresent, which is symbolic of journey, symbolic of cleansing, symbolic of the boundary between life and the afterlife, and life in the ancestral plane, we should feel the essence that this home is more than meets the eye. Starting there, the vision is that we are in a home that is more than meets the eye. We are going to meet a host of characters who all have their own interpretation of what freedom is for them as individuals, and who all have their own perception of how that goal is achieved, how that freedom is achieved. I am someone who's deeply inspired by ensemble work – really finding the connection and the physical storytelling that can happen among these characters in this place without getting too in the weeds of performance. How is this week different from any other week at Aunt Ester's house? How is this different? How is the arrival of Citizen Barlow different from any other person coming to wash their soul? That is the essence of what we're going to uncover together as an ensemble. What physically allows us to feel different? When there are threats, we feel the boat rock. Is it that in transitions we can feel the creak of the ship?
Jacob: Part of what I think will be really beautiful and arresting in your vision is the thing that you've talked about from the beginning, which is to develop a kind of movement vocabulary that helps tell the story and amplify the text. I'm also really grateful that you're naming the location of this production. We're an itinerant company, where we make theatre in spaces all across the city, and we're always thinking about how the container fits the story, and in my mind, there's no better place than the Boathouse that overlooks the Long Island Sound. The space speaks so perfectly to August Wilson's Gem of the Ocean, and I'm excited that you and the designers are thinking about all of the possibilities of that. You spoke to it a little bit when you said he's your Shakespeare, and my sense is that August Wilson's plays are a sacred text. I also love that you're naming the way this sacred text explores real people. These are real people; it's not rooted in trauma, it's rooted in possibility. And what it means to dream and what it means to be a community. I almost think that it can be intimidating to work on an August Wilson play because he is so revered, because it is a sacred text, because he is your Shakespeare. How are you navigating that?
Cheyenne: What I had to do was put the theatre training down. Right? The thing that makes it daunting, the thing that makes it sacred, and lean into the fact that he's talking about my people. I come from Waterbury, which is a town not unlike Pittsburgh; it's small and not metropolitan, but it is an industrial factory town. Waterbury, in its heyday, was the brass mill capital, and now it is a ghost of that memory. At first glance, it feels daunting, and then I realized that he's talking about my people. He's talking about where I'm from. He's talking about my great-grandmother, who took people into her home, who cleansed them, who washed their souls, who was the choir director for sixty years at her church. He's talking about my mother and sisters and aunts who fed us meals and took care of us and turned down our beds and sheltered everyone's children. He’s talking about everyone's down-and-out cousin who just needed a place to rest their head until they're back up on their feet; he's talking about my people. So it actually was more homey than anything else. August Wilson's Gem of the Ocean feels like home to me. It doesn't feel like an inaccessible, artistic, heightened experience. It's home. And I'm from Connecticut, so we’ve got the water.
Jacob: I love that. Because what I'm hearing you say is that you're going to enter this process from a really personal point of view, that to your point, “that these are my people, this is my story as much as it is Wilson’s”. Wilson wrote this story to reflect your community and other Black communities, so put away the book around structure, and Aristotle and all that – it's more about what you know in the heart versus the head.
Cheyenne: Yes, and I believe that August Wilson wrote his work for his people, so to convolute with theatrics for theatrics' sake is, I think, further away from the vision. I think we can alienate those blue-collar audiences that he's reflecting in his play.
Jacob: Yes, and you know, there's a kind of accessibility to the story. Even though he's speaking to a Black African American audience, it is also rooted in the American experience. The work is so specific and yet so universal, and I think that's why he is becoming America's Shakespeare.
Cheyenne: I think the brilliance of his work is that if you fight against the language, you will do a disservice to yourself. You have to embrace the language and embrace the vernacular. It's very specific. And that's the challenge, right? You’ve got to do your homework with August Wilson because he's not necessarily saying it plain, but he's saying it how we say it. So, if you fight the language in this piece, and you don't understand the rhythm and the syntax of these characters, you're really going to get lost in the granulars of the conversation. And there's some meaty text there, but it is accessible if you know how to approach the work.
Jacob: This show closes out our 61st Season, and I love that you are returning. I hope you feel like Long Wharf Theatre has become an artistic home for you as you think about how you started with Play On My Block, and then doing a world premiere, and now doing this classic play. I feel like your work always has a message to it for our audience. And so I'm wondering, what's the message? What do you want the audience to walk away from after seeing your production of August Wilson's Gem of the Ocean? The beauty of theatre is that people are going to walk away with different things always, but what do you hope people leave with?
Cheyenne: The immediate word that comes to mind is freedom. And specifically, I would hope that someone feels inspired to get free. Free from that thing that they just can't shake, that burden on their shoulders, that hurdle that is just debilitating, and keeping them from that next rung in reaching their goals. I hope that folks can leave the play knowing that they can put that burden down. That freedom is individual, as much as it is communal. And that they must now go seek to find that. I hope there are folks who seek to find their own freedom within themselves and freedom within their people, whatever that may be, and whatever path that might lead them down. Because I, too, have to put some burdens down to sit in this. In this rehearsal room next week, you know, I'm gonna have to put some burdens down myself.
AUGUST WILSON CELEBRATION
- Sep 16 2025 - Jun 15 2026, 7:00pm