The “Slave Play” actress and the Chicago-based artist discuss generational gaps, success and the art that brought them each acclaim.What does it mean for an artist to be free? And what does that freedom look like for a contemporary Black artist? Amanda Williams has recently been asking herself these very questions. A Chicago-based visual artist who trained as an architect, Williams, 47, is known for her pieces exploring the nuances of color, both racial and aesthetic. Her breakout work was “Color(ed) Theory,” a 2014-16 series in which she painted eight condemned houses on Chicago’s South Side in vivid, culturally coded shades, such as “Ultrasheen,” a dark turquoise that matches the hue of a Black hair-care product, and “Crown Royal Bag,” a purplish pigment that mirrors the packaging of a popular whisky.In a 2018 TED Talk, Williams discussed how we perceive color — specifically, how our perceptions are determined by context. One example, she said, was redlining — federal housing maps from the 1930s marked neighborhoods inhabited by Black Chicagoans as red, contributing to policies that prevented many residents from securing loans — which weaponized color and resulted in underinvestment. When the actress Joaquina Kalukango, 32, heard the speech, she was awe-struck. Kalukango is no stranger to powerful works of art: Last year, she received a Tony nomination for best leading actress in a play for her work in Jeremy O. Harris’s searing, passionately debated drama “Slave Play,” which is set on a plantation and follows a trio of modern-day interracial couples whose relationships are stymied by conflicting views on race.One rainy morning in October, Kalukango met Williams at the latter’s studio in Chicago’s Pilsen neighborhood. Kalukango was days away from starting a Chicago run of “Paradise Square,” a musical about the 1863 Manhattan draft riots, in which Irish immigrants turned on the Black neighbors with whom they’d previously peacefully coexisted. (It’s headed to Broadway early next year.) Meanwhile, Williams is expanding on “What Black Is This, You Say?,” an ongoing, multiplatform series of abstract paintings inspired by cultural touchstones and observations related to the Black experience that she showed at Art Basel in Miami Beach this month.Amid laughter, Williams and Kalukango talked generational differences, the desire to be “regular” and the blurry line between artistic genius and madness.AMANDA WILLIAMS: Twenty twenty was a mess. I was contemplating Kool-Aid [the subject of one of her latest paintings] and laughing about it, and then the whole world was like, “How are you feeling about being Black, segregation and systemic racism?” People were like, “I want to help, right this minute.” I thought, “I don’t know how I feel right now. I was actually doing something else, and now I’m going to cry.” It’s a little easier now. We’re farther away from it. How did that feel for you?JOAQUINA KALUKANGO: It’s interesting, because “Slave Play” opened [on Broadway in October 2019] before the country had its racial awakening. There was a lot of aggression toward our production. There was a lot of pushback, specifically within the Black community. [Some who had seen the play, and many others who hadn’t, found it offensive in its use of antebellum role play and inappropriately sexually graphic; one online petition calling for the show’s shutdown referred to it as “anti-Black sentiment disguised as art.”] But after audiences saw the show, there was so much conversation. On the streets, people would come up to me and talk about it. That was affirming. It was also exhausting. The greatest thing that helped me was when we had a “Black Out” night — the audience was all Black. I heard the show in a different way: It was funny. There was this release of Black people finally being able to feel like this show was for them, as opposed to sitting next to someone and wondering, “Why are you laughing at this?” How can we get Black people to feel free regardless of who’s sitting next to them? How can we fully enjoy ourselves in situations and experience art without feeling like other people are watching us? It’s always a struggle.Kalukango in “Slave Play” at the Golden Theater in New York City, in September 2019.Sara Krulwich/The New York TimesA.W.: I’ve thought a lot about the freedom question. Take Kanye West. He’s obviously experiencing some mental health issues. But also, he has a level of mastery and talent that borders on complete freedom. He says inappropriate things, and maybe he doesn’t even understand what freedom is. But if you’ve ascended beyond practically any other brown human you’ve ever met, and you can buy Wyoming, isn’t that free? [West has purchased two huge ranches there.] He just does what he wants. [For the listening party for “Donda,” his recent album named after his mother, who died in 2007,] Kanye was like, “I’m going to recreate my mom’s house in [the Chicago Bears stadium] Soldier Field.” Everybody was confused. But I thought, “This could be a mental moment, but it’s also pure creativity.” Every artist who you might say is the most free, in terms of pushing their craft to the edge, is always called crazy.J.K.: Did anyone tell you, early in your career, that you had to work within certain boundaries? Did you feel pressure to be a certain type of artist?A.W.: I trained as an architect [at Cornell University]. My parents were in a panic that I might be an artist. They were like, “Artists who make money are called architects.” In a sense, that was a boundary. Then, I moved to the San Francisco Bay Area right at the height of the dot-com boom. The economy was great. Projects were bountiful; jobs were plentiful. I was able to live out this architectural career that I thought would take 30 years in five or six. Then I had a boss who said, “If you could be doing anything in the world right now, what would it be?” She thought I was going to say, “Taking over your company.” And I said, “Painting.” She encouraged me to try it. And the Bay Area lent itself to that. Everybody had an idea. Google was born when I lived in the Bay. That kind of environment helped me take the leap.If I had to do it again, I wouldn’t. I’d be like, “What if it doesn’t work? How am I going to eat?” But back then, I was just like, “Oh, I’ll eat some avocados, it’s California.” There’s no moment I remember when somebody said I couldn’t do it. Well, I’m sure there was, but I blocked it out. My friend and I were just talking about how our generation tended to dismiss racist comments or sexual advances. We just kept moving. Your generation does not tolerate nonsense. Is that how it feels?J.K.: Definitely. The new show I’m in, “Paradise Square,” is a musical that has been in development for a long time. There was always a struggle to figure out whose lens the story should be told through. Now, it finally centers around this free Black woman in New York who owned a bar in 1863 [Nelly Freeman, the role Kalukango is playing]. We have an E.D.I. [equity, diversity and inclusion] person who talks about terminology. One day in rehearsal, an assistant said, “Joaquina, we’re not going to say the L-word in this sentence.” I was like, “ ‘Let’? ‘Listen’? ”A.W.: Which “L”?J.K.: It was “lynch.” I said, “What? We’re just not going to say this?” But the idea was, we don’t have to say that word until it’s absolutely necessary. I thought, “Well, this is a whole new way of being, even for me. That word doesn’t bother my spirit, but it’s bothering other people’s spirits.” It’s a different world from when I was growing up in Atlanta.Loren ToneyA.W.: How does that impact your craft? Does it trip you up to have to be mindful of words in a way that maybe you hadn’t been before?J.K.: We’re all more careful. Everyone’s fragile. We’re still in the midst of a pandemic, and so many issues have come up for so many people. We’re all giving each other a lot of care and grace in this new era that we’re trying to build, this new era of theater we’re trying to make. But it’s a bit of a struggle, I’ll be honest. When you do work that’s specifically about a very troublesome time — and if you look at the Jan. 6 riot [at the U.S. Capitol], it’s similar to the draft riots — you can’t sugarcoat it. You can’t run away from it. It’s always a balance of, how do you tell a story without traumatizing our community?T: When did you first encounter each other’s work?J.K.: I first saw Amanda’s work in her TED Talk.A.W.: Oh my God. I had wondered, how did you find out about me? How do you know who I am?J.K.: I had such a visceral reaction to “Color(ed) Theory.” All of it was so much a part of my life, my childhood. Plus, I just love colors. How did you get that concept? What inspired you?A.W.: I grew up on Chicago’s South Side and crossed town every day to go to school. Chicago segregation, coupled with the city’s grid, is perfect for systemic oppression because it sets boundaries, and then we mentally reinforce them. I was hyperaware of color all the time, as in race, thinking, “That’s a Mexican neighborhood.” “Chinese people are there.” “White folks do this.” Things like that. And I’ve loved [chromatic] color since birth. Then I learned about color in an academic setting.One summer, while [I was] teaching color theory, a friend joked, “They pay you money to teach people what? Red and blue is green?” I said, “No, color theory is a whole science.” She said, “You know colored theory.” We laughed and I left it alone. A week or two later, I thought, “I do know colored theory.” I spent another few years making sense of it. It seemed so juicy. I started to think, “What things make you think of the color first?” There’s a story I told in the TED Talk: I met a gentleman who grew up near the “Crown Royal Bag” house. He thought the purple house meant Prince was coming. Even after I told him about my art, he said, “You wait and see. Prince might show up and perform right here.” Suddenly, he had hope for that vacant lot, in a way that maybe he didn’t before. To me, that was success.J.K.: It was brilliant.A.W.: At first, I wasn’t as familiar with your work, but when I started to look into it, I was like, “How could I have missed all of this? These are the exact same things I’m thinking and talking about.” I’m excited about how we translate these thoughts across mediums — theater, performance, music, architecture, sculpture, writing.Williams’s “Color(ed) Theory: Pink Oil Moisturizer” (2014-16).Amanda WilliamsWilliams’s “Color(ed) Theory: Crown Royal Bag” (2014-16).Amanda WilliamsT: You both have long been working artists, but your breakout pieces — “Slave Play” and “Color(ed) Theory” — made you famous. Has that affected your work? Do you feel an added responsibility now?J.K.: An actor starts off auditioning for nearly everything. We’re told “no” 99 out of 100 times. Initially, the roles I took were just what ended up coming to me. But I also believe that what’s for you is for you. When you’re on a path that you’re aligned with, more things start coming your way. Now I am adamant that Black women see many facets of ourselves, that we are depicted with a wide gamut of emotions: the unflattering and unraveling parts but also joyful and loving, peaceful and gentle. I want it all for us, at every possible moment. I’m trying to ensure I show Black women as full human beings — not stereotypes, not archetypes. We’re not strong all the time. Yes, our ancestors had to survive, but there was always joy in the midst of all that pain.A.W.: You also have to give yourself permission to be an artist. That’s hard because there is a burden. You know how few people have the same opportunities, so you always want to make sure you’ve done justice. At the same time, you have to take the pressure off. Our society thinks about the home run, the slam dunk — the idea that each thing you do must be better than the last. But if you look at any creative being’s full oeuvre, there are ups and downs. Artists have to continue to understand themselves and improve their craft for themselves. It makes me think of this great artist Raymond Saunders, who lives in the Bay Area. He taught an advanced painting class, and I was teaching at the same school, so he invited me to his class. I went — and the students were eating handmade pastries from this beautiful boutique in Berkeley or something. I’m like, “What is this?” And they’re like, “He told us he can’t teach us how to paint, he can teach us how to live.” It was mind-blowing. Maybe we don’t have to nail it every single week of every year. Maybe we just nail it every five years. Maybe we can sleep one of those years.J.K.: I always think, “Do we ever have the space to be mediocre and figure things out?” I don’t want to be Black girl magic every day. Sometimes I want to be regular. Just regular Black. [All laugh]A.W.: Regular Black. I’m going to make a painting based on that.T: How do you two define success right now?A.W.: Just being the best me. I don’t worry so much if my work is well received or if it garners accolades. That sounds so cheesy. My husband jokes, “Well, that’s nice to say after you’ve gotten the accolades.” [All laugh]J.K.: I love originating and creating new roles. For me, success is knowing that there are girls coming up who can use work I’ve done as audition pieces for colleges. In “Slave Play,” my character, Kaneisha, has a 10- or 15-minute monologue. She takes up space for almost the entire last act. I’d never seen anything like it onstage before. For a long time, it was hard to find material or scene work that included multiple Black characters. It was hard finding those plays [when I studied at the Juilliard School]. It’s all about the next generation for me. If at any point I can make someone feel more free, more confident in their abilities, that’s the win.This interview has been edited and condensed. More