Regina King on Caught Stealing, Grief, and the Finding Joy Again

Photo Credit: Brian Bowen Smith 

BY LAURA SCHREFFLER

PHOTOGRAPHY BRIAN BOWEN SMITH

STYLING CHARLESE ANTOINETTE

HAIR LARAE BURRESS

MAKEUP LATRICE JOHNSON

SHOT ON LOCATION AT MOTHER WOLF LOS ANGELES

The first thing Regina King tells me is that she knows nothing about the Lower East Side dive bar scene of the 1990s, back when KGB Bar reigned supreme — and frankly, she’s fine keeping it that way. “You’re talking drip-tray shots? I can’t! That makes me uncomfortable,” she laughs, recoiling at the thought. “When it comes to consuming something insanely unsafe or gross, I just can’t.”

But don’t mistake her squeamishness for softness: just because she won’t ingest anything that isn’t fit for human consumption, King herself has all of the grit and gumption of a New York City cop, which is, incidentally, the part she plays in Caught Stealing, Darren Aronofsky’s upcoming dark, propulsive dive into 1990s New York, out August 29 from Sony Pictures Releasing.

And while she may not have frequented Manhattan’s most iconic divebars of yesteryear, King isn’t entirely unfamiliar with the vibe of early ‘90s New York. She made the move from her native Los Angeles to Brooklyn for a stint — around the time that Boyz n the Hood was hitting theaters —armed with the dream of seeing her fashion line, designed to discreetly carry blunts, take off. Yes, really.

The now-54-year-old Oscar winner takes a trip down memory lane, telling me about her days living in Riverdale — a residential neighborhood located in the Bronx — and, before that, Brooklyn, where she posted up with friends for a month while trying to get her green venture off the ground.

“We had this clothing line called Smokawear that was geared towards the green smoking community that we were starting to market; we were going to sell it and get it on TV shows,” she recalls. “Some of the pockets were designed so that you could put a blunt or a joint in them, but we had [a lot of variety] — vests, jeans, dresses. We just kind of decided, ‘OK, we’re in our 20s, let’s just do it. I was financing it myself. We started in LA, but all these other kinds of similar brands like Walker Wear started to come out, and we were like, ‘New York is the place to go.’”

Photo Credit: Brian Bowen Smith

Was the line a success? King says she’ll never know, because her acting career started to take off, she got married, became a mom, and “grew up” — but Smokawear still lives on via old episodes of Def Comedy Jam (Martin Lawrence wore one of the vests), and photos from a fashion show she put on where Vivica A. Fox and Tichina Arnold both modelled her designs.

I pause to consider that in the 1990s, the green community was vastly different than it is today (marijuana was illegal in New York until 2021) — which reminds me that the woman in front of me today — who is Zooming from Cincinnati, Ohio — is a total badass, utterly and unapolagetically herself. So, it makes sense that she would be drawn to this kind of role — playing Roman, a relentless beat cop caught in the fallout of a brutal murder — and that she would prepare for it by studying and learning from another total iconic badass — none other than Jackie Brown. Yes, the Jackie Brown.

I had previously thought Jackie Brown was a fictional character created by Quentin Tarantino’s beautiful brain, but King swears that Jackie is real —and the basis for her Caught Stealing character. “I was approaching it through her lens, you know? Seeing pictures of her and talking to her, I could see how I could have known her. She’s about 10 years older than me, but her presence is so strong, and so of the neighborhood; so real.”

King says this mythical meeting was forged by the magical Darren Aronofsky, who not only found Brown, but created a space for she and King to meet. “Darren is the truth,” she compliments, noting, “It’s interesting: you can be a fan of someone’s and never have met them, or meet them and realize that you don’t want to spend three months of your life with them. But when I heard there was interest in me for this role, [I knew I had to meet him in person].”

Although she was initially on her way to Barcelona, King made a detour in New York for a face-to-face, one-on-one meeting. “I felt an instant connection,” she remembers. “I was very clear of the story that he was going to tell, and I was also very clear that this [story] was out of his wheelhouse, and not what people would expect from an Aronofsky film. I’m so with that, going outside of the expected box.”

That’s King for you, too. She’s built a career by going against the grain at every turn — refusing to be typecast, overlooked, or boxed in. She broke out on 227 as a teenager and never faded, transitioning seamlessly into powerful roles in films like Boyz n the Hood, Ray, and Jerry Maguire at a time when Hollywood rarely gave Black women that kind of range. While others chased commercial fluff, King leaned into nuance and complexity — earning four Emmys for roles in American Crime, Seven Seconds, and Watchmen, where she played a masked vigilante grappling with race, justice, and grief. She could have coasted on acting success alone, but instead stepped behind the camera, directing episodes of Scandal, Insecure, and This Is Us before making history with One Night in Miami, becoming the first Black woman to debut a film at the Venice Film Festival. That movie alone earned her Golden Globe and Critics Choice nominations, cementing her status as a creative force, not just a performer. She’s portrayed trailblazers like Shirley Chisholm, and more recently directed and executive produced Forever — a tender, teen-centered adaptation of said Judy Blume novel for Netflix, which has already been picked up for a second season. She’s also in the midst of shooting Children of Blood and Bone, the long-awaited, highly anticipated film adaptation of Tomi Adeyemi’s bestselling YA fantasy novel (she plays a pivotal role as Queen Nehanda). In short: Regina King didn’t follow the Hollywood playbook — she wrote her own.

That fearless, unorthodox spirit shows up in Caught Stealing too — not just in King’s performance, but in the way the city itself is shot. Because in this story, New York isn’t just the backdrop — it’s the co-star (alongside other living, breathing individuals such as Austin Butler, Zoë Kravitz, Matt Smith, Liev Schreiber, Vincent D’Onofrio, Griffin Dunne, Bad Bunny, and Carol Kane). It’s gritty and raw, full of contradictions and beauty and danger, just like the characters navigating it. In this film, you can feel the pulse of downtown, the dirt under the fingernails, the soul of a city that shapes you whether you like it or not.

For her part, King fell into the former camp: she was a fan. “We were actually able to shoot at a diner, a coffee shop, that’s [been in existence prior to the ’90s],” she recalls with enthusiasm, noting, “In that sense, New York becomes a real character in the film. And it makes sense: Darren is a New Yorker to the end, and he was definitely able to capture the New York that doesn’t exist anymore, recreate that ’90s feeling, without a bunch of CGI.”

Like that version of New York, many of the worlds King explores — whether it’s Miami in the civil rights era, a congressional campaign trail, or the realm of YA fantasy — are shaped by friction, identity, and reinvention. And in each of them, she brings the same grounded truth.

And maybe that’s because at this point in her career, with all the accolades she’s received since her start at age 14 (yes, you read that right) in the television sitcom 227, she’s in the sweet spot of being able to make career choices for herself and only for herself. Naturally, that feels about as damn good as can be expected.

“It feels great that I am financially sound enough to be able to do that,” she admits. “It’s a blessing, because at the end of the day, you have to have a certain relationship with money to be OK with working this way. There are some people that just have this blind faith where they know they’re always going to be alright. I am one of those people who does think about money. I don’t want to say that I worry about it, but I do think about it, and I am grateful to be in a place where I can say, I’m not doing that. That truly is a blessing.”

These days, what moves the needle when it comes to project selection, is simple. “I choose the people I want to work with, whom I want to tell stories with. I love being in a position to help cultivate and create a space for younger storytellers. It feels good to be in a position to exercise that.”

Photo Credit: Brian Bowen Smith

That clarity spills into everything — even how she spends her afternoons on set. When I ask if she and her very talented slew of younger storytellers from Caught Stealing ever ventured out on the town together between takes or after the day had wrapped, she laughs and insists the cast stayed focused. But when she isn’t working, King definitely knows how to let loose — within reason.

“I’ll hang in a bar,” she allows. “Maybe I could do three with a drink at each one — but my bar-hopping days are a long way behind me.”

Which, honestly, tracks, because these days, King is all about raising the bar. She’s not chasing scenes anymore — she’s directing them, producing them, or absolutely slaying in them.

And drip-tray shots? Whether it’s the Lower East Side or anywhere else, she’ll pass (and not in a puff, puff way, either). She’s been about that life before (let’s not forget about the clothing line with pockets made for blunts!), but King isn’t here for the party anymore. She’s been there, done that, and (out)grown it beautifully. She doesn’t need to relive the past to prove anything to anyone — especially not when she’s in a place to decide how the story goes.

Photo Credit: Brian Bowen Smith

IN REGINA KING’S WORLD, joy and pain aren’t opposites — they’re partners. She’s found that it’s not only possible for contradictions to coexist, but that some of the clearest truths live in the tension between them. Over the course of our conversation, she speaks not in absolutes, but in nuance — about presence and loss, control and surrender, softness and strength. There’s no performative wisdom here, no tidy answers. Just an artist — and a woman — who’s learned how to live in the gray, and who’s still figuring it out in real time.

That lens — of finding clarity in contradiction — colors everything. Success. Spirituality. What it means to show up for people. And as our conversation deepens, she starts pulling threads — about change, about survival, about the kind of growth that doesn’t always look the way you expect it to.

As she puts it, “I think that there’s things that have happened along the way in each individual’s life that guides them to make certain choices in the moment, but there are always creeds that you live by. For me, I’d say it’s ‘treat people like you want to be treated.’ And that seems really simple, but I do think good manners go a long way.”

When I express that she must be a good person to operate this way — that selflessness isn’t a given — King seems genuinely surprised. “I think most people that I know have experienced success from the fruits of their labor,” she says. “When it comes in abundance, there’s a natural desire to share.”

As has been established, King is no pushover though: she’s become deliberate about the energy she gives and receives. “I do feel like I’m always met with grace from others,” she says. “I don’t know if that’s what I attract, or if the universe is placing it in my path because it’s what I need — but it’s what I receive.”

She’s quick to clarify: that doesn’t mean she’s immune to the bullshit. It just means she handles it differently. “When those moments happen, I can remove myself from them, and maybe that’s because my circle has become smaller. But it’s easier now.”

That kind of clarity, she admits, came gradually — and it’s still a work in progress. “You asked about the one thing I live by, the one creed,” she says. “But I think it changes. It has to.” She pauses, then starts to trace how and when her outlook shifted. Her perspective started to change five years ago which was, if you might recall, the start of the pandemic.

“So much life has happened since then,” she says, almost to herself, before saying,“This might sound crazy, but I didn’t get that whole cabin fever thing during COVID. I didn’t mind the stillness — I actually found peace in it.”

For many, the pandemic was a nightmare — a time of chaos, loss, and unraveling. But for King, it offered a rare kind of pause. One she now treasures deeply, because not long after, her life would change forever.

Photo Credit: Brian Bowen Smith

During a two-month break from filming The Harder They Fall in New Mexico, she hunkered down at home with her son, Ian Desduné. “We would cook together, he would write music, and time slowed down a bit,” she recalls. “It was nice not to always have a meeting or a call; the stillness wasn’t a bad thing.”

The world outside was spiraling — a global pandemic, the aftermath of George Floyd’s death and the largest racial justice protests in U.S. history, wildfires tearing through the West Coast, Hollywood on hold. And yet, within her walls, there was peace. “Five years ago, I had the understanding that scary and peaceful are not mutually exclusive,” she says. “And now, I understand that sadness and happiness can be happening at the same time.”

That clarity didn’t come overnight. It came in pieces — shaped by time, by heartbreak, by the quiet moments she didn’t yet know would be her last with Ian. Less than two years later, her only child died by suicide at age 26.

Which is why, of course, it makes sense that the pandemic was a time of peace for her. It meant time with her son, time that she will never, ever get back.

I ask if, should she go back in time, these would be the two months of her life she would choose to freeze-frame. And yes, one of them would be. “I know it sounds so terrible, but if I’m being completely honest, it’d be a month there — where Ian was writing so much of his music, that last bit of his music, and I was editing One Night in Miami… and some other things that I want to save for me. And then I’d also freeze-frame the first month of Ian’s life, because I was no longer a home: I was a mom. It was life-changing; it was a feeling I’d never had before in my life. I’ve never felt anything close to it… until he no longer wanted to be here anymore.”
     

It doesn’t sound terrible — it sounds like love, raw and real and bottomless. And no matter how much time passes, she knows it will always be raw — which is why she does not resist the tears that come. They are not performative tears — not gracefully drops poised at the edge of her lashes — but instead, steady, full of real emotion.This is the kind of grief that doesn’t need words to explain itself, but the kind that simply arrives, uninvited and unstoppable.

But in the space where sorrow lives, so does grace. Regina King has never been one to seek silver linings where they don’t exist, but she has learned to reach for the light — even in its faintest forms. “My fortune today was ‘this life is a gift,’” she says. At home, she has a bowl full of fortunes just like that — scraps of wisdom, tiny reassurances that beauty can still break through.

She needs something to hold on to, so she keeps those paper prophecies close — tiny, fragile words offering direction through the ache. They give her a reason to keep creating, to keep speaking Ian’s name aloud.  One of them, in time, became more than just a message on paper. It became an idea she could pour into, shape with her hands, and share with the world. It became a bottle. That bottle became MianU — short for Me and You — an orange wine she launched this month in honor of her son.

     MianU is clearly not a vanity project — instead, it’s a love story. Ian introduced King to orange wine years ago, and now, she’s offering it back to the world in his memory. His name sits at the heart of the label, nestled between the letters like a whisper. The logo is his handwriting. Every bottle is a tribute, a ritual, a bridge between two realms.

“It was kind of an epiphany I had,” she confides, “that came from a place of continuing to create memories in Ian’s spirit. I’m still here, on this plane, separate from him, and I’m surrounded by people talking about their children — engagements, weddings, new chapters — [while mine is gone]. I still love talking about Ian: I just don’t have the chance to create new memories in the way they do. But I’m not focused on that. This is my way of creating something new, together.”

When she says that “it just made sense to start with orange wine. That was him. His art, his creativity — it’s all in there” — there is that one word which gives me pause: start. Maybe this is just the beginning of creating a whole new set of memories.

And so in that sense, this isn’t just a bottle. It’s a moment, a continuation, a way of staying connected, even when everything else says you shouldn’t be. “Every time a cork opens, or every time I’m pouring a glass, I’m thinking of Ian,” she says. “I’m thinking of him 24/7 anyway, but always in this moment, I can see his face. And for people who never got the chance to dance with Ian, maybe they’ll be curious. Maybe they’ll ask. His name is right there, in the middle of it all. He’ll never be forgotten.”

She’s quiet for a long beat. Then, softly: “If you see me, you see Ian.”

It’s not just sentiment — it’s a way of moving through the world. The wine is one expression of that: a tether, a ritual, a new kind of memory. “This wine, for me, is about connection,” she says. “There being a connection in every moment.”

Photo Credit: Brian Bowen Smith

That desire — to stay connected, to feel something real — has become a quiet drumbeat in her life. “I think in life, it’s harder and harder to have those meaningful moments,” she says reflectively. “And that’s why, when I have them now, they feel even more special. We have them less and less as time goes on, and we have to work harder to have them.”

She’s not being cynical — just honest. There’s no armor here, no performance. Just a mother, still grieving.

It’s part of what has changed in her. Not just the grief — though of course that reshapes everything — but a deeper clarity. She lives differently now, with more intention, with more presence. “I one thousand percent live in the moment more,” she says. “I don’t know if that’s something that just comes with time, or with pain, or with the pandemic — probably all of it. But I feel it.”

And if we’re being honest, the pandemic did crack something open. Not in a grand, transformative way — but in subtle shifts. Slowed rhythms and shared silence. It gave her the chance to reflect, to recognize what mattered. “I think everybody learned something huge about themselves during that time,” she says. “Whether it was the biggest bunch of bullshit you’d sold yourself about who you are, or something really profound… [during that time] you learned it.”

For King, the lesson was this: she could still create joy, even in the shadow of sorrow. Even after she should have been broken.

Because at the end of the day, Regina King is not just a teller of other people’s stories: she’s the author of her own. She is a woman who has held grief in one hand and grace in the other, and somehow kept moving forward. Her voice has never been more grounded, her purpose never more personal.

She’s come to understand that joy and grief aren’t opposites, but companions — that you can ache and still laugh, shatter and still shine. She’s learned to carry it all: the weight, the wonder, the memory, the momentum. She’s here, wide open to whatever comes next — with clarity, with courage, and with a glass of orange wine raised to the sky.  

Photo Credit: Brian Bowen Smith