Emann Odufu speaks with the artist about vulnerability, portraiture, creative freedom, and what it means to capture not the icon of the past but the person she has become.
When MTV Unplugged No. 2.0 aired in 2002, I was too young to fully understand what I was watching. I only knew that it felt different and important. Years later, revisiting the performance ahead of this interview with Tomokazu Matsuyama about his recent portrait of Ms. Lauryn Hill, I realized it was one of the defining cultural documents of its generation. It marks the moment Ms. Hill’s public role expanded beyond that of an artist into something closer to a philosopher and an icon, wrestling with questions of identity, faith, creativity, commerce and freedom. To make a portrait of Ms. Hill today is to reckon with that evolution.
It was with that history in mind that I arrived in East Hampton to witness her performance with the Murmrr Arts Foundation. The evening opened with a largely acoustic set that returned to material from Unplugged that she has revisited only sporadically over the years. Gradually, the music drew the audience back into the psychically dense world from which those songs emerged. But as the performance developed, it became clear that we were not revisiting that moment so much as witnessing what felt to me as its resolution. The relentless self-examination that once seemed to define that period now felt transformed, carried with the authority of an artist decades further into her journey. This is the Ms. Lauryn Hill that Tomokazu Matsuyama painted. Onstage, that transformation became palpable to the audience, and in Matsuyama’s portrait, it became enduring.
Before a single brushstroke had been made, Ms. Lauryn Hill and Tomokazu Matsuyama independently selected the same contemporary photograph from the Met Gala as the basis for the portrait, a moment of synchronicity that became the foundation of their collaboration. That spirit of dialogue carries into my conversation with Tomokazu, which extends well beyond music and painting. Together, we explore portraiture, vulnerability, collaboration, and what it means to inherit a legacy that is still unfolding.
EMANN ODUFU: At first glance, you and Ms. Lauryn Hill seem to come from very different creative worlds, yet this collaboration felt remarkably natural. Why do you think that is?
TOMOKAZU MATSUYAMA: Although we are almost the same age, I pretty much grew up listening to her music, especially her work with the Fugees. So, when this opportunity came along, it didn’t feel like just another commission. The collaboration really became real when we were selecting the image for the portrait.
Because the timeline was short, I began looking through photographs myself. I kept returning to a recent image of Lauryn from the Met Gala. I wanted to paint Ms. Lauryn Hill as she exists today, not simply recreate the image everyone remembers from the late 1990s. Before I had the chance to send my selection, Lauryn sent over the photograph she wanted me to use. It was the same image. Mine was a slightly wider version. Hers was more tightly cropped, but we had independently arrived at the same photograph. That felt like a real moment of synchronicity. It told me we were already imagining the portrait in a similar way before we’d even begun discussing it. After that, everything flowed very organically.
EMANN: That moment says something interesting because the collaboration didn’t begin with the painting itself. It began with a shared act of seeing. Rather than choosing an image from the height of Lauryn’s fame, you both gravitated toward a contemporary photograph. What drew you to that?
TOMOKAZU: I didn’t want to paint the Lauryn Hill everyone already remembers. Over time, her character has evolved. She’s lived through so much personally and creatively. I wanted to paint Ms. Lauryn Hill as she exists today. That felt much more truthful than simply recreating an image people already carried in their memories.
EMANN: Although your practices work through different mediums, I kept thinking there were deeper parallels between them. Where do you see your work meeting hers?
TOMOKAZU: I think it’s vulnerability. Ms. Hill changed hip hop because she was completely herself. She embodied confidence and vulnerability at the same time. She wasn’t trying to fit an existing mold. Her contribution ultimately became greater than her influences. As an artist in America, I understand that feeling. You have to trust your own voice. Her independence and belief in herself became incredibly influential for me, and that’s something I hope exists within my own practice as well.
EMANN: Portraiture has historically been tied to power and legacy. What role does portraiture play today, when images circulate instantly through social media?
TOMOKAZU: Portraiture used to function almost like Instagram does today. Kings and aristocrats commissioned paintings to project power. Today we already do that ourselves through our phones. That means painting has a different responsibility. When I approached Lauryn’s portrait, I didn’t want to over glamorize her. I wanted to understand her artistically and express what she has contributed beyond celebrity, her generosity, her independence, her strength, and the way she brings people together. Rather than constructing another image of power, I wanted to create something rooted in humanity.
EMANN: Beyond Ms. Lauryn Hill herself, what visual decisions shaped the painting?
TOMOKAZU: I wanted the symbolism to remain simple. I introduced the moon, the sun and peonies. The moon and sun exist together to suggest infinity, the continuous cycle of time, while the peonies might suggest sensitivity and blessing. I wanted the symbols to remain open and to leave room for personal interpretation. I also wanted the atmosphere of the painting to carry much of the emotional weight. The color itself becomes part of the portrait’s language rather than simply describing Lauryn’s appearance.
EMANN: Millions of people already feel they know Ms. Hill. How do you paint someone who already exists so powerfully in the public imagination?
TOMOKAZU: I tried not to paint what she’d already created. I wasn’t interested in recreating the imagery people already associate with her career. Instead, I spent time listening to her interviews and public conversations. I wanted to understand why she returned. What was she trying to say now? If I simply painted her past, I would have armored her with history. Instead, I wanted to paint the person speaking today. Now my Instagram is just Lauryn Hill every day because I searched for her so much.
EMANN: That happened to me too. My entire feed became Lauryn Hill interviews.
TOMOKAZU: Right? Her commentaries are incredibly powerful. I find those just as inspiring as the music.
EMANN: This collaboration naturally brings together music and visual art, but the idea of creative fusion seems to run throughout your practice. Why do you think your work continually moves across disciplines?
TOMOKAZU: Honestly, it never felt unusual to me. I didn’t really think about it that way. I didn’t go to art school, so I never inherited the idea that disciplines should remain separate.
Working alongside musicians, designers and performers simply felt natural. Music has always shaped my creativity. When you’re painting, your ears are the one sense that remains completely free. I’ve always been interested in collaborating with people whose work moves audiences differently than painting does.
EMANN: It also feels like those collaborations expand what art itself can do.
TOMOKAZU: Absolutely. Visual art reaches one audience. Music reaches another. As painters, we might spend a year creating a single image. A musician can move thousands of people in just a few minutes. When different creative languages come together, the work begins to occupy people’s lives differently. It reaches not only the eye, but the ear, the body and the emotions. That’s what continues to excite me about collaboration.
EMANN: Murmrr Arts Foundation seems like a place where artistic communities that don’t usually intersect can meaningfully meet. This collaboration feels like an embodiment of that idea. Having experienced it firsthand, what do you think the foundation’s vision makes possible that more traditional institutions often struggle to create?
TOMOKAZU: I think Murmrr Arts Foundation understands something that’s becoming increasingly important. Contemporary culture isn’t divided the way institutions often are. Popular culture is part of cultural history. One day museums will present today’s music the same way they now present historical prints or paintings. The things we experience today will eventually become part of our cultural record. Organizations like Murmrr Arts Foundation, help to create that record. What excited me about this project wasn’t simply painting Ms. Lauryn Hill. It was participating in a moment where music, visual art, philanthropy and community all came together. At the event you saw children, older generations, collectors and music fans sharing the same space. Those moments don’t happen by accident. They happen because someone believes these creative worlds belong in conversation with one another. To me, that’s what this collaboration represents.
EMANN: How do you hope someone encounters this painting fifty years from now?
TOMOKAZU: Every painting becomes a time capsule. The materials, the colors, even the canvas carry the feeling of the era that produced them. I can’t control how people fifty years from now will interpret the work, but I hope they’ll recognize it as something that belonged honestly to its own moment.
EMANN: Finally, what advice would you give the next artist asked to paint an iconic figure? How do you paint a legend?
TOMOKAZU: Don’t paint what they’ve already created. Don’t paint the fame. Don’t paint the success. Try to understand what they represent philosophically. The responsibility of portraiture today isn’t to repeat someone’s public image. It’s to reveal something deeper, to connect ideas in a way neither the artist nor the subject has fully seen before. Emotion has to remain at the center. If you become distracted by validation, the work loses its honesty. It’s easy to be timely. It’s much harder to become timeless. But in order to become timeless, you first have to be truthful to your own moment. That’s what I try to remind myself whenever I begin making work.
