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Life, Values & Legacy: Our Chat with Robert Desiderio of South End Boston

We recently had the chance to connect with Robert Desiderio and have shared our conversation below.

Good morning Robert, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: What are you being called to do now, that you may have been afraid of before?
Since the 1980s, when I first picked up an analog camera, I’ve been drawn to the rhythm of the street—to subcultures and lives lived in the margins or just outside the spotlight. What started as an instinct to document quickly became something deeper: a practice of preservation.

The people in my photographs are not strangers. They’re friends, chosen family—the people I laughed with, ate with, cried with. Over the years, some became famous. Some passed on. But each image is a piece of a living archive, shaped not by distance, but by connection.

This body of work now calls to be seen. And while I prefer to let the images speak for themselves, I’ll say this: the work has found its own path. I’m simply walking beside it, and I’m proud of that.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Robert Desiderio. I go under Dezimade.
To be honest, art runs through everything I do. Whether it’s photography, creating clothing, or shaping someone’s hair, my work is rooted in touch, transformation, and storytelling. I consider myself a materialist—not in the consumer sense, but as someone deeply connected to materials, texture, and the physical world.

I began cutting and styling hair at the age of 13, and I’m still doing it today—not just as a job, but as a ritual. Each time someone sits in my chair, they’re not just receiving a haircut; they’re engaging with my craft, with a space I’ve built through years of intuition, study, and love.

My creativity comes in waves—gestation periods followed by bursts of new energy. One medium always leads to another. I build, I shape, I sew, I photograph. I work with color, with form, with feeling. Construction, fine carpentry, color theory—they’re all part of my language.

In many ways, I consider myself a brand unto myself. A Renaissance soul in a push-button world. Everything I create is tactile, analog, alive. I come from a time when art wasn’t filtered through screens, but lived through hands, heart, and time. And I still live that way.
While I’ve always been deeply rooted in the analog world—film, fabric, form—I’ve recently started exploring new ground with AI and digital storytelling. It’s been a natural extension of my creative spirit, not a replacement for it.

One of the most exciting projects I’m nurturing is a character named Darlene. She was born from my own voice, shaped and stylized, and has grown into something much larger—becoming a vivid, living persona with real traction in underground creative spaces. Darlene offers a raw, humorous, and deeply human view of average life—a mirror to society’s quirks and quiet truths.

Voiceovers, character creation, storytelling through tech—it’s all another way for me to process and reflect the world around me. And like everything I create, it comes from the same place: honesty, intuition, and a desire to connect.

Would you like to expand on Darlene specifically—maybe a short character bio or logline for her vibe? We could also build a one-sheet or pitch deck-style paragraph if you’re ever looking to introduce her to producers or collaborators.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What part of you has served its purpose and must now be released?
As time passes, I’ve come to see the scope of what I’ve created—decades of photography that has quietly lived in my archives. It’s become clear: this work needs to be released. There’s no reason to hold it back anymore. The pictures speak for themselves. And what they say, I believe, is worth hearing.

Within this body of work are portraits of people who would go on to become icons—artists, performers, cultural figures who later captured the media’s attention. But when I photographed them, they were just part of my world. Friends. Chosen family. People I shared meals and laughter with. People I truly cared about.

I’ve never craved the spotlight. I’ve always seen myself more as the ringmaster—holding space, observing, guiding the energy. Recognition, if it comes, isn’t about ego. It’s about honoring the people I’ve photographed, the moments I’ve preserved, and showing those who know me—friends, family, colleagues—that I’ve always cared. Deeply.

This is not just my story. It’s a visual echo of the lives I’ve lived beside. And now it’s time to let it be seen.

When you were sad or scared as a child, what helped?
I was introduced to the dance floor at a very young age—back when the drinking age was just 18, and I was 15, passing as someone older. The moment I stepped onto that floor, I never looked back. That’s where I truly became a dancer.

Through dance, I learned the rhythm of life. The beat taught me timing. The movement taught me expression. It wasn’t just about performance—it was how I made sense of the world.

While flying through the air, I often thought about my life—my responsibilities, my goals, my challenges. Dance gave me the space to process. To work through things physically, when words or stillness wouldn’t do. There is nothing quite like solving your own problems using your body as the tool. That’s the kind of wisdom the floor gives you—one step, one spin, one leap at a time. Movement truly heals the soul. Learning to break through past trauma with your physical trains your soul .

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. Is the public version of you the real you?
I’ve always been honest. Real. And, as some would say, maybe too real. But I’ve never seen the point in holding back. Considering myself as a truth seeker always led me to an honest life.

Now, with today’s media flooded by exposés and revelations, there seems to be this sudden hunger for the truth. The difference is—I’ve been living in it all along. Telling it like it is. Speaking from experience. That’s always been my language, whether through photography, craft, or conversation.

One of the most valuable lessons I ever received came from my mother. She told me, “Learn how to say it, what to say, and when to say it. And why to say it. “I carry that with me every day. I’ve learned to master not just truth-telling, but timing and tone—because truth without care can be just as damaging as a lie.

What I share—through my images, my work, and my presence—is not filtered or manufactured. It’s lived. It’s felt. It’s real.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. Are you doing what you were born to do—or what you were told to do?
I was one of the lucky ones—a child set free at an early age. I remember being just five years old, walking down the street whistling, when my mother looked at me and said, “You’re happy-go-lucky.” She saw her spirit in me .

That spirit never left me. I’ve spent my life doing exactly what I’ve wanted to do, every single day—with joy. I’ve never felt forced to make money, never been pressured to play a part in order to survive. My path unfolded naturally. And the truth is, it has very little to do with the material world.

I make material things. I create with my hands, my eyes, my heart. But I’ve never been drawn to the marketplace, never felt the urge to chase what’s being sold or promoted or pushed. I never really get. Influenced by commercials Recognition? It’s never been about that. My joy comes from the act of creating, not the act of being seen.

In many ways, I live like a bird—untethered, self-directed. And that freedom? That’s my wealth. It’s a kind of ultra-millionaire status that no bank can measure.

Image Credits
🤳 Robert Desiderio

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