Derek Jackson: A Mirror to Culture
Derek Jackson is a self-taught Pop artist based in Harrisonburg, Virginia, whose vibrant works blend bold aesthetics with emotional depth. Working primarily in acrylics, Jackson explores themes of loneliness, nostalgia, and the impact of social media through colorful, layered compositions. His paintings often feature playful 3D talk bubbles that critique the constant commentary of modern life, inviting viewers to look beyond surface impressions. Inspired by the legacy of Pop Art pioneers like Andy Warhol, Jackson sees his work as a contemporary remix—blending the bold aesthetics of the past with the visual language of today’s digital age, from talk bubbles and hashtags to Cricut-cut designs and Photoshop collages.
How did your creative journey begin?
My creative journey began when I was a young child, encouraged by my grandfather. He always supported whatever I was interested in, and when I became drawn to art and drawing, he nurtured that passion. I remember discovering that he loved horses, so I started drawing them just for him. His encouragement made me feel like what I created truly mattered.
I also loved going to art class in elementary school. It was exciting to learn about things like hieroglyphics and then try creating my own versions—those moments made art feel like both an adventure and a form of personal expression.
Over the years, I’ve drifted in and out of art, but the creative spark has never left me. Most recently, my journey was reignited during the COVID-19 pandemic. I found two of the largest canvases I could and felt an overwhelming urge to create something meaningful. After finishing the first piece, I wasn’t sure what to paint on the second—until the idea of the talk bubble came to me. That concept has since grown into a central theme of my work and continues to shape my creative path today.
As a self-taught artist, how have you developed your technical skills over time? Were there specific turning points where you felt your style or voice begin to solidify?
I’ve always been a very self-assessing person. With every painting, I take time to reflect on what I could have done better and where there’s room to grow. I push myself to improve with each piece. Google and YouTube have also been incredible resources—virtual teachers that have helped me develop my skills over the years.
As for my artistic voice, I think it started to take shape pretty early. At first, I was just painting what I thought looked cool—using the symbols and talk bubbles that naturally came to me. Then one day, while sitting in the car, I asked myself a simple but powerful question: What kind of artist am I? The answer came quickly. I thought about the bright, bold colors I love, the fast, expressive way I paint, and the cartoony, graphic style I gravitate toward. That’s when it hit me: I’m a Pop artist.
My style has definitely evolved over time. I’ve explored different types of paintings through the years, but a recent turning point came when I showed some of my prints to strangers and got a lukewarm reaction. Just a simple “cool.” It made me realize that I needed to dig deeper—not just make something visually interesting, but say something with it. That moment pushed me to lean more intentionally into the traditions and concepts of Pop Art, studying the artists who came before me and refining my own approach.
Pop Art has a long history of using bold, commercial imagery. How do you reimagine or remix that legacy through a 21st-century lens, especially with your commentary on social media?
I believe Pop Art is due for a remix—one that honors its roots but speaks directly to the digital, fast-paced world we live in today. Artists like Andy Warhol used the most advanced tools of their time to challenge ideas around mass production, celebrity, and consumer culture. Warhol had “The Factory,” where screen printing and repetition reflected how art and commerce were becoming intertwined. In a similar way, I see it as my role to push those ideas forward using the tools of our time.
Instead of screen printing, I now lean on technology like Cricut machines and Photoshop.. These tools allow for a different kind of mass production—one that's accessible to individual creators. With just a laptop, I can cut precise designs, remix imagery, or generate new visual concepts. It democratized the creative process, and I try to reflect that in my work.
Social media plays a huge role, too. Today’s commercial imagery isn’t just found on billboards or in magazines—it’s in memes, selfies, hashtags, and influencer culture. My work often incorporates talk bubbles and symbols that mimic the way we communicate online. By doing that, I’m blending traditional Pop Art aesthetics with 21st-century language and media.
In my view, Pop Art isn’t stuck in the past—it’s meant to evolve with the culture it critiques. My art reflects how we live now: constantly scrolling, reacting, and performing. I want to capture that energy, remix it, and make people think about what we’re really consuming—and what it’s saying about us.
What does a typical day in the studio look like for you, and how has your art practice grown or changed?
My schedule is a bit unconventional—I work full-time at Michaels and also work as a realtor, so I don’t get to spend as much time in the studio as I’d like. But whenever I do have a free moment, especially in the evenings, I head down to my basement studio to paint. That space becomes my escape—a place where I can focus completely on creating.
My process usually starts when I get excited about an idea. That spark can come at any time, even during the workday. Once I have the concept, I move into planning mode—using Photoshop to sketch it out and experiment visually before committing it to canvas. I try to find the most efficient way to bring the idea to life, both in terms of time and materials. That often means blending traditional painting with tools like Cricut or digital design.
Over time, my art practice has become more intentional and streamlined. When I first started, I painted more impulsively. Now I think more strategically—I design the composition digitally, plan my materials, and aim for a balance between spontaneity and structure. Even though time is limited, I’ve learned how to make it count. Every studio session is focused, purposeful, and driven by the excitement of bringing a concept to life.
Nostalgia plays a key role in your paintings. What are some memories, cultural moments, or visual icons you find yourself returning to again and again?
Nostalgia definitely plays a role in my work. I often use the iconography of old-fashioned technology—things like rotary phones, VHS tapes, or bulky TVs—as a way to communicate memory, emotion, and the passage of time. These objects carry a certain weight because they remind people of a different era, one that feels more tactile and less digital. I like using them to contrast our current world, where everything feels fast and disposable.
One personal example is my eyeglass painting. I found an old pair of glasses that belonged to a friend who had moved away. Painting them became a way to hold on to that connection, to preserve a moment that felt important. It wasn’t just about the object—it was about what it represented: memory, absence, and hope. In a way, painting those glasses felt like saying, "You can come back now."
I’m drawn to moments and visuals that spark a personal or collective sense of “remember when?” Whether it’s through everyday objects or emotional symbolism, I use nostalgia not just to look backward, but to reframe the present through a sentimental, human lens.
How has social media impacted your work?
Social media was actually the first major inspiration for my work. I became fascinated by how something that started as a way to share family photos has evolved into this massive force that shapes how we think, communicate, and see the world. Platforms like Facebook, Instagram, and TikTok are no longer just about connection—they’re about performance, influence, and competing ideas. That shift is central to my work.
I often explore how social media impacts the way we see ourselves and others, especially as artists. It sometimes feels like we aren’t considered “successful” unless we have a certain number of likes or followers. That pressure can distort the value of the work itself. It becomes less about the art, and more about how it's received—and who is watching.
I also think about how opinions on social media can cloud or even cover up the art itself. For example, we often check reviews or comments before watching a movie or listening to music. We’re influenced before we even experience the thing for ourselves. In my paintings, I play with this idea by using talk bubbles, comments, and symbols that mimic the noise of social media—suggesting that all this chatter can sometimes drown out the original message.
Social media is also becoming a new theme in my upcoming work. I’m currently creating pieces that deal directly with how these platforms have changed us as people—how we present ourselves, how we argue, how we crave validation. It's not just a tool anymore; it's part of our identity. And I want my work to hold a mirror up to that.
Do you see your work as a mirror to culture, a challenge to it, or something else entirely?
I see my work as a mirror to culture—specifically, the way we communicate and present ourselves in the digital age. Every talk bubble in my paintings represents the endless stream of comments, opinions, and reactions we see online. It’s like capturing a screenshot of our collective voices, where everyone is talking, but not always listening.
I’m not trying to directly challenge culture in an aggressive way, but I do want to reflect it back at people and make them pause. There’s humor in what I do, but also a layer of truth. The only real “challenge” I set is for people to be kinder, funnier, and more thoughtful in their responses—because honestly, I need better material for my next painting!
So in a way, my work is both a mirror and a conversation starter. It shows where we are, and it quietly asks, Is this how we want to keep showing up?