We recently had the chance to connect with Jimmy Houston and have shared our conversation below.
Jimmy, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What’s the most surprising thing you’ve learned about your customers?
What’s surprised me most over the years is how deeply people connect with my art—especially the retro animation characters. At the end of the day, most of us are just big kids. I’ve seen buttoned-up adults completely drop their guard when they see my work. Sometimes it’s just for a second, but other times, something really hits home—they see a part of themselves or something they’ve been missing.
One of my favorite stories goes back to when I was just starting out and still working a day job. A friend of mine hated his construction job, and over burgers one afternoon, he said, “I’m going back to school to become a doctor.” I told him I was going to pursue art full-time. That moment, he said, “When I have my own practice, I’m commissioning you.” Ten years later, he actually called me up—he’d made it—and he kept his word.
The piece I created for him was called The Clinic. (The piece included below with all the cartoon med students). It was packed with detail, humor, and meaning—monkeys, tin men, tough cartoon girls—all woven into this surreal tribute to his journey. It was more than a painting; it was proof that chasing your dreams isn’t just for kids.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name’s Jimmy Houston—born and raised in Houston, Texas. I’m a fine artist who paints retro-inspired animation, filled with characters of my own design: cartoon monkeys, tin men, tough girls, and all kinds of misfits. I work with a lot of mixed media. In an age of AI and digital everything, working with all these layers feels grounding—there’s something powerful about building texture with your hands, creating art that you can feel, that’s imperfect, and human.
I’ve been blessed enough to pursue this career for over a decade now, and it’s been incredible to see how these quirky characters have connected with people. Not everyone “gets” my work, but for those who do, it tends to land deep. I’ve found that cartoons can speak to really universal themes—people often see themselves in these characters, and that’s powerful.
What keeps things exciting is that I’m always evolving—always learning, experimenting, trying new ways to communicate ideas through color, texture, storytelling, and world-building. Lately, I’ve been expanding that world into merch—shirts, mugs, hats, stickers. It’s wild to think someone might start their day sipping coffee from a Rig the Monkey mug. That kind of connection means a lot.
Right now, I’m working on two big commissioned series, and what I love about that process is getting to know the clients on a deeper level. We collaborate to create something that’s not just personal—it becomes part of their everyday space. There’s something sacred about painting a piece that hangs in someone’s home. I never take that for granted.
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 breaks the bonds between people—and what restores them?
Whether it’s in art, personal life, or just being human—relationships are at the core. A question like this goes beyond career and really speaks to character. For me, it all comes down to trust—built through integrity, communication, and knowing who’s truly in your corner when things get tough.
An art career can be a rollercoaster—feast or famine—and it definitely puts those relationships to the test. I’ve had people lift me up in big ways, and I’ve also felt let down when I needed support the most. But trust is also what rebuilds those broken connections, even though it takes time.
At the end of the day, life is about having the right people around you. My art, even in its fun and playful style, is just another way of communicating that. When someone works with me—when they work with Jimmy Houston—I want them to feel that integrity. I want them to walk away with something meaningful, high quality, and uniquely theirs. I always go the extra mile to make sure of it. And beyond the work itself, I’m always looking for that genuine human connection—that shared experience that makes it all matter.
What fear has held you back the most in your life?
That’s a deep question, and it really hits something beyond just my art career—it gets to the root of how I operate as a person. Fear can be a real beast. Making a living as an artist is like walking a tightrope, and the fear that’s tripped me up the most is people-pleasing. There’s this old, deep-rooted lie that says love is earned through performance, and I’ve had to work hard to unlearn that.
As I’ve grown in my craft, I’ve realized I can’t afford to play it safe. Avoiding risk only leads to creative stagnation, and that’s not where good art lives. The art life keeps you moving, thinking, adapting—and that’s helped me grow personally, too.
Fear has no place in the studio. When I sit down at the canvas, I can’t be thinking, “Will people like this?” I have to create from a place of inspiration and truth—make the work first, then figure out what to do with it. Because if fear gets into the process, it shows. It bleeds into the brushstrokes, and the piece loses its spark.
On my best days, I push past that fear. On the tough days, it’s right there knocking. The key is to name it and deal with it. For me, the antidote has always been faith—faith in my Creator and in the calling I believe I’ve been given. That’s what keeps me steady through both the highs and the lows.
Sure, so let’s go deeper into your values and how you think. Is the public version of you the real you?
People always ask me, “Is Jimmy Houston your real name or just your artist name?” And I tell them—Jimmy Houston was my name long before I was an artist. (And yeah, I am related to Sam Houston.)
But it’s a good question, because it touches on something deeper—about identity. The truth is, I try to be the same person whether I’m on the phone with a client, in the studio, at home, or playing with my kid. It’s a journey, though. Like anyone else, I’ve worn a professional mask at times. But when it comes to making art, that mask has to come off. Art is too raw for anything fake.
A lot of people see a smoking monkey with an eyepatch and think it’s just for laughs—and it is fun—but there’s usually something deeper behind it. Something personal, social, or even spiritual that’s woven into the work. So when I talk about my art, I can’t help but keep it real. The act of painting—and sharing that process—keeps me honest. It keeps me vulnerable.
At the end of the day, I hope that when people meet me outside of my art, they see the same person they hear in my work. The people I respect most in life are the ones who are genuine wherever they are, and that’s something I strive for too.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. When do you feel most at peace?
Wow, we’ve really gone deep—fear, peace, trust… some big topics today. When it comes to peace, that’s something I’ve had to learn to seek out intentionally, especially in this kind of work. The art career, like any entrepreneurial path, can feel like a nonstop race. There’s always another idea to chase, another project to launch. And with that can come a scarcity mindset—wondering when the next feast or famine cycle will hit.
That constant drive can be energizing, but if it’s not kept in check, burnout shows up fast. So I think it’s crucial—not just for creatives, but for all of us—to learn how to slow down, to find some kind of peace in the middle of it all. Because if we don’t, the work—and our well-being—start to suffer.
For me, I feel the most peace when I’m sketching purely for the joy of it. No pressure, no expectations, just drawing like a kid again. In that flow state, everything else fades away. I’m not worried about outcomes—I’m simply doing what I was made to do. That space is honest. It’s full of joy and presence, and if I can carry that energy into a finished piece, it’s always more real and meaningful.
I also find peace in nature—just stepping away and taking in the world God created. As someone who makes things for a living, it’s humbling and grounding to witness what He’s made. There’s something sacred in that, and it reminds me to slow down, breathe, and just be. The hard part is, I don’t do it often enough. But peace like that doesn’t just happen—you have to seek it out, you have to choose it.
Contact Info:
- Website: https://jimmyhoustonart.com/
- Instagram: https://www.instagram.com/jimmyhoustonart/
- Facebook: https://www.facebook.com/jimmyhoustonart
- Youtube: https://www.youtube.com/@JimmyHoustonArt/videos?app=desktop
Image Credits
Jimmy Houston
