Artist Spotlight: Greg “CRAOLA” Simkins Brings Surreal Vision to Richmond

This October, the Richmond Tattoo & Arts Convention welcomes a true icon of contemporary surrealism: Greg “CRAOLA” Simkins. From gallery walls to graffiti-covered drains, Simkins has built a decades-long career blending fantasy, fine art, and street culture into unmistakable narratives. This year, he joins us in two powerful ways: creating original work for our Live Art for Charity event benefiting Studio Two Three, and leading an intimate workshop at the Richmond Tattoo & Arts Academy.

We caught up with Greg ahead of his Richmond debut to talk about his artistic journey, influences, and what attendees can expect from his time at the show.

When did you first start creating art, and what inspired you to start?
I began drawing pretty early on, probably around age 3. Like a lot of kids, my mom sat me down in front of cartoons with some crayons and butcher paper, but unlike most, I never stopped. It might have been the comics, the cartoons, or maybe just boredom, but I kept going. Even when other kids stopped drawing, I found new friends who shared the same drive, and we pushed each other to keep creating.

You began your journey as a graffiti artist. How did that experience shape your current style and approach as a surrealist painter?
I started graffiti around 1992 during a pretty introverted phase. Drawing was my comfort zone, but after a teacher told me I’d never be a real artist, I stopped sharing my work. That changed when a classmate showed me Subway Art. I was hooked. I started painting in LA’s sewer drains with friends, copying the characters I’d been sketching in my blackbooks. It became a lifestyle focused on style, community, and technique.

Eventually, those characters, comics, and influences from Juxtapoz, Heavy Metal, and Renaissance masters merged into my acrylic paintings. I moved into galleries, worked on video games like Spider-Man 2, and spent over two decades building a career across graffiti, fine art, and storytelling. None of that would have happened if I hadn’t picked up that spray can.

When did art evolve from a passion into a full-time career for you?
Right after graduating from college, I was waiting tables and doing freelance design when friends from my graffiti crew told me JNCO Jeans needed an illustrator. I applied and got the job. I’ve been a full-time artist ever since.

How would you describe your artistic style to someone experiencing your work for the first time?
Maybe Salvador Dali meets Disney. Or Saturday morning cartoons meets the old masters. There’s a lot of discovery and wonder.

Your pieces blend classical painting, pop culture, and storytelling in such a unique way. What themes or ideas do you find yourself returning to again and again?
I’m always coming back to the hero’s journey. It’s the framework for so many stories I loved as a kid. I created a world called The Outside, and everything I paint exists there. I’ve written pages about it, mostly for myself to keep track of its logic and characters.

Have you attended the Richmond Tattoo & Arts Convention before?
This will actually be my first time in Richmond. I’ve heard great things and I’m really looking forward to it.

You’re teaching at this year’s Academy. What can attendees expect from your class?
I’ll be painting live throughout the weekend and sharing techniques with anyone who wants to watch. I’ll also be giving a talk and slideshow covering my journey, the ups and downs of being a working artist, and how I approach world-building.

The convention is full of top-tier talent. Are there any artists this year you’re personally excited to see or connect with?
Too many to name. But I’m especially excited to reconnect with my longtime friends Gunnar and Jesse Smith. Can’t wait to hang out and have some laughs.

Your work has caught the attention of collectors around the world, from Hollywood icons to art enthusiasts. How do you stay grounded and inspired with such a global following?
Honestly, I don’t think about it too much. I just love painting and expanding The Outside. At the end of the day, I’m still that introverted nerd obsessed with drawing.

Do you have any upcoming projects, gallery shows, collaborations, or product drops you can share with our readers?
I’ve got several group shows, limited edition drops, and collaborations coming up. You can find updates at GregSimkinsArt.com

For emerging artists or tattooers attending your class or stopping by your booth, what’s one piece of advice you’d give about building an artistic identity?
Get as many eyes on your work as possible. Use every tool available to share what you do and let the work speak for itself. That’s how you grow.

Want to learn from legends like CRAOLA?
Sign up for a session at the Richmond Tattoo & Arts Academy. We have special ticket options for artists that include parking passes, convention passes, and other VIP perks. See them all here.

Planning to stay for the full weekend? Don’t forget to book your hotel early on our website for the best rates and availability.