Into the Darkness - David Stoupakis

Published: 29 March, 2012 - Featured in Skin Deep 210, April, 2012

For centuries, adversity has lead to the creation of captivating works of art and, yes, even success. New York-based painter and tattoo collector, David Stoupakis, is the latest in a line of greats who’s turning his hardships into gorgeous tableaus.

Born in Brighton, Massachusetts, Stoupakis was faced with his first major challenge the moment he was born. As a premature baby, he had to overcome a number of complications early on in life, including a learning disability that would end up pushing him towards artistic expression.  

It was during his first year of school that teachers realized Stoupakis’ creativity held the potential to develop greatly, a fact that his parents immediately embraced.  
“I always just knew that making art in some way or another was what I was going to do with my life. It was the one thing I felt I was good at, and I was lucky enough to have the support of my family. I had a really shitty time in school. I grew up with a learning disability, so I had to go to all these special schools. It sucked, but when my parents saw my interest in art, they really got behind it. I will always be so grateful to my mom and dad for all the encouragement they gave me.

“My early influences came from Walt Disney movies, TV cartoons and the comic books I read,” says Stoupakis of his beginnings. “Making art as a kid was always a great escape for me. I would like to say the first thing I ever drew was something cool like a skull, but it was more likely tracing my hand to make a turkey for Thanksgiving at school. Drawing skulls, devils and pentagrams came later down the road,” he laughs.

Although the imagery of those early days didn’t include anything exceptionally dark, it was still considered gloomy enough by many of Stoupakis’ instructors to be a cause for concern. But even with all the parent-teacher meetings and discussions, none of it seemed to rub off with age and today Stoupakis creates paintings that often feature dark skies, mischievous creatures and blood.

“I understand and see why maybe some people would feel that way, but I have never seen the work I do as dark. I look at it more like I am painting my interpretation of what I see as the human condition in the Land of Oz,” he explains.

Enrolling in the Art Institute of Boston in 1992, it took Stoupakis a year to realize that art school wasn’t for him. “I learned a hell of a lot in the time I was there, but I just really couldn't hang with the artsy fartsy kind of vibe that was going on there at the time.” Which meant it was time to become a self-taught artist.  

Selling his first painting in 1995, Stoupakis recalls, “it was the best feeling in the world and still is today. There is nothing like creating something for yourself, something you truly believe in, and then finding out it moves someone else enough that they want to own it.”

Following a stint as an artist for a gaming company, Stoupakis chose to focus all of his time and talents on painting in 1999, which also happened to be the year he met his muse, Aprella.

“Aprella has had so much influence on my work, not only as my muse, but she has always been the voice I go to to get an honest opinion on something I am working on at the time. Aprella has been here for the evolution of my work, so she got to see the good with the bad and has a very good understanding of what I am trying to say with my work, so she is great for me to bounce ideas off of.”

Nowadays, Stoupakis calls New York City home and as he puts it, it was an inevitable move. “As much as I love being from Boston and going back to visit, it’s a very conservative city and there wasn’t much room for the kind of work I was doing, so I always knew I would end up in NYC where there was more opportunity. This city keeps you on your toes.”

His devotion to the craft, combined with his indisputable talent have resulted in ever-increasing praise and popularity, and as it turns out, success has forced Stoupakis to slightly alter his artistic process.

“As of late, I would say the ideas for the paintings are very planned out and executed before I paint them. I do a lot of sketches and color studies. The paintings I do take me quite a bit of time and I am always working with some kind of deadline these days, so I never really have the time to make lots of changes and have the paintings grow in that kind of way.”

When it comes to art, Stoupakis also takes time to appreciate the work of others, including that of tattoo artists, being an avid collector of ink himself.

“I was 18 years old when I got my first tattoo and I couldn’t wait to get it. Back in 1992 it still wasn’t legal to get tattooed in Massachusetts, so my friends and I would all drive up to New Hampshire to get tattooed at this shop. I can’t remember the guy’s name, but I got this terrible dragon tattoo that looks like a salamander with wings,” he laughs. “But I still love it today.” 

Since then, Stoupakis has gotten work from Joshua Glantz, Paul Booth and Vincent Castiglia. “Booth and Castiglia both have very unique styles; you know when you see a Booth or Castiglia tattoo. There is something very special about them – it’s true art.

“The biggest piece I have right now is a whole sleeve that was all laid out in one sitting so the piece would work together as one. The sleeve is [made up] of parts of paintings of mine that have different significances in my life. I am having my whole back tattooed as we speak. The back tattoo is of this big beautiful, creepy tree that is a tribute to my big brother, Alex.”

Asked what he thinks of those who still refuse to consider tattooing a true, legitimate art form – we all know those people, unfortunately, do still exist – Stoupakis thinks it’s rather simple.

“They need to open their eyes. I don’t see any line between it, it’s all art to me. If I didn’t have paper or canvas, I would find something else to put my creativity on. It’s about what comes through you, not whether it’s on skin or hanging in some gallery.”  

So would he ever consider becoming a tattoo artist? After all, there’s likely no shortage of tattoo lovers who would line up to have a piece of work as unique and captivating as those created by Stoupakis adorning their skin.

“Yeah, I definitely have thought about doing tattoos before, but I haven’t been at the point yet where I felt like I would be able to give the learning of it 100 percent, and I have always felt like if I can’t give it my all, then it would just be disrespectful to the art of it.”

Seems like Stoupakis won’t be trading in his brushes for a tattoo machine in the near future, so art appreciators will just have to settle for enjoying his work on canvas. And when they do, they should set out to discover what David Stoupakis hopes is present in every one of his paintings: “Question, beauty, and hopefulness.”


Stoupakis’ muse and partner, Aprella, truly does do it all. Actress, model and all-around artist, Aprella has walked the runways at LA Fashion Week and during the Cannes Film Festival, has done Halloween performances for both Alice Cooper and Heidi Klum, and has been featured in films and music videos. Aprella is the definition of versatility, so is it any wonder she’s the perfect artist’s muse?

The Girl Who Sat For Too Long

“That painting was created for a show called In the Nursery. It’s a painting about procrastination, not letting the world pass you by,” says Stoupakis of his latest limited edition, hand-signed giclee print, which just so happens to be available in his online store now. With only 50 copies up for grabs, you better hurry if you want to snag one of these gorgeous pieces for yourself. You know you do!


Text: Barbara Pavone; Photography: David Stoupakis