Orlando folk artist Jon Napoles hangs his phantasmagorical windows on walls for an exhibition at d.b.a.

“I’m not joking with you, dude. You cannot achieve this look, this transparency, this color on anything but glass. I wish you could, it’s such a nightmare to make these things. … I can’t tell you how many stitches and cuts I’ve had from broken glass and razor blades.”

Central Florida artist Jon Napoles has an easygoing, almost 1960s psychedelic-hipster speaking voice and he knows his way around a yarn — even when he’s talking about injuries suffered from his rather unique creative practice. It’s disarming and charming alike, and belies both his prolific output and otherworldly artistic visions.

Napoles paints almost nightly, a healthy byproduct of lifelong insomnia, putting fantastical and abstract creatures and landscapes on panes of glass, former house windows. But he’s unhurried about putting his work out there. He’s not stressed about exposure, eschewing social media, and lets the run of happy accidents and personal connections that led him to art in the first place roll on.

It’s like this: Napoles began making his unique and eccentric art over a decade ago, when a job doing renovation work pointed him toward the reclaimed household windowpanes on which Napoles paints his florid and rough-hewn renderings of his dreams and visions.

The dreamworlds depicted in this show at d.b.a. — his first exhibition in 2025, which runs through early September — are populated with birds and horses.

“I had this recurring dream where I had transformed into a bird, so that somehow manifested into the set of paintings,” says Napoles. “I don’t sleep. I’m a medical insomniac, and so I’ll have these, like, weird, rutted dreams. They kind of worm their way in. And I try to figure out, what does it mean?”

Napoles had just finished the 10 horse paintings that would become Horses That Fly when he stopped in to the Mills Avenue bar recently for a quick whisky. The folks who run the joint happen to be longtime collectors of his work and casually asked if he’d be interested in exhibiting there. Napoles casually answered in the affirmative.

Napoles started painting just as casually, to help his brother Pete with something to hang on the walls of his bar so it could qualify as a gallery and skate around code enforcement. He used what he had on hand, windows from old houses encountered on a renovating job, and set to work.

It hasn’t always been ethereal visions of horses. Napoles — fittingly for someone who first “exhibited” in a bar — partly made his name early on painting tallboy beers, Warhol soup-can style, in ever-stranger fashions.

“I used to paint tallboy beer cans, and these weird cat-headed figures. Back in the day, I didn’t take it very serious. I would just do tallboys for tallboys,” remembers Napoles. “People still like them. There’ll be days where I have, like, a really elaborate razor-cut still life of flowers and people are like, ‘That’s great. I’d like to buy a tallboy painting.’ That’s fine. You know, the hits,” says Napoles.

Crucial early supporters include folks associated with Stardust Video and Coffee, who invited him to take the leap and set up shop at their eccentric Grandma Party holiday bazaar. “My very first year I made $400 and I was like, ‘Wow, this is great, man,'” marvels Napoles. “Last year, I made like, $15 grand in like 30 minutes, but I still think about how excited I was that first time. … I bought me and my pals tickets to go see the Breeders in Atlanta.”

Napoles was soon selling paintings out of his car. “We would just roll up to places, like the Highwaymen,” says Napoles. “Like, ‘Yo. You want some paintings? We got paintings in the trunk.'” Galleries would come calling, including Orlando Museum of Art, where he exhibited in 2019.

He’s a lot more serious about his craft now, but approaches it with the same anarchic fever of the early days. He isn’t particularly precious about holding on to his paintings. He tells OW he only keeps one painting at a time for himself and the rest he’s happy to sell and give away, finding more joy in the frenzied process of creation over the final product.

“I have a huge room set up because I’m painting on glass in reverse, which is the worst, man. It would be impossible to do one painting at a time because it takes so long to dry,” explains Napoles. “You gotta let it dry, cut it back, light it, reverse it. So what I’ll do is I’ll set my whole room up with multiple paintings, and I’ll put my mock-ups above them on the wall, and I just go to it. Sometimes you catch the spark, man, and you run with it.”

And the frames of his paintings — the actual frames from these windows’ past lives — are sometimes as storied and unique as the art they encircle. These particular frames, says Napoles, came to him via a friend in Mount Dora, and some will be used for his next series — landscapes. More connections, more happy accidents.

“I don’t mess with the frames, I don’t treat them. I think that’s a big draw for my paintings. You have this slick, colorful painting, and then you have the rough, jagged juxtaposition of this historic frame, both of these textures side by side,” says Napoles.

Napoles treats showings in bars exactly the same as he would a formal gallery; there’s no hierarchy. Indeed, he seems to relish the freedom of exhibiting in bars and unconventional spaces. But Grandma Party, in particular, holds a special place in his heart — and he approaches it as both a homecoming and an everything-must-go purge. (Just don’t tell the museums.)

“At the end of every year, I pull all my paintings, whether they’re from my shows or galleries, and I sell them like Black Friday, 50 percent off at Grandma Party. Because that’s where I started,” says Napoles. “I could care less if I sell a single painting at this show, I’m just tickled to show art. I want someone to see what I did before I get rid of it. I’ve had an exhibition at Orlando Museum of Art and I put just as much effort and joy into a bar as I do a museum. I’m like Nicolas Cage. I give it my all, no matter the role.”

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This article appears in Aug 6-12, 2025.