The Willis drawing is front and center. Credit: Andrea Bauer

Joey Gallimore started collecting outsider art by accident. In 2002, when he was around 18, he went to Metro for an Alkaline Trio show and saw a man in the lobby bent over making intricate line drawings. The guy wanted $40 for the one he was working on—a split-city scene featuring a high-rise and Wrigley Field—but Gallimore only had $20 to his name. Eventually, the guy accepted that offer. For a few years, the drawing remained wrapped in plastic in a closet, but as Gallimore got older and more immersed in the local music scene, he realized, holy shit, he’d bought original art from Wesley Willis.

An amateur filmmaker and, to pay the bills, a Groupon employee, Gallimore says he’s always had an affinity for outsider and naive art. “I don’t know if it’s because I’m a comic-book reader or what. There’s something very comic-booky and childlike about the work I’ve been drawn to. Owning it has made me more invested.”

More recently, Gallimore bought an original drawing by Daniel Johnston—it depicts a woman in a bra and underwear kneeling next to a three-eyed alien that sort of resembles his iconic “Hi, how are you” frog—and a painting of a bright-yellow slice of watermelon by outsider art heiress Annie Tolliver (daughter of Mose Tolliver). He doesn’t know how rare either is, considering he purchased the former online and the latter at an estate sale, but he’s an art collector on a budget. Besides outsider art, he’s also acquired “weird random ephemera,” including animation cells from erstwhile Nickelodeon shows Doug and Ren and Stimpy and a prop container of “the stuff” from the 80s horror movie of the same name.

As for what he wants to add to his collection: “I would love to own an original Howard Finster piece. I have a print and would love to replace it with something real.”