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Rock Art: Jordan Wesolek—Skylines and Summits

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Jordan Wesolek

Climbers love a good view. For Jordan Wesolek, 32, that doesn’t just mean mountains. In his digital piece “A Bit of Both” (above), jagged peaks mirror the Chicago skyline. “I love Chicago,” he says of his current home. “[Yet] if I could be in the mountains all the time, I would as well. I want the best of both worlds.”

That cityscape perhaps struck Wesolek because of its contrast with his tiny hometown, Perryville, Missouri, south of St. Louis. Wesolek grew up in an artistic home: His mom, Juli, was skilled in re-creating photos in pencil sketches and now owns a greeting-card business. In high school, Wesolek played bass in a post-hardcore band. He then studied audio engineering at Greenville University in Illinois, where he started climbing on a small plywood wall at the school’s rec center. When he moved to Chicago in 2011 for a recording-studio internship, the city, he says, was “overwhelming in a great way.” Nine years later, he still calls Chicago home.

Jordan Wesolek

Wesolek has made a living primarily as an instrument technician and camera operator for touring musicians. After college, he toured for four years with the Blue Man Group. During that time, he took up drawing as a creative outlet. When Wesolek realized that realism wasn’t intuitive for him, he instead focused on the minimalist lines and geometric shapes that inform his style today. Now, he crafts dreamy city and outdoor landscapes, with bold lines and deliberate blank space. “It’s just on the verge of reality,” he explains. “I want to create a setting where you understand what’s going on, but you’re subconsciously filling in the blanks, leaving enough for the imagination to fill in.”

Before the pandemic, Wesolek spent long stretches on the road with Bon Jovi, James Taylor, and Drake. On tour, his schedule is packed, so his climbing is often limited to hooking his portable Awesome Woodys Cliff Board to scaffolding under a venue stage. Between gigs, though, he has months off to travel, climb, and sketch. He’s been to beaches and mountains around the world, including to the Philippines, Iceland, and Patagonia—places that have inspired his creations.

Jordan Wesolek

Wesolek also draws inspiration from close to home. Most of his outdoor climbing trips are to the Red River Gorge, whose winding trails and rock amphitheaters feature in his illustrations. Wesolek adds that climbing is a way to build connections wherever he is, whether it’s the local gym in Chicago or a boulderfield in Patagonia. “It builds friendships,” he says. “That’s the accomplishment in itself: I found a group of people I can relate to doing this silly thing.”

When the pandemic struck in March, Wesolek was at an art residency program in Iceland, with plans to work as a camera operator on tour with Justin Bieber, before concerts were called off. Now back in Chicago, he’s rethinking how he makes his living. The usual Chicago summer craft fairs where Wesolek would sell his art are also not happening, so he’s taken to Twitch, where every Tuesday and Thursday he hosts a livestream in which he draws a U.S. state with the state’s bird. He hopes to continue connecting virtually with artists and climbers. “Making art and selling it is great,” he says. “But making that connection with people … that’s the motivation behind this next step.”

About Jordan Wesolek

Courtesy Jordan Wesolek

Home base 


Years climbing


Preferred media

Pen and ink, digital illustration




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