Dubuque Artist Twists History & Art

Iowa Culture
Iowa Arts Council
Published in
4 min readNov 10, 2022

In a stained-glass studio in Dubuque, the artist Tim Olson is assembling a new body of work — arms, legs, mustache and all. The puzzle pieces form a glowing Gothic portrait of Dan Gable, Iowa’s patron saint of wrestling.

The idea came from a fan’s suggestion that Olson initially brushed off.

“I thought it was such a weird idea because when I was growing up, [Gable] was like Iowa royalty,” he said.

Tim Olson, making a stained-glass portrait of Dan Gable.

Most of Olson’s portrait subjects are more ordinary than Olympian, but he’s not one to dismiss a weird idea. In his latest series, the 2022 Iowa Artist Fellow paints modern-day Iowans in the formal style of the Northern Renaissance, led by Flemish artists like Pieter Breugel and Jan van Eyck. In Olson’s folk-art take, sullen 4-H kids appear in arched panels like the authors of the four Gospels. The Nativity plays out in a trailer-park triptych.

Tim Olson’s oil painting “Four Win at State Fair.”

He appreciates the contrast between fine art and pop culture, like the “funny, sad and slightly creepy” artwork in a book he discovered years ago, called “Thrift Store Paintings.” He likes a good mashup — and the actual process of mashing things up.

Is it “Cartoon-Expressionism? Naïve-Academic? Picturesque-Messiness?” he wondered. “Maybe all of the above.”

Olson grew up in Marathon, near Storm Lake, and graduated from Laurens-Marathon in a class of 60. He studied photography and painting at Bemidji State University, the University of Iowa and Loras College in Dubuque before jumping into a 20-year career as a photo-studio printer in Los Angeles and Chicago.

“Self-Portrait with Senior Portrait.”

When he and his wife, Christine, decided to leave suburban Chicago, they chose Dubuque, where he had studied and she had often visited for her work with the National Trust for Historic Preservation.

“She took to it right away,” Olson said. “It took me a few years to get a feel for the place.”

But the more he learned about Iowa’s oldest city, the more he saw it as a place for artistic inspiration. His painting studio is upstairs at the Key City Creative Center, in what was once the haymow of an old livery.

Several years ago, he was drawn to some old photos in one of his wife’s history books, “Dubuque on the Mississippi,” by William Wilke, and eventually teamed up with Dubuque historian Mike Gibson to exhibit and publish an extensive photo collection of local shops, factories and offices from 1912. The project, “A City at Work,” won an award from the State Historical Society of Iowa and inspired Olson to photograph a similar series a century later, in 2012. (Coincidentally, Olson was born halfway in between, in 1962.)

“A City at Work” led to other photography projects, including a series of portraits and interviews in the neighborhood around St. Mary’s Church (now Steeple Square) and a 110-foot panoramic portrait of 600 people at DubuqueFest in 2013. He created another panoramic portrait at the Iowa State Fair three years later and has featured some of its characters in his recent paintings.

A segment of Tim Olson’s “Iowa State Fair Panorama” from 2016.

With the recent fellowship from the Iowa Arts Council, Olson plans to explore his old stomping grounds in northwest Iowa. He plans to roam Buena Vista and Clay counties to see what has and hasn’t changed and then document his observations — as history, art or a mashup of both.

“When I make a painting or a project, it’s something I’d like to see myself,” he said. “You hope there’s enough other people out there who are going to be interested in the same thing.”

When he finishes his stained-glass portrait of Dan Gable, he’d like to invite other Iowa artists to create additional portraits in glass. He envisions a statewide traveling exhibit, sort of a chapel of notable Iowans.

There’s no shortage of inspiration, weird or otherwise.

“I always have more ideas than I could ever finish,” he said.

Gothic Dan, a work in progress.

Michael Morain, Iowa Department of Cultural Affairs



Iowa Culture
Iowa Arts Council

The Iowa Department of Cultural Affairs empowers Iowa to build and sustain culturally vibrant communities by connecting Iowans to resources. iowaculture.gov