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Mark Montgomery: Caricatures of Bluegrass Legends


Mark Montgomery’s art has done something no one could have imagined. It put Little Roy Lewis, the legendary madcap, frenetic banjo player, at a loss for words.


Lewis studies the details of Montgomery’s pitch-perfect caricature of him: a possum-like grin, unruly white hair, one hand on the banjo, the other stretching his trademark red suspenders. “That’s funny!” Lewis finally declares.


Montgomery’s striking caricatures of bluegrass and country stars such as Bill Monroe, Flatt and Scruggs, and Jimmy Martin--elaborately researched and imaginatively detailed-- speak volumes about their subjects.


“I kind of like being able to wrap up someone's whole life and career into one image,” Montgomery says. “In the back of my mind I want to show respect for these people by doing a picture that can kind of tell their story.”

Montgomery often incorporates “Easter eggs” in his work. It’s a term to describe a hidden message, image, or feature included in a movie, video game, or work of art.

For example, in the background of Montgomery’s portrait of Doc Watson, there are images associated with many of his most loved songs--a Tennessee Stud, John Henry’s hammer, and a shady grove. Montgomery draws Jimmy Martin alongside Pete, his beloved coon dog. There’s a blue moon in the sky behind Bill Monroe. Johnny Cash, his exaggerated hair and eyes making him immediately recognizable, wears a nametag reading “My name is Sue. How do you do?” It’s an homage to one of his great songs.


“I have really loved adding in those Easter eggs into the portraits,” Montgomery explains. “I found so many for Doc Watson in the folk songs he was known for that I created a key that I include with each print. Same for Flatt & Scruggs. The whole idea started with the Bill Monroe portrait and hearing people react and pick out song titles as they looked around the image.”

Montgomery grew up in Northern Missouri in a family that loved art. “My dad’s mom was a schoolteacher, artist, and writer, and his brother and sister are retired art and music teachers,” he says. “My family get-togethers were full of music, laughter, and discussions about art. They were really encouraging and supportive when I would bring artwork to show.”


A high school teacher had been a student of the noted artist Thomas Hart Benton, whose “Sources of Country Music” painting is the centerpiece of the rotunda at the Country Music Hall of Fame. Benton’s layered and richly detailed approach impressed Montgomery.


“I really learned how to tell a story in one picture. And that's what I loved about Thomas Hart Benton. He's one of my favorite artists.”

Though he’s always loved art, his connection to bluegrass music came later, after he moved to Springfield, Mo.


“I didn't know about bluegrass until I came down to college, and right about then, the Oh Brother, Where Art Thou? movie came out.” Around the same time, Montgomery discovered Nickel Creek and was amazed by mandolinist Chris Thile. His wife got him a mandolin, and he began taking lessons from Jeremy Chapman at The Acoustic Shoppe in Springfield. Chapman and his brothers and father, who toured for many years as The Chapmans, have championed Montgomery’s work by displaying it and selling it at The Acoustic Shoppe, which they own. They featured the caricatures in their extensive booth at the 2023 International Bluegrass Music Association convention in Raleigh, N.C.

“They bought a portrait of Bill Monroe I did, and they hung a painting of Steve Martin with his banjo that I did that showed up in the background of their TV show in several episodes,” Montgomery recalls. “I was collecting names of who they thought I should draw next, and I got deeper into this world of bluegrass.”


Montgomery works in various media, including pencil, ink, watercolor, colored pencils, and acrylic paint. Sometimes, he creates caricatures on the computer. But researching his subject is always a crucial step.


“When I start working on a portrait, I sort of go into ‘method actor’ mode. I try to listen to all their music I can find, watch interviews and documentaries and live performances. I don’t use any one photograph to make the portrait but find a recognizable expression and pose and go from there. I watch how their mouth moves if they have an underbite or sneer when they talk. I try to find clues from their life or song titles that I can represent with objects to incorporate into the scene.”

Montgomery is especially excited about the opportunity to design the artwork for Excelsior, a new album by one of today’s great banjo players. “I was able to connect with Alan Munde through The Acoustic Shoppe. A photographer had taken the cover photo, so I used that photo and then kind of worked around it, adding some of the little elements around the text that Alan had given me.”


Montgomery is excited about additional bluegrass projects. He’s created images for singles releases and podcast covers for the Chapmans. And he’s eager to use his talents to help musicians get noticed.


“Every musician I know is so talented, and they work so hard. And I feel like they need graphic support to send them to more audiences. If I can make somebody buy a bluegrass album based on the artwork, then the work is done because once they hear the music, they'll be sold. So that's where I see this going.”

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