Kevin O’Malley Might Just Be The Most Prolific Illustrator You’ve Never Heard Of

Even now he’s often at odds with his editors. They are always trying to get him to end on a “jump up idea”—a lesson. “But I try to write things that amuse me. Mostly I want funny.”

The second of six kids, O’Malley grew up outside of Philadelphia, in a rural area he calls Pennsyltucky, with Chevy Novas sitting up on blocks awaiting transmission repairs. One of his earliest memories is watching a Charlie Chaplin movie with his dad and two of his siblings, one still in a highchair at the time, and his dad being concerned that the kids didn’t find it funny.

“They don’t have senses of humor,” he bemoaned to O’Malley’s mother. That was when O’Malley first realized that humor was a gift, something that was important in his family, and even as a young boy he liked how he felt when he made someone laugh. He could often convey that with his art, as well.

“My parents saw that I liked to draw—but I was never the best,” he says. Math also wasn’t a strength: “I got 960 on the SATs—720 was in English and I can’t figure out the remainder,” he jokes. “I’m not the sharpest tool. I admit it freely.” O’Malley is quick with such self-deprecating remarks and it’s sometimes difficult to discern if it’s a bit or something that goes deeper.

Despite what he thought, O’Malley got into every art school he applied to and arrived at the Maryland Institute College of Art in 1979. It was a big change from his small, sheltered hometown and O’Malley started to really see the world for the first time.

“Art school is great for opening your eyes. I got better at listening, too,” he says. While at MICA, he also met his wife, Dara, who works as a jewelry designer. “Never marry an artist,” he says with a chuckle. “Marry an accountant so they can take care of you. Don’t marry another artist.”

Ever since high school O’Malley had been religiously submitting book proposals to publishers and he continued to do so during his time at MICA. But with no bites and desperate to pay off a loan to his parents, he took a job with The Becker Group, creating what’s formally known as Santa Reception Areas—or holiday displays—at malls, and hotels, and on cruise ships. “It kind of takes all the charm out of Christmas,” he says. “I would add yellow to the snow in the mall—now it looks realistic.”


Despite his submissions, he didn’t get published until he was in his late 20s. “I was rejected at least 100 times. I kept all the letters—’thank you but no’ and ‘while I really appreciate your work, I’m afraid it’s not for us.’” The motivation behind keeping all the rejects? “I kept the letters because I was bitter and vindictive. I had hoped to meet [one of the rejectors] one day and have the letter folded into a paper airplane with a sharp point and throw it at their forehead.” (You can see why kids love him.)

Luckily, Andy Stewart, the former Mr. Martha Stewart, of the Stewart, Tabori & Chang publishing house, liked O’Malley’s interpretation of the well-known folk song “Froggy Went A-courtin’” by Tex Ritter.

“He published it because he used to sing it when he went to college,” remembers O’Malley. “I said, ‘What the hell college did you go to?’ He said, ‘You’re a brazen man, Mr. O’Malley, but I’m going to publish your book.’”

That was 1992 and it remains O’Malley’s only book that’s been banned by Baltimore County Public Schools. It wasn’t a huge surprise, since Froggy robs a bank, evades the law, and spends much of the book drinking and smoking.

The following year, he followed that work with a wordless picture book called The Box, about a cardboard box that rockets a small boy and his teddy bear into space and back again. Next came Bruno You’re Late for School, about a rhinoceros, O’Malley’s favorite animal, trying to track down his homework. And he hasn’t stopped since—though the time may be coming.

“I don’t know honestly whether I want to continue making books,” admits O’Malley. “I thought I’d get to 100 books, but it’s just a number. Most of my books are out of print. Most are Third World fuel. They’ve been laminated into Ikea coffee tables.”

Nearly all are O’Malley’s words and drawings, but there’s still something electrifying about collaboration. “The thrill of someone else’s manuscript is the possibility of the interpretation,” he says. Because of this, O’Malley changes his art style on just about every book he’s done. “My agent said, ‘If you keep changing, no one knows who you are.’ I said, ‘I don’t care. I bore easily.’”

But his agent isn’t wrong—it can be hard to pinpoint his style. “I have boxes and boxes of colored pencils. I use them on a lot of things. But [sometimes] I don’t feel like using colored pencils…I feel like watercolor. Or I feel like this one is acrylic paint or this one is oil paint. Or this one is done with the computer. It feeds the mania of creating art.”

But it might also explain why O’Malley is the most prolific illustrator most people have never heard of. The artist remains unfazed. One of his most popular books, Once Upon a Cool Motorcycle Dude, tells the story of a boy and a girl working through different ideas of how their fairy tale should evolve. O’Malley insisted that the publisher, HarperCollins, should use three different illustrators for the project to reflect the different viewpoints (the kids and the two separate fairy tales). And when Nickelodeon bought the rights to the book, they agreed to do multiple illustrated styles as well. He’s proud of the finished product.

O’Malley reads the book out loud, looking at the pages, although it’s clear he knows the words by heart. It reads like a conversation between two real children. “That was a wonderful book to do because we gave them honest talk. We didn’t play down to them,” he says.

And while he might not want to admit to overt sentimentality, O’Malley loves the idea of ​​families reading his books together. “My greatest disappointment is that I never got cameras mounted in people’s homes so I can see them reading my books on the couch. There is nothing to me more terrific than curling up with a kid and reading a book. Make it cozy, and then you start reading, and then you stop and talk. It’s just so lovely to do that.”

“He’s a child in old man’s clothing,” says Fred Rasmussen, The Baltimore Sun obituary writer who has been a friend of O’Malley’s for decades. “His personality is just irresistible,” says Rasmussen. The two are part of a large crowd that meets regularly at Zen West in north Baltimore. The group often includes retired teachers, editors, and even former governor Martin O’Malley (no relation to Kevin).

“Kevin has a curious habit—a vodka tonic with 19 limes stuck in it,” says Rasmussen, who always teases his friend: “Are you afraid of scurvy? We have drugs for that.” The two men banter, trying to make each other laugh. “He’s very, very funny. He always says the same thing—’find joy’—when he leaves. He brings great joy to people.”

That’s partly because of O’Malley’s ability to hold onto much of the wonderment many of us lose as adults, though he deadpans that his own two sons have “never been an inspiration.”

So maybe it’s just other kids that inspire him. School visits are his fuel. “I must have been three books in when I realized there were such things as visiting authors,” he says. He started going to elementary schools and not just reading his books but really educating kids in how to tell a story.

“The fun part is watching parents laugh, teachers laugh,” he says. “The kids are easy. You say ‘fart’ and you get them.”

After the readings, kids usually mob O’Malley like a rock star, sometimes literally climbing all over him. One time he caught a teacher shaking her head at him, amused. “Stand up,” she whispered conspiratorially. “Keep the germs below the waist.” He never forgot that.

“That’s some sage advice. The nose-picking crowd is out there glomming on me. But they’re nice. Kids are nice. And they attempt to be funny and work out humor.”

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