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The Mind of a Cartoonist

What does the quirky, obsessive path of Ken Krimstein, a cartoonist for The New Yorker, say about the nature and craft of humor?

Theme: Made in America?


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Ken Krimstein draws about 60 cartoons a week. Every Wednesday he sends 10 to The New Yorker, which begins days of anxious waiting for the cartoon editor's response. Photo by Lori Rotenberk.


  1. The Anatomy of Humor
  2. The Birth of a Cartoonist
  3. How Do You Edit a Cartoon?
  4. A Laugh For $25

Ken Krimstein lives in his head. It’s a mischievous den sometimes ruled by an 8-year-old who is both silly and curmudgeonly and sees life almost in a state of animation. Now 57, and of average size and aspect except for his glasses with ice-blue rims, he was a mere six years old when he felt the giddy rush from drawing something that made his classmates laugh.

And so began a zig-zag life that, on this particular day, has him sketching ideas for me for a gag about themed bedsheets. No, not for kids—for adults, in mid-life crisis. The pattern, he thinks, might be eyeglasses with bifocals, or a days-of-the-week pill box. Or maybe just a martini or highball glass.

“Many of his toons don’t need a caption,” says one magazine editor who uses Krimstein’s work. “The art does the work—and when the caption comes in, the laughter doubles. Bless him.”

Ideas like these appear frequently in such cartoonist bibles as The New Yorker, which recently included some of his work in its “Best Cartoons of 2015.” He’s also been published in The Wall Street Journal and The Harvard Business Review, just to name a few. Although he teaches advertising copywriting at Chicago’s DePaul University by day, he’s driven, almost obsessively he says, to create cartoons.

Absurd humans, petty annoyances, and frequently being just flat-out pissed-off are what fuel his creativity. Those elements, Krimstein says, are shared by cartoonists universally. Everyday life—while riding on the city’s rail line, for instance, he listens for bits of conversation that might anchor a hilarious scene. He constantly observes people at parties, in line for coffee, in stores and on the street, to fill the idea trough from which he feeds.

“My dad just passed away and during the most somber event of my life, part of my brain was picking up gags,” Krimstein recently told me. “I know that sounds morbid,” he confesses, but that wouldn’t surprise anyone who knows him. “Friends came up to me,” he said, “whispering ‘I think you’ll get lots of good ideas out of this.’”

In person, Krimstein, in some odd way, resembles his cartoons. Years hunched over a drawing board have rounded his shoulders. And while his delivery can be slow and deadpan, it’s usually trailed by a grin—on a face that, perhaps not surprisingly, has remained unusually boyish.

“We love Ken’s stuff,” says Tom Jenks, cofounder and editor of Narrative magazine and a former editor at Esquire, Gentlemen’s Quarterly, The Paris Review, and Scribners, who has frequently run Krimstein work. “His cartoons, like all of the best toons, are original and amusing before you ever read the caption—many of his toons don’t need a caption, the art does the work—and when the caption comes in, the laughter doubles. Bless him.”


Some mornings Krimstein wakes up having dreamt of life in a little room in the middle of nowhere, where he can draw and cartoon from morning to night.

I’m standing over Krimstein as he flips through a clip-art book looking for examples of a tudor collar. The collar is for a knight, clad in tights, who is discussing castle design options with a fellow knight, an encounter that Krimstein called “the knights of the kidney-shaped table.” As his figures emerge from the point of his pencil—almost magically it seems—Krimstein giggles. Which he does a lot.

As he pads around in stocking feet in his office—a small loft in his suburban home in Evanston, Ill.—Krimstein tries, as best he can, to explain the mentality that’s drawn to such a quirky profession. “Cartoonists are twisted,” he says. Using himself as an example, he says “I have one foot in reality and the other is, 24/7, in cartoonland. I always have ideas, lots of them, rattling around in my head.” Some mornings he wakes up having dreamt of life in a little room in the middle of nowhere, where he can draw and cartoon from morning to night.

Bob Mankoff, The New Yorker’s esteemed cartoon editor, says the perfect New Yorker cartoon mixes two things that don’t go together—being polite but rude, for example. Overall, Mankoff argues, cartoons are about us. Humor, he once said, needs a target, and our endless foibles are its perfect bulls eye.

Krimstein draws about 60 cartoons a week, and each Wednesday he sends at least 10 to Bob Mankoff, The New Yorker’s esteemed cartoon editor. By the next day, he knows whether The New Yorker will buy any, the long day of waiting causing anxiety and a no-sale making him gloomy. What makes a great cartoon? Timing, he says, and the perfect weight and balance of drawing and words. “A great photo is like one frame from a silent movie, he says. “And a cartoon is like one frame in a comic movie.” This paradigm appears all the time in New Yorker cartoons. The best usually imply a complete story—suggesting scenes, often awkward ones, that occur both before and after the moment captured in the cartoon. While these little portraits may be quick, the notes they strike sometimes run so deep that we enshrine them, turning our refrigerators, Krimstein says, into “cartoon museums.”

In recent months, Krimstein says, there’s been much “tada!” about the cartooning life. The New Yorker has published its giant book, “The 90th Anniversary of The New Yorker Cartoons,” and Mankoff has been making the rounds. At the same time, a full-length documentary, “Very Semi-Serious” by Leah Wolchock, about the genius and art behind New Yorker cartoons, is being featured at film festivals. What is it about these wry creations, and their quirky authors, that draw such delight, admiration, and wonder?

The anatomy of humor, it turns out, is a very serious subject. In 1964, Arthur Koestler attempted to dissect how creativity works in art, science, and humor in a book entitled “The Act of Creation.” Koestler concluded that we laugh when two different frames of reference are set up—“bioassociation” is the term he coined for it—then a collision is engineered between them. Even the 18th century German philosopher Immanuel Kant has weighed in on the topic, with a proposition he called “incongruity theory.” In Kant’s view, jokes happen when people notice a disconnect between their expectations and the actual payoff.

Mankoff, of course, has his own definition of what makes a great gag, an opinion not so dissimilar from those of the great philosophers. In his many talks, Mankoff says the perfect New Yorker cartoon mixes two things that don’t go together—being polite but rude, for example. They might say something about human obsessions, or narcissism. Overall, Mankoff argues, cartoons are about us. Humor, he once said, needs a target, and our endless foibles are its perfect bulls-eye.

Krimstein’s interpretation embraces all of the above, and then some. Cartoonists, in his view, make sense of life. They are devoted to drawings that “puncture authority,” pinpointing the absurdity of the human condition. In the process, they give people a voice for things they feel but can’t say. “Cartoons are often about husband vs. wife, palate vs. disgusting food, waistline vs. belt,” he says. “Gags look at the world the way kids do when they wonder why there isn’t a pill they can take to get through third grade so they can just play. Cartoons are about the weird spaces, our strange thoughts.”

I ask about the metamorphosis of one of his popular New Yorker drawings, of two surgeons about to perform an operation. He says he got to thinking about those “cheapo cheapo [surgical] masks” they always wear. Those thoughts evolved into a cartoon in which one surgeon asks the other, “Guess what face I’m making now.


Can you believe this man is the father of three relatively sane children? Photo by Lori Rotenberk.

Krimstein’s road to cartooning has an odd beginning for a Jewish boy growing up in the 1960s in Deerfield, Illinois. One day, at age six, he decided to draw Santa Claus—somehow managing to render the beard, the big gut, even the patent leather belt. The sketch was such a hit that, from then on, whenever he got noticed it was often to cries of “Ken, draw Santa, draw Santa!” Soon after, he discovered comic books, Mad magazine, and National Lampoon, and was never the same again. It was, to use one of his favorite phrases, Presto-Change-O!

Krimstein devoured each issue of these magazines, which carried subversive and off-color cartoons by guys like Charles Rodriguez, who was drawing gags about the Special Olympics. “When I saw this stuff,” Krimstein says, “it felt like a bolt of electricity going through me. It was like listening to George Carlin or seeing Monty Python for the first time. It was lightning in a bottle and I was a moth to flame. I just couldn’t get enough of it.”

His fate was cemented when he visited his late father at the Chicago offices of Campbell Mithun, where he was the advertising firm’s creative director. Hanging on one art director’s wall was a copy of B. Kliban’s cartoon called “The Birth of Advertising.” “If you’ve not seen it, it’s of a horse shitting men in grey flannel suits out of its ass,” Krimstein says, still amazed. “And I thought, ‘you can actually work at a place where you can put a cartoon on the wall that is hilarious and says your industry is full of shit?’ And that was it. Kliban is still a god to me.”

Drawing cartoons is a tough way to make a living, even though the art form dates back to the Middle Ages, cartone being the Italian word for heavy paper. Top publications pay anywhere from $800 to $1,000 per cartoon, and the average yearly pay is about $25,000. Any cartoonist will tell you that they do it out of passion, and as a way to cast off angst. Krimstein drew them for fun and then later for a campus newspaper, during his years at Grinnell College while he was majoring in history. That led to graduate school at Northwestern University, culminating in a master’s degree in advertising, and then a job as a copywriter in New York with Ogilvy & Mather, a prominent advertising agency.

During that job, Krimstein began experiencing (“this is very true,” he says) “severe cartoon night sweats, obsession, and anxiety.” As he recalls, “I was going crazy during downtime. So I started doodling again. The agency had an abundance of spare paper and pencils. Then I found out that The New Yorker office was only three blocks away. I had to get a cartoon in the magazine, it was all I thought about, and I literally would wake up from dreams, drenched in sweat.” He drew and drew, slipping cartoon after cartoon, following protocol, through the transom. Rejection upon rejection arrived, but that only fed his frenzy.

Over the next decade, Krimstein submitted at least 400 cartoons, never breaking in. This was during the golden era of magazines, and publications such as Cosmopolitan, Good Housekeeping, Playboy, Psychology Today, and Reader’s Digest were all hungry for work. Finally, in the early 1990s, Krimstein landed his first published cartoon, in Good Housekeeping. It depicted an apartment door covered in keylocks. “I was living in my first apartment in New York City and had massive keys I shlepped with me everywhere — this was in the ‘80s!,” Krimstein says. His first cartoon in The New Yorker was published nearly a decade later, in 2000. It featured a New York socialite sitting on a tractor in her toney apartment, with a punch line that said, “I got it on eBay.”


After college, while working at a New York advertising agency, Krimstein found out that The New Yorker office was only three blocks away. “I had to get a cartoon in the magazine,” he recalls. “It was all I thought about, and I literally would wake up from dreams, drenched in sweat.”

It is rare, Krimstein says, that a cartoon fully develops on the first try. Many emerge from doodles that live in one of his many notebooks. When an idea starts to percolate he sometimes revisits the doodle, expanding it into a rough sketch, erasing here and there. Gag lines are often rewritten and edited several times. So, too, with the drawing; Krimstein often adds lines, or whites them out, in order to create “less noise.” Sometimes happy accidents occur with a smudge. An ink wash is a common device for his backgrounds, a style he learned from his father, who was a painter.

Ideas sometimes pop up as he drifts off to sleep, or as he lectures to his class (“I tell the students that I must stop for a second to make an important note when in fact a gag has just come to mind!”). They arise when shopping with his wife, Alex Sinclair, an executive at IBM Interactive Experience, who is often his second pair of eyes in spotting potential gags, or while shuttling his teenage daughter to school. (One of his children—Milo, age 20—aspires to be a cartoonist as well, and recently sparked Internet attention from a cartoon depicting Donald Trump’s hair as a pile of steaming poop.) Notebooks filled with thoughts and sketches lie in stacks throughout the house, mingled with his vast collection of old vinyl records, which range from Miles Davis to The Who to Maurice Chevalier. On the walls hang his passes for umpteen cartoonist gatherings and conventions, along with his first rejection letter from The New Yorker.

One cartoon idea surfaced while scrolling through his email inbox. It was so full of mail he considered unsubscribing from some of his publications; then he imagined two bully cats appearing before a woman at her computer who has just unsubscribed from their publication. He drew them standing before her in a rage saying, “No one unsubscribes from” The cartoon was immediately scooped up by Mankoff.

Krimstein says he never really knows what might tickle Mankoff and he still experiences stabs of trepidation whenever he submits. He remembers the moment years ago, before The New Yorker started publishing him, when he asked a friend to run one of his cartoons past Mankoff, just to get his thoughts. Mankoff’s reply: “Tell him to forget it.” The experience, Krimstein says, “only made me work harder.”

As a cartoon editor, Mankoff’s edits or suggestions are as brief as a gag line. He once told Krimstein that a rejected cartoon was “too European,” which Krimstein took to mean that it depended on an overly heavy-handed, visual pun. When Mankoff likes a cartoon, he responds with a single word: “OK.” “Mankoff is direct and enigmatic,” Krimstein says. “He’s a great cartoonist, yet he is [also] one of us. Cartoonists love to go and hear Mankoff give talks. We listen closely to each of his words, to his speech, trying to pick up pearls of wisdom.”

The tools of Krimstein’s trade are simple—mostly the kind of stuff found in the clutter of a child’s school desk: bristol board, markers, pencils, a chunky gum eraser, White Out, and his favorite of all—rubber cement (“the greatest tool ever!”) because it allows him to quickly slap new gag lines on top of old ones. Pirates are one of his favorite themes—“They have so many cool parts and things that are wrong with them: eyepatch, hooked hand, pegleg, cool cloaks, nasty beards, big earrings, funky hats, gnarly swords, and parrots on their shoulders. What more could you ask for!” He devoted an entire book, “Kvetch as Kvetch Can: Jewish Cartoons” to things he finds annoying about Judaism, which led him to draw a cartoon called “Billy the Kiddush.”


Every two weeks, Krimstein meets Pat Byrnes, a friend and fellow cartoonist who happens to be married to Lisa Madigan, Illinois’ attorney general. One of their favorite meeting spots is the lobby of Chicago’s ornate and historic Palmer House Hotel, where they sit at a table in the shadow of Tiffany torches under a large, French ceiling fresco of figures from Greek mythology. As they work, they attach yellow Post-it notes to each other’s cartoons suggesting possible changes. The suggestions are as simple as changing a word or un-cluttering a drawing, as ambitious as redrawing the cartoon entirely to create more of a punch. Sometimes, after a cartoon is rejected, Krimstein will adjust the drawing or gag line—seeing that it missed the point, or needed simplifying—then resubmit, often with success.

As they work, Krimstein and Byrnes talk about the work of fellow cartoonists, who is publishing where, that cartoons are getting darker in theme, that The New Yorker just ran a cartoon using the word “penis,” and what other words this epic development might allow. Occasionally, they dip into a bit of cartooning history, at one point mentioning that John Updike was a gag cartoonist before he became a novelist. Hugh Hefner drew, too, as did the great James Thurber.

At one point, Byrnes and Krimstein chuckle over the fact that some of their work has landed in The Funny Times, a monthly newspaper that’s popular with a lot of leading cartoonists, but which prints virtually any cartoon submitted. Krimstein confesses to still having an unopened check from Funny Times at home, adding that he really doesn’t want to open it as he knows the contents. “It’s their standard pay, a check for $25,” Krimstein says. “And each time you open one the joke’s on you!”

They speak of tropes: the mafia, a man stranded on a desert island, doctors. Krimstein tells Byrnes he’s had this idea that’s still a notion, and he’d like Byrnes’s thoughts: “There’s this medical team doing an ultrasound on a guy and they are looking at the monitor while the nurse is saying: ‘Should we be concerned that all this shows is The Flying Nun?’”

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