Each cartoonist submits up to 10 sketches, so there can be 500 entries competing for approximately 12 spots in the magazine. “On a good week, you might sell one of your batch of 10,” says cartoonist Matt Diffee. “That is 90 percent rejection.”

This is the same problem every creative faces—on steroids: tight deadlines, a crazy competitive environment, a discerning audience, and uncertain pay. If a cartoonist fails to impress, he will miss out on a high three- to low four-figure payday.

So why do they do it? And how do they generate their ideas week after week? Ahead of the new film Very Semi-Serious, New Yorker cartoon editor Bob Mankoff and a handful of contributors share how they dream humorous concepts, even when they don’t feel particularly funny.

How to Come up with a Good Idea

Bob Mankoff describes the cartoon idea generation process as “idea sex.”

“Ideas breed ideas,” he says. “The classic technique is by putting things together that don’t go together,” he says. He begins riffing, offering a potential cartoon setting: heaven. It has clouds, a gate, and Saint Peter. It’s a place people want to get into, but it’s hard to get into. Maybe Mankoff will do heaven as a nightclub with a bouncer? “Or heaven has barbed wire on top to keep out the undocumented angels,” continues Mankoff. “Or there is an easy pass lane into heaven and people are flying through.”

“That’s the basic creative process,” he says. “You float out, What if?”

Mankoff sold his first cartoon to the New Yorker in 1977, became the magazine’s cartoon editor in 1997 and has written his own how-to book for cartoonists, The Naked Cartoonist. He’s always amazed by the people who tell him they have a single great cartoon idea. One idea is never enough, and it’s rarely good. “The way you get good ideas is to get a lot of ideas,” says Mankoff.

Failure is important to the creative process, notes Mankoff. “You learn so much more when you’re doing something wrong and are willing to get that feedback than when you are doing something right,” he explains. “It also teaches you how to be resilient, because you’re going to need that in a competitive, creative enterprise.”

One of Mankoff's early submissions that didn't make the magazine's pages. Used with permissiom from Bob Mankoff. ©BobMankoff

Mankoff submitted “thousands” of cartoons to the New Yorker before it bought his first one. The rejections forced him to think differently about his approach.  “At the beginning, I was trying to do jokes in the vein of established cartoonists and the New Yorker was looking for people with their own voice,” he says. By virtue of doing so many reps, Mankoff developed his unique style.

Given the high rejection rate, why do people pitch cartoons to the New Yorker? “It’s a calling for people because you actually see the world as skewed,” says Mankoff. “That is how I feel about everything. I pretty much go through life joking, not just in cartooning.”

Rethink the Rejects

For Carolita Johnson, a rejected cartoon isn’t a dead cartoon. “I would say that 80 percent of what I’ve sold, I’ve submitted more than once,” she says. “I waited on something I liked and tried it again.” She keeps an ongoing list of half-baked ideas near her unsold cartoons and continuously tries to come up with matches. “I might have a cartoon that I thought looked good at the time, but now looks stupid,” she says. “But let’s try a new drawing and maybe something will come to me.”

In addition to contributing to the New Yorker, Johnson works three different jobs as an illustrator and storyteller. The time crunch motivates her to work fast. “After my drawing started to get better, I decided to stop wasting my time doing roughs and started drawing all of my cartoons on resume paper so they’re ready for sale,” she says. She typically begins with a caption and builds the images around it. Johnson can finish a cartoon in 30 to 60 minutes, though she can’t always guarantee it will be funny.

“I have sold cartoons that I don’t even know why they are funny,” she says. Take the image below. Johnson considered it too morbid. “It’s almost an unconscious thought that I put on paper,” she says. “Something that you don’t say, but sometimes think.” The New Yorker bought it, which emphasizes an important point about creativity and comedy. Being clever is as important as being funny. “It’s about insight rather than searching for a laugh,” says Johnson.  

©Carolita Johnson/The New Yorker Magazine/cartoonbank.com

Competing against the top illustrators in the country for one of the coveted spots in the New Yorker’s pages doesn’t phase Johnson. One might not believe her, were it not for her past experience. “I used to be a model and I had to hand my photos over to people who would smirk back at me,” she says. “Do I think handing in cartoons is hard? Try handing yourself in. I can live with rejected cartoons.”

Grind Your Way into a Creative Zone   

The New Yorker doesn’t have assignment themes, so the cartoonists are able to tickle any whimsy. That kind of freedom doesn’t mean ideas flow more fluidly. “About 95 percent of the time, I’m stuck,” says Matt Diffee. “The idea being blocked is the norm.” To get the juices flowing, he begins his weekly two-hour idea brainstorming sessions with a full pot of coffee and a blank sheet of paper. “As I empty the coffee, I fill up the paper,” he says.

In some ways the process is clinical because he has to ship product every week, regardless of if he feels inspired. “The trick is to not wait for the moments of inspiration, but to be working and let those moments happen while you’re working,” he says.

Diffee’s cartoons are driven by words and ideas that mix surprising elements in a common context—the images come last. To loosen up his concepts, he uses word associations. Diffee’s favorite published New Yorker cartoon (below) began with him wanting to do something on the concept of writer’s block. “I wrote those words down and then thought ‘writer’s block and tackle.’ You could have a bunch of football players trying to block, but that was too wacky for me,” says Diffee. “Or it could be like a horse rider. Rider’s block? That didn’t work.”

©MatthewDiffee/The New Yorker Magazine/cartoonbank.com

He cycled through 40 different concepts over a couple of years. At one point, he began adding words in front of writer’s block—ad writer’s block, business writer’s block—and that led to skywriter’s block. “As soon as I unlocked those words, I knew the drawing had to be an airplane circling in the sky,” he says.  

Each week Diffee generates about 150 concepts that he whittles down to 10 that he is “okay with putting my name on.” “Most of my ideas don’t fully satisfy me,” he admits. “If I have a batch of 10, there will be two that I’m really fond of, two that I’m slightly embarrassed of, and the six in the middle will be fine.” He estimates his success rate over the past 16 years is three percent, but he has parlayed the rejections into a book collection of cartoons that were too dumb, dark, or naughty for The New Yorker.

“We've [New Yorker cartoonists] always wanted to make money off the rejects, and people have tried different schemes as groups and individuals, but apart from the books we haven't figured out a good way,” he says. “New Yorker is still the best gig in town, so the best bet is to try to sell them there eventually.”

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How about you?

What ways do you create ideas on tight deadlines?