Writing Jokes with Matt Diffee

What first attracted you to single panel cartoons?

I was always interested in drawing and comedy. The comedians I gravitated towards were the cerebral one-liner types like Steven Wright, Mitch Helberg, Emo Philips. I like the simplicity and precision of that style and the fact that it’s a little more about the thought and writing behind the joke than it is about the performance of the joke. Single panel cartoons, especially at the New Yorker seem to be the cartooning equivalent of that. Very much about the idea of the joke, the literary aspect and the drawings don’t over-act.

How might stand-up comedy compare with cartooning?

Stand up is easier and harder. It’s easier in that you can develop a character and rhythm that the audience can get onboard with. A cartoon has to do all the work right there on the page one-on-one without any introduction or warm up. But standup’s harder in that you have to do a second job alongside your joke-telling job and that is reacting and controlling the room and surfing the crowd’s energy. And of course you have to stand up there and personally experience those bombing moments. Cartoonists are anonymous.
What do you do when you’re having a tough time coming up with ideas?

That’s the usual state. I always feel like I have absolutely nothing and will never think of anything funny ever again until the moment when I suddenly do. One of my favorite quotes about creativity is by Edwin Land: “Creativity is the sudden cessation of stupidity.” So when I’m in that stupid phase (which is always) I’m just trying to get the gears going with anything I can. I’ll try to come up with my own writing prompts or flip through some sort of resource material. Just to get something to react to, a jumping off point. I try to resist the temptation to let myself off the hook by telling myself “Oh I need to get up and take a walk” or “I think a cookie would really help me think better.” I try to just keep plugging away. I can’t say that I always succeed at that. Sometimes I’ll just go outside or take a hot shower or do something to get myself in the comedy frame of mind like look at old cartoons or watch ten minutes of random standup. It’s actually better for me to look at bad comedy than stuff I think is great.

When did you realize you got good at cartooning?

A couple years into doing it probably, but that was after twenty years of doing art and at least ten of doing comedy in various forms, mostly just learning about joke writing. My first hurdle in cartooning was to learn to let the picture do half the work, either the setup or the punch line or part of both. I had a tendency at first to just write odd one-liners then draw odd people saying them and that’s not really a pure cartoon. It can work, but in the best cartoons, the caption and the image are insufficient by themselves. The idea needs both. Unless it’s a wordless cartoon, which is nice when you can pull it off.
“I’m starting to really like the smell of cocaine.”
How has The New Yorker influenced your career?

It’s proved to be a good spot for my sensibilities. Even though I grew up a country boy in Texas, I came to love whatever it is you would call the New Yorkery style of humor. I was reading SJ Perleman in college. It’s not a complete match. I do some stuff that doesn’t suit the New Yorker but I’d say it’s an 85% match. I didn’t have to adapt what I do to fit in there. I was able to do my thing and develop a voice that is parallel to the magazine’s. And of course I’ve gotten better rubbing shoulders with my amazing colleagues there.

Why don’t we have more cartoon publications these days?

Good question. I have no idea. A lot of cartooning is now on the internet but that came after other magazines had already stopped running them. Maybe we’re in a golden age of web comics, unless that’s already over. The golden age of magazine cartooning was long gone by the time I started. One good place that’s still publishing a lot of cartoons is The American Bystander which is a really great independent humor magazine. It’s crowd-funded so your readers should go check that out and pitch in.

This was a part of Matt’s If Cowboys Were Smaller series for The Believer magazine.
What’s the weirdest idea you’ve ever had for an illustration?

That’s interesting. I don’t think of my stuff as weird. Absurd maybe but I’m always going for laughs so to me the absurdity has to have an element of sense to it. I’ve drawn talking animals and aliens and grim reapers but those are hardly weird in the cartoon world. I once drew a pine tree driving a car that has a human-shaped air freshener hanging from the mirror. Is that weird? And a two-headed kid with glasses complaining to his mom that kids at school call him “eight eyes.” And a long-torsoed cat called a wiener cat. Maybe I do draw weird stuff.

What do you think people don’t realize about your job?

Most people think of cartooning as drawing. It’s actually way more about the thinking and the writing than it is about the art. The drawing part is just the end zone dance.

Why do you think cartoonists become cartoonists?

Probably lots of reasons. For me, I wanted to do comedy in some form or another and I have a lot more confidence in my drawing ability than my personality or performance skills. Generally I think cartoonists like doing something that’s entirely within their control. It’s very pure and personal. They like to perfect something before presenting it to others. They secretly want people to think they’re brilliant and they want to make hundreds of dollars a year.

Check out Matt’s book, “Hand Drawn Jokes for Smart Attractive People” on Amazon & pick up a free art print after signing up for his newsletter at www.mattdiffee.com

Writing Jokes with Charlie Hankin

Can you describe your general process for creating cartoons?

My cartoons start as one-sentence descriptions I write in my notebook. I’ll sit down at a cafe or go for a long walk and just let my mind wander. I know I have a potential cartoon when: 1) I’ve constructed a joke (say, a sperm realtor talking to two sperm house hunters in front of an available ovum, saying “It’s perfect for starting a family.”); and 2) I can visualize the picture that goes with it (the “for sale” sign out front, a little tie and clipboard for the sperm realtor). Some cartoonists just start with a blank sheet of paper and doodle until they arrive at a picture that becomes their cartoon. I’ve never worked that way — I think writing a joke out verbally, in longhand, is a better way for me to be sure that the thing actually is a proper joke, as opposed to something whimsical, charming, associational, et cetera… all words that are nice but don’t include “funny.”

Once I have a collection of jokes, I’ll sit down and draw them all out at once. It usually takes me all day to draw sketches of 10 new cartoons, and another day to draw cleaned-up versions. I used to work entirely in traditional media, but now I work with a digital tablet and Photoshop.

When The New Yorker buys a cartoon for publication, I will redraw it at top quality using conventional tools — India ink on watercolor paper with a wash.

What makes for a good work space?

Quiet, with access to caffeine. Coffeeshops are good for writing as long as there are no distractions. I can’t write while listening to music or podcasts. When it comes time to draw, I binge on podcasts. The Best Show with Tom Scharpling is a huge help. So are Hollywood HandbookI Seem Fun: The Diary of Jen Kirkman, Stop Podcasting YourselfMisandry with Marcia and Rae, Pistol Shrimps Radio, the list goes on…

How did Good Cop Great Cop first get started?

Good Cop Great Cop is my comedy duo with Matt Porter. We started as an independent web series in 2011, basically out of a shared desire to have some sort of regular output. We were making a video a week for a long time.

The web series is on a temporary hiatus now, but only accidentally — we have other projects in development, and can’t make a new sketch as often as we’d like.

How did you prepare to play Marco on I Love Dick?

I Love Dick was a total whirlwind. They cast the supporting roles in the series pretty rapidly, so I found out I had the part the same day I flew to LA for it. The next day, Jill Soloway ran a workshop with her acting guru to get the cast up to speed. She has a strong philosophy in place about how the beats within a season or episode motivate key transitional moments called “beat changes.” These in turn motivate things like blocking. It was fascinating. The day after the workshop, I got fitted for wardrobe and my beard prosthesis, and two days after that was my first shoot day.

Wow, that’s bang-bang! I’m glad it worked out. As for cartoons, is there anything you especially like to draw?

Here’s a total non-answer: anything that makes me laugh out loud once I’ve drawn it. It’s rare, but it happens — a certain expression on a character’s face, a totally insane environment to set a cartoon in.

What’s the hardest part about cartooning?

Starting with a blank page every single time. It never gets easier to fill that page.

What makes a cartoon funny?

I think a funny cartoon must be funny both in content and form. On the most basic mechanical level, a cartoon should have a legible, almost text-like joke. I’m not talking about the words in a caption; the best captionless cartoons are text-like. You “read” the image of a cartoon from left to right, top to bottom, and your eye is attracted to continents of black ink.

A funny cartoon sets up an incongruity somewhere near the top left quadrant, and draws the reader towards a resolution near the lower right. This sets up a naturalness to the cartoon that makes it gettable and transparent; readers don’t know they’ve been manipulated, and the mechanics of the manipulation feel invisible.

But mechanics aside, I think a funny cartoon is drawn funny. Some people are so naturally gifted at this it hurts — Sam Gross and Jules Feiffer come to mind. It’s always been a challenge for me to loosen up the way they do, so I tend to mine understatement and restraint for a sort of deadpan alternative. But the best cartoons work at both levels: they entail the mechanical delivery of a funny idea (content) and they do it with a drawing that is itself funny in a vacuum (form).


Check out Charlie’s work on Instagram at @mecharliehankin and in Conde Nast store here: https://condenaststore.com/art/charlie-hankin