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

Local Woman Vows To Stay Off Internet Because of ‘The Last Jedi’

DENVER, CO – Lauren, 26, is fed up with hearing about the latest Star Wars film, The Last Jedi, and it hasn’t even come out yet.

“I’m tired of seeing the countdowns and the speculations – this has been going on since October. I’m just ready for it to end.”

Lauren thought she’d be OK by the time Friday, December 15th rolled in but she was caught off guard by last night’s world premiere.

“I was minding my own business on Twitter, getting my usual Saturday night dose of quality cat videos when I was blindsided by the Star Wars premiere.”

She almost threw her phone out the window of her apartment when she saw a tweet with potential spoilers. Lauren has since logged out of all social media profiles and is considering never signing back in, even after seeing the film.

Lauren also refused to comment on whether or not she thinks Porgs are going to be the next Jar Jar Binks.

Writing Jokes with Taylor Bryant

Hey, we went to school together! How have you been since graduation?

Hey, we did! Fuck, it’s weird that we’ve been out of school longer than we’ve been in school at this point. Anyway, I’ve been good! I feel like this is a loaded question. Good as of late because I have a job I love and a life I’m molding into something that I love. Ask me this a couple of years ago, though, and my answer would be very…different. Not bad, just different.

Would you change anything about how you navigated college?

Hmm, I don’t think so. Maybe paid better attention in Spanish class because I should absolutely be bilingual at this point? I do often wonder why I didn’t consider going somewhere warmer for school. Or even abroad! But, overall, I think different things happen for different reasons. You know, destiny and all that. I do wish I visited Canada. That’s something that didn’t even cross my mind while I was there.


Me too— and the Niagara Falls we’re right there. How did you end up working for NYLON?

The short version: My boss now was my colleague while I was at Refinery29. We kept in touch when she left and, one day, a gig opened up for the web editor position and she reached out. I guess I was also qualified.

What’s involved in your day-to-day there?

I’m kind of the overseer of news. So, every morning, I’m in charge of assigning the first news stories of the day and sending out a digest, which basically includes a rundown of what people are talking about on the interweb. Then, I make sure that we’re jumping on those more timely/on-brand stories throughout the day.


You know when people say everyday’s different? I always thought that was a cop out, but it’s really not. I write two news stories everyday, so that’s consistent, and I’ll either conduct interviews for upcoming stories, work on a feature story, go to a press preview, edit some stories; it really depends. There’s also a lot of tedious email answering and internet browsing thrown in there.

I don’t want to get too in the weeds, but how do you actually go about structuring a story?

Oh! Well, I suppose it first starts with an idea. Then, that will dictate what kind of story it’s going to be — a feature, personal essay, review, interview q+a, etc. Let’s talk feature. I tend to start with doing a shit ton of research, which helps me figure out what direction I want to go in. Then, you do interviews if interviews are necessary. Then, you somehow manage to pull it all together and make something of quality out of it. I don’t know, this the point where I usually blackout.

“Future was gracious enough to fly us home on his private jet. Who says chivalry is dead??”

What kind of things did you do at Refinery29?

I started out as the beauty assistant there, so I did a lot of assisting, writing, some complaining, helped with social media at one point, a lot of beauty product testing, some photo things. I eventually graduated to beauty news editor where I basically did the same things, minus the assisting and double the writing.

What’s the best part about your job now?

I will be forever indebted to the beauty space because going that route is what allowed me to become part of the media world, but my favorite part about my job, now, is that I get to write about basically anything (music, art, fashion, politics). I’m not an expert in everything by any means, but I think that’s a good thing. It allows me to challenge myself creatively and stretch my writing capabilities.

What advice would you give someone who wants to do what you do?

This is always a weird question because I don’t feel like I am in anyway qualified to give out advice. But I’m going to pass along advice that someone once told me which is to take every single interview you’re offered, even if you’re not interested in the job. You don’t know what might come out of it. 83% of the jobs you get are going to be through someone you know or meet. So, go out and meet people. And try not to burn bridges with people. If that doesn’t work, forget I said anything.

Any thoughts on that Pepsi ad?

Wouldn’t have happened if Obama was in office. Kidding. It was incredibly tone deaf and is a prime example of what happens when few to zero people of color work at these bigger companies. Or, when few to zero people are listening to the opinions of people of color at these bigger companies.

What makes something funny?

I guess it varies by person, but I think how much you can relate to something is key. For something online, the choice of meme is essential. In person, the delivery.

What do you want to do next?

This…is an interesting question that I’ve actually been thinking about a lot. I’m not sure, career wise, but I do know that I want to travel. Like, quit my job for a couple of years travel, not that two weeks mess. And/or, move to a new city. This is all hypothetical though so, boss, if you’re reading this, please don’t hold it against me.


 Taylor is a web editor . She doesn’t take life too seriously.

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

Writing with Sowmya Krishnamurthy

What’s the toughest part about being a music journalist?

Hip-hop journalism — like all aspects of the music industry — is dominated by men. For women, there’s a constant fight to attain credibility from artists and the industry as a whole. You want to be respected for your pen game. That often means you just have to kick down the door for a seat at the table.

How can publishers be more helpful to freelance writers?

Pay me (and on time!) That sounds pretty basic but you won’t imagine how many publishers believe the adage of ‘paying your dues’ really means working for free. I’m of the mentality that: you get what you pay for. Publishers that value quality journalists get the best work while other outlets rely on interns to write cover stories.

There’s also a larger trend across media of ‘pivoting to video’ that gives me pause. It’s essentially a nice way of saying that a publication is going to fire writers in lieu of YouTube stars. Yes, video is an integral part of media but it isn’t the only piece. I wish more publishers would play to their strengths and be thoughtful in their strategy versus jumping on the clickbait flavor-of-the-week.

Gosh, I know exactly what you mean. I was at a place that pivoted to video three years in a row. When you are interviewing someone, what’s the best way to get them to open up?

Listen. I can’t tell you how many journalists try to make the interview about themselves. Shut the fuck up and listen.You just might learn something.

What’s been the most underrated album of the year?

Action Bronson Blue Chips 7000. If you’re a fan of crazy, weirdo hip-hop sampling, you should listen to this record. Harry Fraud, Alchemist and PartySupplies handle production. Like, cmon bro. People slept on that album.

How has Twitter influenced your career in journalism?

Twitter is a game-changer for me. I can’t tell you the number of gigs I’ve booked because of my social media presence. Nearly every editor (as well as radio and TV producer) I’ve worked with initially connected with me on Twitter. For journalists, it’s a great platform to build your brand and network.

Queen Latifah recently spoke about how consciousness in rap is changing. Do you agree? If so, why might it be evolving?

This battle between consciousness and whatever the opposite of that is — Soundcloud trap at the moment (?) — has been going on forever. Some of the biggest artists of the genre, from Kendrick Lamar to J. Cole, are definitely more conscious but there’s plenty of the converse as well. It’s perhaps more balanced than in recent time; but “money, cash, hoes” rap isn’t going anywhere.

What do you think rap will sound like in 10 years?

Whatever music people listen to on Mars. Earth is pretty much fucked amid our current political climate and well, the climate. I’ll be on Mars streaming sound-waves through my retina.

What makes you laugh?

Classic episodes of The Simpsons. I’m a total nerd. I can pretty much run dialogue line-for-line from seasons 1–9 and I watch all the commentaries. If you’re a Simpsons fan and don’t have the FXX streaming app: Stop reading this interview and get it. I’d probably be some combination of Lisa Simpson, Milhouse and Poochie the Dog.

Why do writers beome writers?

I’ve always believed that I have important shit to say. I had my own column in my hometown newspaper (The Kalamazoo Gazette), and my college paper (The Michigan Daily). In hip-hop, I have a unique perspective that no one else has. Seriously, how many Indian rap journalists do you know? I love being able to use my voice. Plus, seeing my byline is still pretty cool.


Check out Sowmya Krishnamurthy at http://www.thesowmyalife.com/ and on Twitter at @SowmyaK