Inside ontheinside.info

You’ve lived in NY for eight years now, did you want to move to the city growing up?
I love the country, I grew up in Texas and North Carolina. But if you’re going to move to a big city, this is the one. There was always a bit of a New York fantasy in my mind. Early in my life, I wanted to be a gallery artist, move to New York, have an artist’s loft and walk around with paint smeared jeans. I was also interested in comedy. And certainly this is the place for that too, you know come here and be a Saturday Night Live writer or have a sketch comedy team.

How did you become a cartoonist?
I was pursuing art and comedy at the same time, but I never thought of putting the two together because I guess I was kind of a snob on both ends I guess. I was living in Boston in ‘98 when I saw this Frontline or Nightline special about the first ever cartoon issue of the New Yorker. I went out and picked up a copy at the newsstand and inside there was a contest form that the New Yorker and the Algonquin Hotel were co-sponsoring. You were supposed to send in your best cartoon idea that had to do with hotels, or hotel life. I spent a few weeks on it and sent some things in. Bob Mankoff, the current cartoon editor at the New Yorker, was the juror of the contest. I was one of the three finalists and got to come down to New York and I met Bob and a couple of the other cartoonists, and I ended up winning the whole thing. So Bob suggested I submit for the magazine. From then on I was doing three cartoon ideas a week and sending them down from Boston. And the third week I sold one, which was just a huge validation. I’d done everything to try to make the rent and to be a comedian and an artist, trying to get in those doors. So to get into a door like the New Yorker, especially something that I’d never intended to do, it really felt like, “ok, this is probably what I am supposed to do”. And so, after you sell your first one you can come down and turn in your ideas in person on Tuesday mornings to the New Yorker. You’re kind of in the club, at least enough to come in on pitch day.

And so you became a New Yorker?
Yes, but I should tell you the bad end of that story. I came down and was doing three ideas a week. You know I’d write a lot of ideas but I’d pick three good ones and pitch them every week. At that point Bob told me ‘you know most cartoonists do about ten a week’. So I started doing fifteen a week because I was wanting to be the young impressive guy. And that whole first year I sold a total of four. It wasn’t a meteoric rise, I definitely had to pay some dues. Each year got a little better, but I wasn’t able to make a living from it for probably four years. And the last four years I’ve been able to. But even now, I mean at the very best, when you turn in your ten, you’re lucky to sell one. So 90% of your stuff gets rejected every week. And that’s top tier, that’s if you’re really hitting, and there’s certainly weeks where you don’t sell any.

That ties right into the books you edited The Rejection Collection, right?
It was an idea I had when I started gathering a pile of rejected cartoons that I still liked. I knew all these other cartoonists who had been doing it for 50 years must also have huge piles of rejects. So I just talked to them and got all their favorites and we’ve done two volumes of The Rejection Collection now (volume 1, volume 2: The Cream of the Crap). Hopefully, we’ll keep going.

What kind of cartoon can we expect in the books?
A lot of the stuff in The Rejection Collection is right for this type of book but very wrong for the New Yorker. To me that adds a level of comedy to it—if you see a joke that’s really sort of tasteless and lowbrow or just stupid, you know the New Yorker’s not going to buy it, but the idea that the cartoonist did it, and actually pitched it to the New Yorker, makes it even funnier to me, like ‘what were they thinking’? These are cartoonists whose work is regularly in the New Yorker, and this is the stuff that they’ve never been able to sell to the magazine over the years. And most of it, yeah, most of it’s outrageous and racy and politcally incorrect.

Also the New Yorker cartoons are famous, but hardly anyone knows the New Yorker cartoonists. So it was a big part of the book for me to share these personalities. In both of the books we have photographs to show you what the cartoonist looks like and then questionnaires about their craft and the way they think. Volume 2 has an appendix about the life of being a cartoonist. A lot of people don’t realize that we’re scraping by, hoping to sell. And that’s my career in a nutshell. I tried a lot of stuff, I’ve been third shift convenience store and done construction and road work, and every other thing. It is the truth that something takes way longer than you think. Like the people who are “overnight successes” you look at it and they’ve been doing it for 10 years in one way or another.

How long does it take to conceptualize a single cartoon?
It varies hugely, sometimes an idea will come to you fully formed, instantaneously while you’re making coffee and you have no idea where it came from. And then other times you just sit there and grind it out and write a lot of really bad ideas and then eventually something comes together. I wish there was an easier way, cause it’s not easy, just sitting there, forcing myself to think of something. For example I’ll start thinking ‘igloos’. Then I go from there to ‘eskimos’ and from ‘eskimos’ to ‘whale blubber’ and maybe there’s a joke about you know some sort of blubber product and then that doesn’t go anywhere so you go back to ‘eskimos’ and say ok, I’ll do an eskimo on a sled and his dogs are, instead of dogs they’re cats. It’s a concept.

Can you take us through the pitching process with the New Yorker?
At the end of each week I take my best ideas and sketch up the best ten, you know, the ten that I can live with. I do that pretty quick, fifteen minutes a sketch probably, maybe less. And then if they buy one I have to do a finished version of it, art-wise. That can take hours, sometimes weeks.

Do the publishers ever send back the finished version?
Not really. You finish it to your liking and you take it in and occasionally they’ll point out something, like the fact checking-department will point out something. The classic is that your buttons are going the wrong way for a men’s shirt or a women’s shirt, or patterns on a bird’s wing are wrong. Their fact-checking department is pretty legendary at the New Yorker, for their articles, but also for the cartoons. But it’s kind of funny because you’re nit-picking about the plumage of a bird not being accurate but ignoring the fact that the bird is talking. Which is also not factually correct.

At what point do you come up with the caption?
That’s the bulk of what I spend my time doing, writing words. I don’t draw anything until I’ve got a good joke or a gag or a concept. It’s word based but there has to be some added element in the visual. Because I had a tendency, coming from a stand up background, to write a one-liner joke and then just draw somebody saying it. Which is not really a pure cartoon, there’s gotta be something in the visual that is essential to get the joke.

Would you say cartoon styles go in and out of fashion over time?
There’s a difference in the drawing style when you look at the old magazines. They were really rich and well-drawn, and today it’s almost better to be ‘badly’ drawn, in a way, it frees up the joke a little more. I tend to draw in an old fashioned way, kind of overly. And sometimes I have to bring it back to keep it funny, otherwise it gets real stale. Like you draw it too well and suddenly it’s not a cartoon, it’s a documentary moment.

But in my work, and in the New Yorker cartoons in general, there’s a dryness to the delivery that typifies them. To me it’s the equivalent of a stand up comedian who does his stuff with a straight face without overselling it with the energy of his delivery. There’s a lot of comedy that is about the momentum that you build in the room. Dane Cook might be a good example of this, it’s more about the energy of him as a performer rather than just the thought behind the joke. He’s almost surfing the audience’s energy, whereas a Steven Wright or somebody, almost lets the energy dissipate in order to focus on the next thought he’s going to give you. Two different things, I personally gravitate to the latter.

Do you perform stand up in the city?
Yeah occasionally. Mostly within the context of speaking as a cartoonist and showing cartoons. But I still occasionally write a random one-liner joke that I can’t fit into a cartoon so I try to tell it on stage.

Do you think New York is a good place to be a cartoonist?
Tremendously. I think what people like about the New Yorker, even if they don’t live here, is that it’s about New York. There’s certainly that element. Because people everywhere used to live here or maybe wished they lived here. So we almost have a responsibility to report in a comedic way what’s going on in New York. And just walking around, you constantly see typical New Yorker set-ups. You know, the hot dog vending cart with a scene taking place, or a homeless guy with a sign, that’s a classic, or even the crazy street prophets, all that stuff. The only thing you don’t see is the desert island, that’s not in New York much.

- interview by Thomas Collardeau, photo by Scott Gordon Bleicher.

See Matthew Diffee’s cartoons at the Cartoon Bank here.