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How’d A Cartoonist Sell His First Drawing? It Only Took 610 Tries

This story came from a listener of the NPR program series, My Big Break, about career triumphs big and small, hosted by ARUN RATH.

Tom Toro in Kansas City. He’s a cartoonist at the New Yorker. It’s a career he kind of stumbled upon. He actually went to film school at NYU. That’s when he realized he was in the wrong field. At the time, Toro had no idea what he was going to do.

TOM TORO: Up to my neck in debt, directionless, feeling lost in a huge city, and I went into a pretty dark depression. I ended up dropping out of film school. I floundered around for a little while. And I finally just had to come back home.

I had sort of been a golden child. I was valedictorian of my high school class. I went to Yale. I got into NYU right out of undergrad. And all the sudden, I’m back at home. I don’t think my parents really understood what I was doing there. And I almost didn’t understand myself. So that first period of being at home was just kind of long, quiet dinners, sitting around the dinner table, trying to make conversation. I went to this used book sale, and in a cardboard box, there was a stack of old magazines. For some reason, I was drawn toward them. And I started rifling through them. And they were just a bunch of old New Yorkers. And, you know, there they were – these cartoons, in among the articles. I don’t know. Something just clicked. And I just – I started drawing again.

Here’s the thing about breaking into the New Yorker. No one tells you how to do it. So I just sent them to the New Yorker by post. I would walk from my parents’ house down to the post office and mail off these packets of cartoons that I was sketching together every week. You know, I kept getting those form rejections back. It’s, like, two of the most elegantly phrased sentences. The New Yorker found the way to, like, most courteously and most briefly reject people. It’s just beautiful. You feel, like, so honored to receive it. And yet it’s a brush-off. It’s so well done. But I just had a stack of those.

And finally, I decided, after about a year-and-a-half, I’m just going to go and meet the guy – the editor, Bob Mankoff – and sit across from him and show him my stuff and see what he has to say. And, you know, I went in. He looked at my stuff. You know, I was just, you know, nervously sitting there, waiting for him to say something. And I remember he just – he looked up and he said, you know, I don’t see any joy in these. These aren’t ready yet. And you’re, like, OK, there’s – I see the standard here. I know that I have to live up to this, you know. And so I went back home. And I just threw everything that I had done previously out the door, sat down with a blank sheet of paper and just tried to draw from the heart.

It was a perfectly ordinary day. I was just back in the backyard, and I wandered back into my mom’s office – went in there, logged in. And there, sitting at the top of my inbox, was the email from Bob’s assistant. It said cartoon sold.

So that was my big break. January 20, 2010 – cartoon sold (laughter). It was the 610th cartoon that I sent in to them. Two cowboys sitting at the bar – in the background, you see the saloon doors. Over the top of the saloon doors, there’s the face of a third cowboy. But below the saloon doors, it’s just blank. And one of the cowboys at the bar is pointing back over, and he says, that there is one bowlegged cowboy.

xo, jan