Why This Cartoonist Keeps Pitching the New Yorker—Even After 100 Rejections

I first began creating cartoons as a way of communicating with Marta, my wife, when we started dating. I hate texts, so instead, I would draw a cartoon, take a picture, and send it to her. We are both New Yorker readers, and at some point she said that mine were better than most of the the magazine’s. She is not biased. Neither is my mom, also a fan of mine, so I thought it was worth the shot.

I submitted for the first time in the summer of 2016. A former coworker is married to David Sipress, a classic New Yorker cartoonist, and one of my favorites. David kindly offered to take a look at my cartoons. He said that they were totally publishable, and encouraged me to submit to the magazine. He also shared a few pro tips, like that The New Yorker very rarely publishes puns, and when it does, it’s almost always ironically (almost a quarter of the cartoons I sent him were puns).

Almost every week, the New Yorker cartoon editor meets with artists and reviews their work. This meeting is open to anybody. You just show up, sign up, and present your cartoons. So, one hot day in June, I printed my cartoons and showed up at the offices at One World Trade Center, ready to make an impression (good or bad).

The great thing about the cartoon meeting is that you sit with the editor and he gives you feedback, right there. Back then, Bob Mankoff was still the cartoon editor. The opportunity to have a private critique session with somebody like Bob was fantastic. On our first meeting he said that he liked my cartoons, that the drawings were very good, and the jokes were “not bad,” which is quite a compliment coming from him. He picked four of my cartoons and I was thrilled. I thought that I had it made and I was going to start selling cartoons right away.

Not quite. It turns out, the meeting is just the first filter. The editor has a subsequent meeting with David Remnick, The New Yorker’s editor, where he shows him his selection of cartoons for the week. David decides which to keep, but before the magazine buys anything, they will peruse their archives—and cartoons from other major publications—and check that they have not published anything similar first. It’s quite the process. They didn’t buy a cartoon that time. Nor the following week. Nor the next one.

In my meetings with Bob, he was quite blunt, but always funny, and he often built on my cartoons, coming up with new iterations or different ideas for the same joke. The main criticism I received was that my captions were not sharp or punchy enough. That makes sense because English is my second language. In Spanish, I am hilarious.

After many rejections, you might think I’d have gotten discouraged and stopped trying, but I have fun making cartoons. Rejection is just a part of the process that every cartoonist has to endure. It took David Sipress 25 years of submissions until The New Yorker published his work. Bob Mankoff himself sent more than 2,000 cartoons before he sold his first one. However, there are geniuses like Ed Steed who sell after their first submission. He is my favorite. I hate him with every fiber of my soul.

I’m also a bit of a masochist, perhaps as a side effect from attending a Catholic school for 13 years. I am an atheist now, but I still think that the only way to reach salvation is through suffering. I come up with projects that require a high level of commitment, take a painstaking amount of work, and provide low returns. I am very smart.

You can say that there is some sense of pride in a perfect record of 100% cartoon failure—otherwise I wouldn’t put them up with a big red REJECTED stamp on them. But the thing that I am most proud of is that Bob Mankoff said of one of my cartoons that it was the worst he had seen in his entire life. Hell, that’s something to brag about. I said, “Don’t worry, I can do worse,” and he burst out laughing.

However, I am not going to lie. Sometimes it hurts, especially after a few rounds of rejections. But that’s just my ego itching. Who wants to be published in The New Yorker after all? What a bunch of snobs.

That being said, I plan to go back to The New Yorker very soon to meet the new cartoon editor. I might get luckier with her. Getting into the rhythm of drawing ten cartoons every couple of weeks helped me hone my drawing skills, and I’ve missed it since I stopped. The style of the drawings I make for our projects, which often end up in front of clients, is the direct result of those dozens of hours of making cartoons. It’s like illustration gym.

And it’s interesting, the more cartoons you create, the more ideas you generate. At first I was afraid of running dry, but I was surprised when the opposite happened. I have a little red book where I write down ideas for cartoons, and the list keeps growing.

But, most importantly, I just enjoy making cartoons. Sometimes you can see me sitting by myself in a cafe, laughing out loud at my own drawings, which is quite a pitiful scene if you think about it. We are all going to end up as human compost, so we might as well laugh a little on the way to our graves.

Thanks to Lawrence Abrahamson, Michael Hendrix, and Lindsey Rodabaugh for encouragement and help with the exhibit.