Bob Mankoff, the former cartoon editor at The New Yorker, on starting a new career

During his 20-year tenure at The New Yorker, iconic cartoonist Bob Mankoff published a whopping 950 cartoons and reviewed thousands of submissions.

Mankoff is about to launch Cartoon Collections, a new website which will house Mankoff pieces and material from famed sources including The New Yorker, Esquire, Playboy Magazine, National Lampoon and many more.

Mankoff spoke with Ladders about his next big move and adding humor to your day.

Done not done

Mankoff said “At this point, most people in the field of humor and cartoons know what I’ve done but not all of them know that I’m far from done. I was cartoon editor of The New Yorker for twenty years and a cartoonist there for twice that long. That was a really nice run in which among other things I founded The New Yorker Cartoon Bank and invented The New Yorker Caption Contest. Nice laurels to rest on but I’m a restless guy with a laurel allergy, so, among other things, I left The New Yorker to become cartoon and humor editor of Esquire, co-founded an AI humor company as well as a new cartoon licensing business”

The same but different

When asked about his new launch, Mankoff said “My new venture is very similar to in structure (they both seek to license cartoons in all kinds of media), but differs in a number of ways. The first, and most important perhaps is that works and doesn’t. That’s a harsh statement but true. It’s almost impossible to license a cartoon on because of cost-cutting and a revolving door of execs who had no feel for cartoon humor and how to monetize it. Quite simply I’ve created in the first place to do right what is doing wrong. And then do it better than it ever did by adding collections of cartoons beyond that of The New Yorker such as Esquire and The National Lampoon. We’re starting off with around 20,000 cartoons and a year from now should have over six-hundred thousand on every conceivable subject for every conceivable use.”

Funny you should mention it (but not to HR)

“First off, humor doesn’t have to be edgy to be funny,” Mankoff said. “We often confuse shock and the excitement it causes with funniness. Edgy humor is humor that makes us feel uncomfortable in some way akin to embarrassment. Same thing with offensive humor. When we’re embarrassed we laugh. When we laugh we often retroactively assign funniness to anything that made us do that. So, not always, but often, we don’t laugh because something is funny but rather we think it’s funny because we laugh. That said, I’m not against humor being offensive because humor is part of free speech. There is no objective standard for going too far. In fact, no one can even give a good definition of what going too far is.

In the workplace, the best rule of thumb is not to joke about anything that HR doesn’t think is funny and HR doesn’t think anything is funny.”

Be more playful to be funny (even at work)

“You cannot teach anyone to be a comedian anymore than you can teach anyone to be a professional tennis player,” Mankoff said. “But you can teach anyone to play tennis and you can help anyone learn to have a playful attitude that will lead them to be amusing in social situations with friends and colleagues. It doesn’t take much to make someone laugh in a conversation, especially someone you know. In fact, most laughter occurs naturally in informal conversations and the humor required for it is very minimal.”

Humor works at work

I told Mankoff I’d once read that humorists are the greatest masochists on earth since they earn a living hoping that other people will laugh at their work (paraphrasing. it was actually mostly about stand-up comedians). Mankoff replied, “That seems sort of like a joke that misses the point. The laughter in that instance is not ridicule but praise. They’re not laughing at your work or at you but with you and your humor. If the audience doesn’t laugh as a comedian, you’ve failed.

The point is made is this joke:

“Everyone laughed when I said I was going to be a comedian. They’re not laughing now.”

Well if you’re a professional humorist, one thing that should motivate you, since this is your profession, is money. Always get paid. But if that’s the only thing that motivates you, you’re a hack. It’s important to me that other people appreciate my humor but it’s more important to me that I do.”

Lessons in being pithy and to the point

If you’re trying to add humor to your work, take note “In terms of writing a joke, with the exception of shaggy dog stories, the shorter the better. You can do that by editing to make shorter or better with tweaks.

“Everyone laughed when I said I was going to be a comedian. They’re not laughing now.”

Is made better by substituting “They” for “Everyone” at the start of the joke above.

“They laughed when I said I was going to be a comedian. They’re not laughing now.”

Also, in being funny you need the element of surprise so the punch line should always be at the end. For example is this cartoon of mine

The word “jail” is the punch. The caption would not work as well if it were

“Now, you’re going to have to go to jail for this over here”

One more thing: Mankoff suggests you “Check out And, if you’re not 100% satisfied with it, try 75%. That usually works for me.”