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Esquire humor editor Bob Mankoff launches a site that he hopes will be the main destination for cartoons

by Bob Mankoff / The New Yorker (by Bob Mankoff / The New Yorker)

NEARLY THREE decades ago, Bob Mankoff hit upon the idea of launching a revenue-generating website of rejected gag cartoons, and by the end of the ‘90s, his successful Cartoon Bank website was reportedly receiving 100,000 hits a day.

Mankoff sold that business to the New Yorker in 1997 — the same year he became the magazine’s cartoon editor. Now that he is the humor editor at Esquire, Mankoff has a vision for a much bigger site.

This month, the veteran editor and cartoonist launched as a way to spotlight and monetize thousands of works published in the New Yorker, Esquire, National Lampoon, Playboy and Barrons.

Cartoon Collections will also curate from the half-million works from the library of the recently acquired

Mankoff says he is drawing upon years of hard-won lessons to try to create a destination site as part of a larger licensing business.

“The market for cartoons is large but widespread and dispersed,” Mankoff tells The Washington Post’s Comic Riffs. “It needs a central place where anyone who needs one for any purpose can find what they need.

“Cartoon Collections will be that place,” he adds, “as it aggregates cartoons as Getty or Corbis aggregates photos.”

Crucial to his mission has been getting established cartoonists to sign on, and he’s landed nearly 100 so far. “I have a track record at the Cartoon Bank for making money for them,” he says, “and treating them and their work with the care and respect they deserve.”

Mankoff says the cornerstone for such a site is the simple unique appeal of a well-crafted gag cartoon.

“We understand that cartoons, especially single-panel gag cartoons, can communicate a thought as perhaps no other medium can,” he says, “and be remembered because the message comes with the sweet elixir of humor.”

Mankoff has seen the magazine market for freelance cartoonists shrink significantly since he entered the business as a cartoonist in the ‘70s. Yet he believes a cartoon aggregation site, through innovation and experimentation, should be able to generate millions of dollars in annual revenue — while maintaining a 50/50 split “with the cartoonists no matter where their material has been published, after our costs.”

Mankoff says his site is also featuring a caption contest — an idea he brings over from his New Yorker days. The new contest, though, may gain twists in technology — reflecting Mankoff’s self-described “wonky” fascination with how “humor is judged, evaluated and created.”

“I’m once again engaging Rob Nowak and his team from the University of Wisconsin to develop crowdsourcing algorithms to help judge the contest,” Mankoff says. “Over time, I want these to become more sophisticated and take into account not only a funniness rating, but an originality one as well.

“Another project,” he adds, “is developing an AI tool to help you write a great caption.” (He’s also a part of Botnik Studios, a company that uses AI to generate other kinds of humor.)

Mankoff, who edited the new treasury “The New Yorker Encyclopedia of Cartoons,” says that what he most cherishes from having been cartoon editor at that magazine for two decades is the opportunity to mentor new talent — a type of creative engagement that helps fuel his new projects at Esquire, including dedicated full-page features for expanded cartooning.

“All in all,” Mankoff says, “this second bite at the apple has been delicious.”