Bob Mankoff picks his 11 favorite New Yorker cartoons ever

Bob Mankoff picks his 11 favorite New Yorker cartoons ever

Posted by: Helen Walters
June 26, 2013 at 12:14 pm EDT
Bob Mankoff: Anatomy of a New Yorker cartoonBob Mankoff lives and breathes cartoons. He’s drawn many himself — he’s had a contract with The New Yorker for more than 30 years and, in 1997, he became the magazine’s cartoon editor. It’s now his job to sift through the 1,000 or so “idea drawings” (as they’re called within The New Yorker‘s walls) that are submitted each week — and decide upon the 17 or so that will make it into print. As Mankoff explains in great detail in today’s TED Talk, he has a keen idea of what works within the context of the cerebral pages of his magazine. And he’s built up a stable of his own favorite drawings over the years. We asked Mankoff to do the unthinkable and reveal in public some of the cartoons he finds perennially delightful. With typical good humor, he not only did so, but added his own wry commentary on why exactly he deems these cartoons perfectly New Yorker-worthy. Here, in chronological order, his top eleven. Enjoy.


“This is a simply perfect cartoon; it’s perfectly constructed,” says Mankoff. “We have no empathy or sympathy for the pain-in-the-ass old biddy. Then there’s this guy, this shoe salesman, bringing out hundreds of shoes. We think he’s reaching for another black shoe and it turns out he’s reaching for a gun. But this is important: we know he’s not going to kill her. If he shot her, it’d be horrible. This is fantasy, not reality.”Chon Day, December 14, 1946.


“This is so poignant, and I picked it to show off the range of New Yorker cartoons,” Mankoff explains. “It doesn’t work like the others, it really has mixed resonance. Mick is a saxophonist, and the cartoon shows off a barren landscape which is broadly symbolic. It’s not funny, but to me it’s about life without art. This is something that could only have appeared in The New Yorker.”Mick Stevens, December 17, 1979.


“You can’t go wrong with stupidity,” says Mankoff wryly. “When in doubt, make fun of an idiot.” He relents: “But this is done in a lovely way; it’s a lovely drawing. The guy who’s doing this stuff is dumb, but the cartoon is clever.”Jack Ziegler, July 11, 1988.your-age-on-the-dot1

“This is a great cartoon, really, because it’s humor that is meaningful and absolutely true,” says Mankoff. “If we look at the obituaries and see our own age there, it’s chilling.”Roz Chast, October 25, 1993


“Cartoons are either in the realm of reality or fantasy. Everything about this can’t possibly happen; it defies logic and reality and yet it leads to hilarity,” says Mankoff. “‘Fusilli’ sounds like an Italian piece of pasta, but they’re both crazy, because they’re pieces of pasta. Is that ‘Rigatoni’ calling? I don’t know, but it’s one of my all-time favorite cartoons.” Charles Barsotti, November 21, 1994.


“This is about the unbridgeable gulf between what each of us wants and how to interpret another’s feelings,” says Mankoff. “It’s a wonderfully complicated sentence, and we understand it transfers to the very complicated psychological dimensions that separate the two characters from each other.” Bruce Eric Kaplan, October 26, 1998.never-think-outside-the-box1

“This takes an empty-headed cliché and adds a little bit of scatological reference. The two associations make this a great cartoon,” says Mankoff, who adds musingly, “We definitely don’t want cats to think outside the box.” Leo Cullum, November 30,

“If you read The New Yorker, you must know a little about something,” says Mankoff, who submitted his first cartoons to the magazine in 1974. “So you know that’s Einstein, you know about the theory of relativity, you know about sexual relations between men and women. And when you know all that, you know it’s funny.”Eric Lewis, November 13, 2000.


“This is a wonderful example of bringing together two different levels of association, with a tiny bit of disparagement against the French, which is always enjoyable,” says Mankoff with a wink. “Normally it’d be a Swiss army knife but here it’s French so it’s all corkscrews. It’s saying they like wine, which isn’t too bad. It’s not saying they’re inveterate alcoholics. For the viewer, there’s the little cognitive thrill of putting things together.”Michael Crawford, September 10, 2001.che-bart-simpson1

“This is how humor works, by bringing together two different things that usually don’t go together,” Mankoff says. “Usually, revolutionary Che Guevara is the T-shirt, but it turns out he admires another icon, Bart Simpson, a rebel in his own way. There’s a tiny bit of disparagement here; Che is a little downcast. But Bart wearing Che wouldn’t be funny.” Matt Diffee, February 2, 2004.


“This is just a wonderfully constructed cartoon,” Mankoff explains. “You don’t know what the guy will say and it’s all a surprise.” Subversion is at work here. “Of course it’s good that gays and lesbians are getting married, but the reference is to marriage itself, which is a fertile source for humor,” Mankoff continues. “Not when it’s a good marriage; there are no cartoons about good marriages, but there sure are a lot of cartoons about bad marriages.”Michael Shaw, March 1, 2004.

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Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (, the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

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