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Bob Mankoff
Bob Mankoff
Cartoonist • Humor Editor, Esquire
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Bob Mankoff
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Cartoon and Humor Editor for Esquire and former New Yorker Cartoon Editor, Bob Mankoff believes that “being funny is being awake,” and he has successfully kept us all wide-awake for 40 years. A student of humor and creativity, Mankoff has devoted his life to discovering just what makes us laugh, and seeks every outlet to do so, from developing The New Yorker’s web presence to integrating it with algorithms and A.I.

Joining Esquire in April 2017, Mankoff is reviving the magazine’s legacy of satire and humor in a newly appointed role, editing humor pieces, providing story ideas, and even drafting cartoons himself. While fostering in a new generation of humorists and cartoonists, Mankoff brings his distinctive wit and flair to the most-honored monthly magazine in America.

Twenty years as cartoon editor for The New Yorker, Mankoff pored over literally thousands of submissions; analyzing, critiquing, and selecting each cartoon, he mentored cartoonists, new and old, towards the laughs readers expect. In 2005, he helped start the “New Yorker Cartoon Caption Contest.” With 5,000 reader submissions a week and over 2.5 million entries to date, Mankoff partnered with Microsoft and Google Deep Mind to develop algorithms to help cull the funniest captions.

Mankoff’s career started, unexpectedly, by quitting a Ph.D program in experimental psychology at The City University of New York in 1974. Shortly after, he began submitting cartoons to the New Yorker. Three years and over 2,000 cartoons later, he finally made the magazine and has since published over 950 cartoons. His story and day-to-day at the magazine were the focus of the 2015 HBO documentary Very Semi-Serious

How About Never – Is Never Good For You?: My Life In CartoonsBob’s New York Times bestselling memoir, was published in 2014. The Washington Post said, “Mankoff's deep understanding of humor, both its power and its practice, is the live wire that crackles through his book.” 

Mankoff continues to submit cartoons to The New Yorker while curating its Cartoon Bank, the world’s most successful cartoon licensing platform that he founded in 1992. He is also continuing work on his forthcoming book “The New Yorker Encyclopedia of Cartoons.” In addition to appearances on 60 Minutes and Charlie Rose, Bob was the host of New Yorker web series “The Cartoon Lounge.”

Author of numerous books including The Naked Cartoonist: A New Way to Enhance Your Creativity, Bob has taught classes at Swarthmore, Fordham, and led workshops on the creative process. Working with comedy writer Jamie Brew, he is currently developing Botnik Studios, a company that utilizes A.I. to enhance human creativity and humor.

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  • SXSW 2014 : The Magic of Cartoons
  • hbo royce carlton speaker rci speeches lectures trailer new yorker cartoons
    HBO Documenary "Very Semi-Serious" Trailer (2015)
  • mankoff rci royce carlton speakers cbs 60 minutes new yorker cartoons
    Mankoff takes 60 Minutes Inside The New Yorker (2014)
  • TED speakers royce carlton bob mankoff new yorker cartoons
    TEDTalk: Mankoff "Anatomy of a New Yorker Cartoon" (2013)
  • bob mankoff rci speaker univeristy of michigan
    Mankoff at Univeristy of Michigan, "Past, Present & Future of Humor" (2009)
  • royce carlton rci charlie rose bob mankoff new yorker
    Bob Mankoff (2014)
  • bob mankoff big think interview
    Big Think: Bob Mankoff "Making Sense of Humor" (2009)
  • bbc mankoff new yorker cartoons
    Mankoff tells the BBC "What makes a New Yorker cartoon funny?" (2014)
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Speaking Topics
I ONLY READ IT FOR THE CARTOONS: An Insider’s Cartoon History of The New Yorker

Bob Mankoff is the ultimate New Yorker cartoon insider. He’s been a staff cartoonist for The New Yorker for thirty-five years and its Cartoon Editor since 1997. He sees over a thousand cartoons a week in order to help select the fifteen or so that go into the magazine, which over its long and storied history has published over 80,000 of them.

In this fast-paced and funny multimedia presentation featuring cartoons and videos, Bob ushers you into the hallowed halls of The New Yorker (Shhh! You’ll upset the fact-checkers) to show you the soup-to-nuts process of cartoon creation, giving you not only a detailed look at his own work but that of artists who keep you laughing every week, except, of course, when they don’t, puzzling you with a cartoon that you “don’t get”. What’s up with that anyway? In this presentation, all will be explained including how to increase your odds of winning the famous New Yorker Caption contest.

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THE NAKED CARTOONIST: Exposing your Ideas, Imagination & Wit to Enhance Your Creativity

As cartoon editor of The New Yorker, and one of its most gifted contributors, Bob Mankoff spends his life pursuing that elusive thing called creativity and inspiring it in others. If you’ve ever wondered where great ideas come from, or yearned to channel your creative energies, or just wanted some pointers on how to get those artistic juices flowing — this talk (and his book The Naked Cartoonist) is for you. Along with some help from his well-known cartoonist friends, Bob takes you on an entertaining words-and-pictures journey through the art, craft, and zen of cartooning, along the way providing lots of personal anecdotes about his development as an artist and about life at the world’s most urbane magazine. But you don’t have to be an aspiring cartoonist to appreciate The Naked Cartoonist. Bob’s wisdom, and his practical yet whimsical approach to the creative process, are designed to benefit anyone who has ever stared at a blank piece of paper or canvas and dreamed of transforming it into something truly original (and maybe even commercial). What’s so funny? Bob Mankoff knows best. He also knows how you can find your own personal voice and message, how you can learn from the masters of the past, how you can transform a current event into a comic tour-de-force…even how you can incorporate telling lies and taking naps into your daily routine — and justify it.

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Your Sense of Humor — Don’t Leave Home Without It (General Audiences)

As young kids, most of us were taught that humor is silly and a waste of time. And so, while five-year-olds laugh hundreds of times a day, adults are down to about fifteen. We’ll see how wrong this prejudice is and how humor and other forms of play can enhance our professional effectiveness.

Humor has three main benefits. First, it’s physically and psychologically healthy, especially in the way it blocks stress. Secondly, humor makes us mentally flexible — able to manage change, take risks, and think creatively. And thirdly, humor serves as a social lubricant, making us more effective in dealing with colleagues and clients. We’ll experience all of these using pictures, cartoons, stories, and exercises.


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Laughter and the Professions


  • Humor and Law
  • Humor and Healthcare
  • Humor and Education
  • Humor and Business Executives
  • Humor and Mental Health
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A Passion for Perseverance: If at first you don’t succeed, try 2,000 times

It’s not easy to get your cartoon published in the New Yorker. Just ask their Cartoon Editor, Bob Mankoff. Since 1977, his name has been synonymous with the New Yorker, but he didn’t get there over night—it was actually closer to 1,000 nights. It took three years and 2,000 submissions to see his name in the corner of one of his cartoons. More than talent, getting published took perseverance.

In “A Passion for Perseverance,” Bob Mankoff will show audiences how to stop worrying and love the process of creating. To achieve your goals, you need to be ready for the long haul, but as Bob will explain, the long haul doesn’t have to be a real slog. This fun and interactive program will leave you ready to get to work with a smile on your face.

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ON THE MONEY: Humor in Sales, Marketing, and Customer Service

Did you ever wonder why so many Superbowl commercials use humor? (At the Cannes Film Festival, 95% of the winners in the Advertising category are funny.) Have you noticed how even traditionally staid businesses like banking and insurance are now putting humor into their advertising? We’ll explore six ways humor works with customers. We’ll see how it creates rapport and overcomes sales resistance, opening customers’ minds to new perspectives. And because humor gets customers involved in processing the message, they remember that message better. In customer service, humor provides a moment of unexpected delight. Sometimes this is a bonus — icing on the cake — and sometimes it saves the relationship when things are not going well. We’ll also explore crucial differences between men’s humor and women’s humor and their implications for business. All these topics are explored using pictures, videos, cartoons, stories, and exercises.

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THE CARTOON CAPTION CHALLENGE: Crowdsourcing Lessons in Humor from The New Yorker Cartoon Caption Contests (where your audience also gets to pick the punch lines).

Humor is traditionally at the hand of its author, but what happens when the audience picks the punch line? Each week, on the last page of the magazine, The New Yorker provides a cartoon in need of a caption. Readers submit captions, the magazine chooses three finalists, readers vote for their favorites. It’s humor — crowdsourced — and with more than 2 million submissions provided by 500,000 participants, it provides tremendous insight as to what makes us laugh. In this talk, Bob analyzes the lessons we learn from crowdsourced humor. And then it’s your turn. The sponsor is provided with captionless cartoons for a campus/company wide caption challenge. Mankoff selects the finalists who then compete on stage in a live Cartoon Caption Challenge. It’s winner take some because all contestants get original signed cartoons by Mankoff.

*A shorter audience participation version can be added to any of Bob’s talks.

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FUNNY YOU SHOULD ASK: How & Why Jews Became “The People of the Joke.”

From growing up Jewish in Queens, NY, to going to the Borscht Belt as a kid where he saw performances by Jerry Lewis, Buddy Hackett, and Rodney Dangerfield, among others, Bob shows how his Jewish heritage helped him to become a successful cartoonist and presents a personal and historical cartoon illustrated history of Jewish humor.

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Available for Half-Day and Full-Day Seminars
Books & Other Works
  • The New Yorker Cartoons of the Year 2016
  • How About Never - Is Never Good For You?
  • The Naked Cartoonist: A New Way to Enhance Your Creativity
  • The New Yorker Book of Literary Cartoons
  • The New Yorker Book of Art Cartoons
  • The New Yorker Book of Teacher Cartoons
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“Bob Mankoff is hilarious, generous, and easy and fun to work with. I was excited about his coming to MBA for obvious reasons, but I was even more pleased to get to know him on a personal basis and to see the ways in which he thoughtfully related to our students, faculty, and trustees. He has a brilliant mind and wicked perspective, and students and adults alike enjoyed his sense of humor and view of the world.”
Montgomery Bell Academy
“Inviting Bob Mankoff to give the Plenary Address at the Organization of American Historians Annual Convention in 2015 was my smartest move in my year as president of that group. Inviting him to the University of Colorado, to give the launching talk for our Center of the American West Humor Initiative, was another decision I would rank high for its brilliance. He instantly identifies and aims at the strike zone of his audience's sense of humor, and his energy and charm, along with the lasting power of the insights, make being in his company one of the wisest allocations we can make of our time in the planet.”
University of Colorado
“He was terrific, and I think people enjoyed having a little bit of change of topic from the economy and everything else that's going on. ”
Berkshire Partners
“Bob was so easy to work with; that I feel I can call him Bob. From the very beginning of the process, Bob was accessible and engaged. The evening of the event only served to underscore why he has the job he does. Bob was funny, approachable, interested in the guests/donors and willing to put himself out there the entire evening; not just during his scheduled evening presentation. His presentation was very entertaining and every guest commented how much they enjoyed listening to his stories and appreciated his humor. He was an absolute pleasure to meet and work with and a genuinely, humble person with so much to share with his audience. I would absolutely recommend him to anyone looking for a speaker.”
Hebrew HealthCare
“Everything was fantastic. Bob was great and everyone remarked what a great presentation he gave. People lined up to get their books signed and he stayed around to speak to each and every one of them.”
The New Jewish Home
“Around academe, it is said, 'Those who can’t do, teach.' Nobody 'does' cartooning and humor in general better than Bob Mankoff, an exception to the rule I have had the great pleasure of witnessing at the University of Michigan, where I am a professor and director of journalism programs. Often when new courses appear, particularly when they don’t belong to a single department, enrollment falls over the first few years. Bob’s multidisciplinary enrollments as a guest lecturer grew steadily. He was also a huge hit with the Knight-Wallace Fellows, mid-career journalists from around the US and the world taking a year off for sabbatical study. They are a tough audience. But they know a great source when they meet one and realized in Bob they were encountering not only the top humor editor in the US, but one of leading scholars of the subject, anywhere. ”
University of Michigan
“Bob has a sixth sense for working a room. His rapid-fire mind can integrate the realities of the current audience into a previously prepared talk. At Temple, Bob zeroed in on the most beloved person present (a lawyer who had been practicing for 60 years) and won over the audience by working this man into his talk. At the scholarly conference, Bob paid homage to the academic expertise in the room, but provided desperately needed comic relief.

Bob also has a broad range. Linguists, business academics, students, lawyers: he captivated them all. How? He’s not only really funny, but also emanates natural warmth. Bob has an unusual knack of conveying a “bad boy” persona, while sharing only tasteful and endearing material. It’s not that he walks the line between innocent and naughty. Rather, he somehow conveys both. Pretty much everyone leaves the room happy.”
Temple University's Beasley School
“This is a presenter who is in total command of his material and clearly takes the greatest pleasure in telling the compelling story of what makes cartoons hit home. With no shortage of funny anecdotes and illustations at his fingertips, Bob Mankoff’s impeccable timing ensures that the audience is laughing from start to finish. His reputation is such that the house sold out within days of being published.”
Rubin Museum of Art
Colleges & Universities
Graphic Novels
Health Care
Jewish Issues
Liberal Arts
New York City
Personal Growth
Personal Stories
Popular Culture
Risk Taking
Social Commentary
Student Activities
The Arts
Social Media