Becoming a great comedian or cartoonist doesn’t happen overnight. As with many professions, it takes tremendous commitment and practice, a bit of failure and some luck along the way. For Bob Mankoff ’66, these were all part of his journey to becoming a prominent cartoonist and cartoon editor for major publications such as The New Yorker and Esquire.
Bob Mankoff
Mankoff grew up in Queens, New York, and was recognized for his artistic talents from an early age. He attended the prestigious Fiorello H. LaGuardia High School of Music and Art, a specialized school in Manhattan for students who excelled in fine arts. Each day, he would take a bus and three subway trains to get to school.
Despite living in a New York City borough of around 2 million people, he notes that his upbringing had a very small-town feel. This factored into his decision to explore a new and unfamiliar opportunity after high school: studying psychology at ϲ, where he both molded his comedic identity and used that liberal arts experience as a launchpad for his successful career in the cartoon industry.
When it came time to pursue his post-secondary education, Mankoff was torn between Queens College near his home or ϲ. He ultimately decided to head upstate to Central New York for a change of pace and a chance to explore his identity.
“College is almost like going to the army in a way,” says Mankoff. “You’re just thrown in with a whole new set of people that you don’t know and that’s a shock and an opportunity. The opportunity is you get to invent yourself if you have something to invent. I had something to invent. I knew I was funny and creative.”
Once he got to ϲ, his strong personal presence and ability to make others laugh soon came to the fore, and it didn’t take long before his humorous antics gained him notoriety across campus.
“I did a lot of outrageous things at ϲ that many people still remember,” says Mankoff. “There was a rule in the cafeteria that you had to wear socks, so I painted my socks on. What was driven home to me was the power of humor as a subversive force that lets you have an identity within an institution.”
It didn’t take Mankoff long to figure out that his future might involve comedy.
“In English 101, one of the first classes I took, we had to write an essay and I took a humorous approach,” Mankoff says. “The arc was I’m an only child, I’m coming from Queens and I’m going to be all by myself, so who’s going to take care of me? I found out that my roommate is such a neat freak that he’s going to be the one ending up serving that role. While handing back the papers, the English teacher said, ‘Here is a really interesting and good one,’ and he had me read mine to the class. Having the teacher respond to my humorous paper in a positive way was affirming. Being exposed to this experience at a university like ϲ set me on a lifelong path to respect learning.”
Cartooning was a passion for Mankoff that took shape on ϲ’s campus. In his book, “How About Never—Is Never Good for You?,” Mankoff spotlights some of the gag-style cartoons he developed while a student at ϲ, which he tried to sell to magazines in the late 1960s after he graduated.
“Nobody bought any,” he says. “I did 27 cartoons and thought well, how many more cartoons could anybody do? In retrospect, I can see that the editors were encouraging, but I was young. I didn’t think they were encouraging, I thought they were idiots for not seeing my genius.”
Over the next 20 years, Bob Mankoff would publish nearly 1,000 cartoons in that magazine, including his most popular and best-selling comic of all time, “How About Never—Is Never Good for You?”
Eventually, after submitting around 2,000 cartoons to The New Yorker, he finally got his big break and had one of his comics published. Soon after, he signed a contract with The New Yorker, solidifying his budding cartoon career. Over the next 20 years, he would publish nearly 1,000 cartoons in that magazine, including his most popular and best-selling comic, “How About Never—Is Never Good for You?”
“How About Never—Is Never Good for You?” by Mankoff became The New Yorker’s all-time best-selling cartoon. He attributes its popularity to aligning with people’s feelings about meetings at that time, and even more so now, saying “People have to very carefully manage who they talk to and how much they talk to them. I think it hit that moment and it’s a good gag.”
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