Orange Alert

‘How About Never?’ Capturing the Essence of Life in Cartoons

A&S alumnus Bob Mankoff’s liberal arts experience at Syracuse was a launchpad for a successful career in the cartoon industry.

May 2, 2024, by Dan Bernardi

Bob Mankoff
Before becoming a prominent cartoonist, Bob Mankoff, an alumnus of the College of Arts and Sciences' Department of Psychology, was crafting his comedic talents on the campus of Syracuse University.

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, 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. But before his successful career in the cartoon industry, he was molding his comedic identity on the campus of Syracuse University, where he majored in psychology and graduated in 1966.

Mankoff grew up in Queens and from an early age was recognized for his artistic talents. 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. With his high school peers living in different parts of New York City, he says his closest friendships were those with his neighbors in Queens. 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.

Shipping up to Syracuse

When it came time to pursue his post-secondary education, Mankoff was torn between Queens College near his home or Syracuse University. 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 Syracuse, 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 Syracuse 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.”

Bob Mankofff SU 1965
A 1965 portrait of Bob Mankoff which appeared in the Daily Orange.

It wasn’t just his comedic ability either. In the early and mid-1960s, a time when most men on campus were clean shaven, Mankoff broke the mold by sporting a goatee. This drew the attention of the Daily Orange student newspaper, who published a feature article highlighting people on campus with goatees, which included an image of Mankoff. His basketball talents also gained the notice of some notable athletes on campus.

“I was there at the same time with Floyd Little and Dave Bing,” says Mankoff. “Although I never tried out for the varsity team, I was a good basketball player and remember playing pickup games with Dave Bing. I think I even recall scoring against him. I was a big basketball fan so following the team was a big part of my experience at Syracuse.”

As can be expected with anyone trying to recall specific memories from 60 years ago, Mankoff notes that the particulars from his days on the hill are a bit hazy, but what he does often reflect on are the relationships, the emotions and the impressionistic feel of that time.

“All of these experiences can't be underrated,” he says. “Part of what college does is socialize you and start to give you a freedom to explore who you're going to be.” And 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 Syracuse set me on a lifelong path to respect learning.”

Bob Mankoff Life and Career Snapshot

1944 - Born in Queens
1958 – 1962 – Attends the Fiorello H. LaGuardia High School of Music and Art in Manhattan
1962 – 1966 - Attends Syracuse University, graduating with a degree in psychology
1974 – Attends the Ph.D program in experimental psychology at the City University of New York and eventually leaves to pursue a career in cartooning
1977 – After submitting 2,000 cartoons to The New Yorker, Mankoff has his first sketch published and signs a contract with the magazine
1992 – Launches Cartoon Bank, a cartoon licensing platform
1993 – Publishes the cartoon, “How About Never--Is Never Good for You?” which becomes The New Yorker’s best-selling cartoon
1997 – Named cartoon editor of The New Yorker
2017 – Leaves The New Yorker and becomes humor editor for Esquire for two years
2018 – Launches Cartoon Collections, parent company to, which offers the world’s largest online database of cartoons for licensing

The Psychology of Humor

A liberal arts education in the College of Arts and Sciences exposes students to a wide range of classes and learning experiences. Through a curriculum that immerses them in coursework spanning the sciences and humanities, they gain knowledge and perspectives that will serve them throughout their career, even if their chosen field eventually differs from their major. For Mankoff, he credits his liberal arts education for helping him to remain curious and continue to learn throughout his life.

“I think it is hubristic to only focus on one area of study and not engage with all this past knowledge that humanity has acquired,” he says. “A liberal arts education illustrates the idea that now is as it was and as it will be. Reading Blaise Pascal, Montesquieu or any of these important thinkers, you'll say, the knowledge is all there. We've been here before and that’s what a liberal arts education teaches you, that the human experience remains the same.”

For Mankoff, his academic interests in psychology and philosophy have informed his comedic pursuits. At Syracuse, he enjoyed exploring philosophical questions like determinism and free will, and investigating the psychology behind what motivates people’s actions and what makes things funny. Those curiosities coupled with his deep understanding of comedy and the creative process even inspired him to teach classes later in his career on the psychology of humor at Swarthmore College and Fordham University.

“The psychology of humor is actually a fairly well researched topic,” says Mankoff. “In my classes we discuss humor theory (why something is funny), superiority theory (comedy based on the misfortunes or others), incongruity theory (juxtaposition of contradictory elements) and benign violation theory (humor that goes against one’s beliefs but in a safe or acceptable manner). And while these are all fascinating to study, none of them will tell you how to create a joke.”

Finding Career Success

When people ask Mankoff how he found success as a cartoonist, his response is that he really had no choice.

“I couldn't do anything else,” he admits. “I worked for the welfare department; I was terrible. Every place I worked wanted to fire me because I wasn't a good employee. With my Jewish background, being funny is part of that culture, and I knew comedy was my true calling.”

In a different world, Mankoff notes that he might have been a stand-up comedian, but limited opportunities and the bruising nature of the business had him choose a path as a cartoonist.

“Cartooning was safer because there was a buffer and in 1972 there weren’t a lot of places where you could workshop stuff nor were there books about how to do stand-up,” he says. “But with cartooning, I could look in the library at all the cartoons in The New Yorker and I could look at magazines, so I could immerse myself in all that.

Cartooning was a passion for Mankoff that took shape on the campus of Syracuse University. 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 Syracuse, which he tried to sell to magazines in the late 1960s after he graduated.

Cartoons created by Bob Mankoff as a student at Syracuse University.

Cartoon drawing of a prisoner with sun streaming through the window.

Bob Mankoff Cartoon of Husband Talking to Wife.

“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.”

Following this setback, Mankoff decided to put his cartoon career on hold and pursue a doctoral degree in experimental psychology at the City University of New York. But it did not take long before he figured out that this career path was not for him. He left graduate school and began cartooning again. While he started to have some luck selling to various magazines, garnering the attention of high-level publications remained elusive.

After submitting around 2,000 cartoons to The New Yorker, he finally got his big break and had one of his comics published. Soon thereafter, 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 of all time, “How About Never--Is Never Good for You?”

Cartoon drawing of a man on the phone with a cityscape in the background.

“How About Never -- Is Never Good for You?” by Mankoff became The New Yorker’s best-selling cartoon of all time. 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.”

In 1997 he would transition away from cartooning when he was named cartoon editor of The New Yorker.

“That was my first time serving in that type of role in a very big organization,” says Mankoff. “I went from being a freelance cartoonist where my day was my own as a creator, to having a set schedule. There were great amounts of satisfaction in bringing new cartoonists in and mentoring them.”

Supporting other cartoonists has remained an important mission for Mankoff. His own experiences as a struggling cartoonist motivated his pursuits to elevate the work of others. In 2018 he created Cartoon Collections, which through its website, features over 500,000 cartoons from artists whose work has been featured in The New Yorker, Esquire, The Wall Street Journal and other publications. Anyone can purchase and digitally download these cartoons for personal or business use. This in turn creates financial support for cartoonists, preserves cartooning as an art form, and develops new opportunities for comics.

“This is really for the benefit of the cartoonists,” says Mankoff. “Fifty percent of all the revenue for the sales of the cartoons goes directly to them. It's hard to be a cartoonist, so if I can help others sell their work, I’m thrilled to be a part of that.”

Tina Brown, former editor of The New Yorker, once said, "Bob is not only a brilliant cartoonist himself, he's also an impassioned promoter, defender and curator of the art of cartooning."

“I'm approaching 80 and I'm grateful to still be doing all this; and if I wasn't doing all of this, I might not be approaching 80,” jokes Mankoff. “People say it keeps you young. Spoiler alert, it does not keep you young. You still get old! But it keeps you engaged and that's important.”

This entrepreneurial spirit and commitment to helping fellow artists embodies the strengths of the liberal arts experience, where students gain the hard knowledge and soft skills to be engaged global citizens and vital contributors to human thriving.

Media Contact

Dan Bernardi