That’s Not Funny: Jack Pittman’s Career As a Cartoonist

Jack Pittman has made a living as a cartoonist through a mix of talent and persistence.
by Joel Haas | photography by Whitney Atkins

You’ve probably seen his work—but it’s likely you don’t know his name. One of the most successful cartoonists in America and abroad has been working in Raleigh for almost 40 years, but he doesn’t have a comic strip or a licensed superhero. Instead, Jack Pittman has built his international reputation as an outstanding commercial cartoonist.

People of (ahem) a certain age will remember “Draw Me” ads on matchbook covers and in the backs of comic books and magazines. The Art Instruction School, a correspondence school, promised a grand prize of a five-year-long monthly cartoon course with all the materials for their annual contest.

Pittman won the grand prize. The mail-order company never expected he would last the whole course—but they didn’t know Jack.

Pittman received his Art Graduation Certificate by mail in 1974, the same week he graduated summa cum laude from North Carolina State University with a degree in Environmental Architecture.

Three months later, Pittman quit his first and only architecture job. “The most boring job in the world,” he says. He wanted to make his living drawing and selling cartoons.

But Pittman encountered a problem: nobody bought his cartoons. He kept the post office busy for months, sending out cartoons every week on expensive, illustrator’s cardboard. Just as regularly, the self-addressed envelopes came back rejected. His only freelance jobs were drawings for company flyers and paintings for billboards.

Finally, that November, Pittman took his portfolio to The News & Observer. The paper didn’t really need anybody to draw full-time. But they did need somebody to airbrush bridal photos and risqué movie ads. “I was traumatized,” Pittman recalls. “I airbrushed away so many belly buttons that I almost never draw them on my characters.”

Married by this point and with a growing family, Pittman settled into a routine: he’d work at the paper, come home to his wife and three small children, and draw more cartoons late into the night to mail out. Businesses needing clever advertising cartoons began to buy his work. After eight years at The News & Observer,  Pittman had enough outside business to try freelancing a second time.

Twelve years later, in 1995, he won his first of three Reuben Awards (an annual recognition from the National Cartoonist Society) in the advertising division. He won again in 1998, and the third time in 2004, in the magazine illustration division.

There ceremonies were a chance to connect with other cartoonists. “I was awestruck after my second Reuben when Peanuts creator Charles Schulz asked me to brunch, says Jack Pittman. MAD magazine artist Jack Davis presented him with his second Reuben, and MAD cartoonist Sergio Aragonés presented the third. Pittman says the highest compliment he ever got, though, was when MAD editor Nick Meglin told him, “If only you’d been born 10 years earlier, you could have been one of the original ‘Usual Gang of Idiots’ rather than a later addition.” After winning the Reubens, art directors knew Pittman’s name and sought him out.

Today, Pittman says, “I’ve been in the business so long that the old art directors who knew me have retired and the new ones are rediscovering me.” And new projects have opened up, too: a few years ago, he was discovered by owners of amusement and water parks; now he has a constant stream of requests to draw comical cartoon maps.

One local account Pittman has kept up with is horticulturalist Tony Avent of Plant Delights in southern Wake County. The two of them get together to lampoon politics and culture for the front of Avent’s plant catalog.


Pittman passed on the art talent gene to his children: one is an expert in 3D computer modeling, another does general illustration work and has an online cartoon strip (Jaywalkin’ On the Wild Side), and the third has a master’s degree in library science and paints as a hobby. “When they were small, I’d draw the cartoon, ink in the black lines and then photocopy it so they could each color it in,” says Pittman.

“Talent though,” he warns,” is a wasted gift without discipline.” He advises budding cartoonists to “practice, practice, practice learning the fundamentals, and be persistent and consistent when others around you tell you you’re being impractical or unrealistic.”

When not drawing, Pittman might be found teaching Adult Bible Study at Forest Hills Baptist Church, or playing drums in a local band. Recently, he became a doting grandfather to his daughter’s baby son. He and his high school sweetheart, Carol, now live in their hometown of Sanford, though Pittman maintains a part-time studio in Raleigh.

By now, nearly all the magazines that rejected his submissions 40 years ago have published Pittman’s work. “The rewards of persistence paid off!”