To say that Jules Feiffer’s career is unique is an understatement; who else has won a Pulitzer Prize, an Academy Award, lifetime achievement awards from both the Writers Guild of America and the National Cartoonists Society, and an Outer Circle Critics Award, after all? What other cartoonist can boast collaborations with both the creator of The Spirit and the director of MASH, not to mention a regular gig with the New York Times? Feiffer has been, throughout a career that’s lasted three quarters of a century, a trailblazer and, thankfully, a rewardingly restless presence.

It would also be an understatement to say that Feiffer started early; he was just 17 when he began working for Will Eisner. He famously once described his initial position as being the cartoonist’s “groupie,” hired more for his enthusiasm and knowledge of Eisner’s career than any innate talent, although it wasn’t too long before he became an integral part of the weekly Spirit strip, moving from general art clean-up to guiding the direction of the series while Eisner increasingly took a back seat creatively.

The shift came when Eisner and Fieffer both realized that the latter had more interest in — and more of a gift for — writing than illustrating; Eisner ceded the writing of The Spirit to his protege as Wally Wood took over the art chores, leading to the famous “Outer Space Spirit” cycle of stories, in which crimefighter Denny Colt left Midway City and the serial attempted to jump onboard the science fiction craze of the early 1950s. It wasn’t enough to save the feature from cancellation, but Feiffer was on the verge of bigger, brighter things.

Before he’d get there, there were a couple of false starts to get through. He made two separate attempts to get into animation, first with Mr. Magoo producers United Productions of America, and later — following a brief stint as a member of the Army Signal Corps, where he’d continued to work as a cartoonist, creating Munro, a strip about a four-year-old accidentally drafted, perhaps illustrating his own experiences through metaphor — with the TerryToons animation studio, where he created Easy Winners, a pilot intended to out-Peanuts The Peanuts. It sadly didn’t go anywhere.

In the wake of these misfires, Feiffer ended up at the newly launched Village Voice newspaper a year after its debut, launching a weekly run that would continue for more than four decades, and creating a relationship with the paper that continues to this day. His weekly strip — initially titled Sick Sick Sick, before becoming Feiffer’s Fables, and eventually just Feiffer — looked like the work of an entirely different creator than his earlier work with Eisner and Wood; drawing as well as writing, the strip was a free form ongoing examination of then-modern anxieties and obsessions in relationships, politics, and life in general, presented in a style that’s almost childlike and gloriously sloppy. A subtitle for the strip’s first collected edition, released in 1958, said it all, knowingly describing his work as “a guide to non-confident living.”

The strip was a near-immediate success, gaining the attention of everyone from other editors — Feiffer also started to contribute to the British Observer newspaper, as well as Playboy magazine — to film director Stanley Kubrick, who invited Feiffer to collaborate on a movie adaptation in 1958; the project failed to come together, creating one of the great What Ifs of 20th century pop culture.

Nonetheless, Feiffer’s horizons were expanding. He illustrated Norton Juster’s timeless children’s book The Phantom Tollbooth in 1961, cultivating an audience he’s further explore through a number of children’s books created on his own, including Henry, the Dog with No Tail and The Daddy Mountain, and moved into adult prose with 1963’s Harry the Rat with Women. While he hadn’t managed to make the move into movies with Kubrick, he did become a playwright with 1967’s Little Murders — salvaged from an abandoned novel, and debuting on Broadway with a cast including Elliott Gould — beginning a chain of events that would, indeed, take him to the silver screen in a circuitous route.

Feiffer’s first movie was 1971’s Carnal Knowledge, directed by Mike Nichols. It didn’t start as a movie, however; like Little Murders, its origins lie in another medium, with the project originally written for the stage before Nichols declared that it would work better as a movie. The success of the movie — a critical success and nominated for a number of awards, including a WGA “Best Written Comedy” award — led to further screen work, most notably collaborating with Robert Altman on the 1980 adaptation of Popeye… not only a callback to Feiffer’s own past on newspaper comics, but also his temporary role as a comic historian with the 1965 non-fiction book The Great Comic Book Heroes.

Throughout all of this, Feiffer continued as a cartoonist, with regular cartoons in the Voice and elsewhere, allowing him to explore the world via his finely tuned sense of humor and a line that was as unsteady and filled with motion and emotion as any cartoonist has managed. To look at a Feiffer cartoon is to feel it, it seems, with such meaning and information packed into such deceptively simple drawings as to seem almost impossible and inhuman — an irony, considering just how heartbreakingly human and filled with empathy and kindness Feiffer’s work is, even at its most generic.

If all of the above wasn’t enough to underscore Feiffer’s polymath bona fides, let’s note that he also created one of the first graphic novels as audiences understand the format with 1979’s Tantrum; more than thirty years later, he’d release Kill My Mother, a graphic novel that he humbly described as his “first and only attempt to be a professional cartoonist.” If the rest of his staggering career is the result of him not trying hard, it’s an indicator of his immense talents… and a sign that the rest of us need to have more fun.

CHLOE MAVEAL is the Culture Editor for NeoText and a freelance journalism bot based in the Pacific Northwest who specializes in British comics, pop culture history, fandom culture, and queer stories in media. Her work has been featured all over the internet with bylines in Polygon, Publishers Weekly, Comics Beat, Shelfdust, and many others. You can find Chloe on Twitter at @PunkRokMomJeans.