Al Jaffee, the pioneering Mad magazine cartoonist and inventor of the “fold-in” who worked for the publication for seven decades and retired when he was 99 years old, has died at the age of 102.

Jaffee died on Monday in a Manhattan hospital of multi-system organ failure, his granddaughter told the New York Times.

The Guinness record-holder for longest career in cartooning, Jaffee was known for inventing several of Mad’s most famous regulars, including Snappy Answers to Stupid Questions and the magazine’s iconic “fold-in”, the illustration that ran on the back inside cover of every issue that, when folded, revealed a second hidden image. The fold-in was originally designed to mock the centrefolds in magazines such as Playboy.

Speaking to the Guardian in 2016 at the age of 95, Jaffee said he believed satire was becoming harder in the face of politicians who felt no shame about lying. “I think they’re defeating Mad, because they’re going beyond anything we can think of doing to show the clownish nature of their claims,” he said. “It used to be that politicians claimed that they would make jobs for everybody in the country within two years or something like that; now they claim that they’re going to make jobs for everybody on Mars.”

Born Abraham Jaffee in 1921 in Atlanta, Jaffee began working in comics soon after graduating high school. At just 20 he sold a parody of Superman, titled Inferior Man, to comic heavyweight Will Eisner, and a year later began working for soon-to-be Marvel titan Stan Lee. He began going by the name Al during the second world war, as a way to protect himself from antisemitism. During the war, he worked at the Pentagon, making pamphlets and posters for the war effort.

Jaffee joined Mad in 1955, three years after it launched. Aside from the famous regulars he invented, he was also well known for the anti-war cartoons Hawks & Doves, which he drew during the Vietnam war. His fans included Charles M Schulz of Peanuts fame, Far Side creator Gary Larson, and satirical comedians Jon Stewart and Stephen Colbert, who marked Jaffee’s 85th birthday by featuring a fold-in cake on The Colbert Report. When Stewart and The Daily Show writers wrote the bestselling book America (the Book), they asked Jaffee to create a fold-in for it.

“When I was done, I called up the producer who’d contacted me, and I said, ‘I’ve finished the fold-in, where shall I send it?’ And he said – and this was a great compliment – ‘Oh, please Mr Jaffee, could you deliver it in person? The whole crew wants to meet you,’” Jaffee told the Boston Phoenix.

When he retired in 2020, at 99, he was the magazine’s longest-tenured contributor. He was a freelancer for his whole life, and never became a staff member. Towards the end, he mainly worked on fold-ins, each of which took him roughly two weeks of work.

“I had two jobs all my life,” Jaffee told the New York Times on his retirement. “One of them was to make a living. The second one was to entertain. I hope to some extent that I succeeded.”

Jaffee is survived by his children, Richard and Debora; two stepdaughters, Tracey and Jody; as well as five grandchildren, a step-granddaughter and three great-grandchildren.