The long and tangled history of Alfred E. Neuman.

In a 1975 interview with the New York Times, MAD Magazine founder Harvey Kurtzman recalled an illustration of a grinning boy he’d spotted on a postcard in the early fifties: a “bumpkin portrait,” “part leering wiseacre, part happy-go-lucky kid.” It was captioned “What, Me Worry?”

That bumpkin became Alfred E. Neuman, MAD’s mascot, who turns sixty this year—kind of. The impish, immutable redhead made his official debut in December 1956, when he appeared on the cover of MAD no. 30 as a write-in candidate for president. He’s appeared on almost every MAD cover since: possessing, spoofing, and spooking cultural icons with nothing more than a drowsy rictus. Though MAD gave him a purpose, a permanent home, his origin story remains elusive. It involves, among other things, a plum-pudding advertisement, a dubious lawsuit, and a traveling nineteenth-century farce. Neuman is forever synonymous with the magazine and its infinite irreverence, but the riddle of his real age may be the trickster’s trump card.

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In the corners of MAD’s early issues, Kurtzman deployed the “What, Me Worry?” face as a miniature visual motif that would pop up in the margins of the publication’s densely-packed black-and-white pages. When Al Feldstein inherited editorial control from Kurtzman in 1956, he made the boy the full-color magazine’s new figurehead. Mascots by then had become a point of prestige: Playboy had its bunny, The New Yorker had Eustace Tilley, Esquire had the wide-eyed Mr. Esky. “I decided that I wanted to have this visual logo as the image of MAD, the same way that corporations had the Jolly Green Giant and the dog barking at the gramophone for RCA,” Feldstein told the A.V. Club in 2007.

Feldstein commissioned Neuman’s first cover portrait from Norman Mingo. A sixty-year-old veteran of commercial illustration, Mingo’s specialty was Vargas-style pinups and Norman Rockwell–esque portrayals of middle-class American culture. He was near retirement when he responded to a New York Times ad that read ILLUSTRATOR WANTED . A born-again Christian, Mingo recoiled when he first visited the magazine’s headquarters at 485 “MADison Avenue,” but his luxuriant style was a perfect fit for the burgeoning publication, and he needed the work. Beginning with the Neuman assignment, he ended up painting most of MAD’s covers for the next twenty years.

For the half-length color painting of their red-haired mascot, Feldstein told Mingo that he didn’t want the boy to “look like an idiot—I want him to be lovable and have an intelligence behind his eyes. But I want him to have this devil-may-care attitude, someone who can maintain a sense of humor while the world is collapsing around him.” MAD insiders referred to the kid by various names—Mel Haney, Melvin Cowsnofsky—but when the magazine won legal rights to the face, he was officially christened Alfred E. Neuman. A pseudonym without a specific host, it was one of many counterfeit names used as running gags in the magazine.

By 1965, when the face had grown in stature to become a familiar punch line in the national culture, the widow of a cartoonist named Harry Spencer Stuff brought a lawsuit against MAD. Neuman, the plaintiff claimed, was a copy of Stuff’s caricature “The Original Optimist,” also known as “Me-worry?”, which he had copyrighted in 1914.

To help fight the infringement claim, MAD searched for and solicited from its readers evidence of the boy’s existence before 1914. The image that Kurtzman first discovered on that postcard turned out to be an itinerant orphan of low-budget advertising, with a trail of appearances dating back to the early twentieth century. He was there on a 1942 matchbook for an auto-parts store in Longhorn, Texas; on the label of Happy Jack, a soda produced in 1939; on the menu for a coffee shop in Ashland, Nebraska; in a 1908 calendar for antikamnia, a cure-all painkiller spiked with heroin; in a 1905 ad for “painless dentistry,” beneath the quip, IT DIDN’T HURT A BIT! ; and in a 1902 playbill for Maloney’s Wedding Day, a small-market musical comedy. Every graphic centered on a portrait of a kid with mussed red hair, saucer ears, and a shit-eating grin, minus a tooth. Stuff may have codified the image, giving the boy the sleepy grin and tilted posture, but earlier iterations suggested that his caricature was itself a modified copy. The court ruled in MAD’s favor: Neuman was a fatherless mutant of the public domain.

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In Completely Mad, her comprehensive 1991 history of the magazine, the writer and researcher Maria Reidelbach traced the earliest Neuman antecedent to 1895, in an advertisement for Atmore’s Mince Meat and Genuine English Plum Pudding. “The kid’s features are fully developed and unmistakable,” Reidelbach wrote, “and the image was very likely taken from an older archetype that has yet to be found.”

Peter Reitan doesn’t believe in untraceable archetypes. A patent attorney based in Irvine, California, Reitan devotes his spare time to researching arcane threads of pop culture. Under the pseudonym Peter Jensen Brown, he collects his work in a series of personal blogs. One is dedicated to “The Dude-craze of 1883.” Another focuses on the evolutions of Bozo the Clown. A former competitive Scrabble player, Reitan relishes etymologies with supposedly unknowable origins: “the whole nine yards,” “the whole shebang,” “23 skidoo.” “I like looking at things that seem mysterious,” he says. “Once you get enough early information, they seem less mysterious.”

In late 2012, Reitan was trawling the online newspaper database Chronicling America for information about the Cuban Giants, the first African-American professional baseball club. (Early sports histories are another of Reitan’s specialties.) Scanning a page from an old Los Angeles Herald, he noticed a familiar face mugging at him from a corner. The scraggly hair, the missing tooth—Neuman. A caption beneath the face read: “What’s the good of anything?—Nothing!” It advertised a play called The New Boy. The paper was dated December 2, 1894.

Reitan had been a MAD reader as a boy, but he was unaware of the ongoing debate over Neuman’s origins. “Finding the image made me wonder,” he says, “and then, when I went looking, I found John Adcock’s Yesterday’s Papers blog, which led to Maria Reidelbach’s book and the Atmore’s Plum Pudding ad … That’s when I figured I might be on to something.”

Reitan’s research turned up a history of The New Boy, a comic farce that had been a smash hit in London and then New York before traveling America in a touring company throughout late 1894 and early 1895. The grinning boy was a rendering of the play’s title character, Archibald Rennick, a thirty-ish man who passes as a boarding-school adolescent so that he and his wife can cash in on an inheritance scheme. The foundational image, Reitan deduced, was probably based on either Bert Coote or James T. Powers, two rubber-faced, red-haired stage actors who starred in the early productions.

As Reitan points out, the advertisement “would likely have been seen in every city where the show played during its three tours over a span of more than five years,” which helps explain the boy’s omnipresence. He was adopted for political caricatures and soon after for more advertising, including the Atmore’s Pies graphic. Each new riff invited another wave of copycats: the character split and multiplied, strengthening its potency as a meme and obscuring any certain origins.

While some MAD theorists insist that Neuman’s history goes back further, to the racist, simian-faced Irish cartoons that Joseph Keppler and Frederick Opper drew in the 1870s, the resemblance becomes more specious in images before 1894. “The fact that so many of the other, similar images cropped up soon after the play opened, and none of them before, suggest that the image originated with The New Boy,” Reitan wrote in his original post:

The pre-1894 cartoon images … may just be random look-a-likes of a funny type, in the same way that Howdy Doody, Opie Taylor, Richie Cunningham, Ron Howard, Rick Astley, and the young Prince Charles looked like Alfred E. Neuman. Let’s face it, redheaded kids with big ears are just funny, a painful lesson that my brother and I learned at a young age, as did our father, uncle, and grandfather before us.

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When Mingo retired in 1976, the task of drawing Neuman passed from Frank Kelly Freas to Richard Williams, Mark Fredrickson, and a host of trusted MAD staffers. In a recent blog post, the illustrator Tom Richmond, who has been with MAD since 2000, outlined the strictures limiting Neuman’s evolution. “I was told early on that any depictions of Alfred should be based solidly on the Mingo original,” said Richmond:

Artists are not allowed to do 3/4’s or profiles of Alfred … We can only draw the front or back of his head directly. I was told not to try and ‘caricature’ Alfred or place my own stamp on his features … Alfred is also never to have a word balloon or have words coming from his mouth (although the editors have broken this rule themselves many times in the magazine’s table of contents, where they have an Alfred “quote” feature). His expression can be changed in certain circumstances, but that is rare and needs editorial approval.

Meanwhile, as old ephemera is unearthed and traded online, Neuman’s family tree continues to thicken. There he is as the clueless supporter of Roosevelt’s 1940 re-election in a postcard produced by Wendell Willkie’s campaign. A World War II snapshot shows Neuman’s face emblazoned on the nose of a C-47 bomber, above “What Me Worry?”

Then there are the more mysterious sightings: a close-up of an old portrait of Sari and Sally—a popular Grand Ole Opry team from the thirties—reveals Alfred’s face in Sari’s broach. A National Geographic photo shows an Austrian folk artist carving a grinning Zell am Moos mask that resembles Alfred. In the basement of a home in Takoma Park, Maryland, someone unearthed a glass negative from 1902 that showed a family posing in a backyard next to a cutout of Alfred’s head. The Stanford chemist Carl Djerassi swore that he had seen the face in Vienna after the Anschluss, with the caption “Tod den Juden” (“Kill the Jews”).

According to Reitan, each appearance can be explained as an exponent of either The New Boy promotions or Harry Stuff’s “What Me Worry” kid. (Reitan surmises that Neuman’s signature motto is a hybrid of The New Boy tagline and the “I Should Worry!” craze of the 1910s.) The more far-fetched sightings can be attributed to a special case of collective apophenia. That people are convinced they saw Neuman in places he never existed only reinforces his ubiquity.

In election years especially, Neuman is the Zen retort to a world of increasingly exhausting absurdity. Though he’s often interpreted as a symbol of idiocy—most prominently in a spate of appearances during George W. Bush’s reign—I never read him as an idiot. I told Reitan that Neuman has the knowing serenity of someone who knows he’s going to get the last laugh. “I have a different interpretation,” said Reitan. “I agree he’s knowing, but I think it’s the look of someone who knows he’ll never get the last laugh.”

As art historians scrutinize the Mona Lisa, MAD fans try in vain to push past their hero’s profound ambiguity in arguments about Alfred’s true age. He looks wizened but he’s not an adult, yet he’s too old to be a “new” boy. Reitan pointed out that the protagonist of The New Boy was an old guy acting like a kid. When I forced him to pin an age on Alfred, he said: “When I was twelve, he looked twelve. Now that I’m fifty-five, he looks fifty-five.”

Sam Sweet is the author and publisher of All Night Menu, five booklets about the hidden histories behind a series of Los Angeles addresses.