The British Royal Mail has issued a set of eight postage stamps celebrating this November’s 100th anniversary of the beloved children’s-comic-strip character Rupert Bear. The stamps feature illustrations and rhyming couplets from the Rupert Annuals drawn by the reclusive artist-writer Alfred Bestall (1892–1986). The images are mostly heartwarming, but some convey a sinister bent which crept into Bestall’s tales.

Initially conceived by children’s artist Mary Tourtel, whose husband was a night editor for the Daily Express, Rupert was launched in a serialized strip in the newspaper on November 8, 1920, to compete with the Daily Mail’s cartoon mouse, Teddy Tail. Bestall, a trained artist who drew sophisticated panels for Punch and Tatler, took over in 1935, when Tourtel’s eyesight began to fail.

One of the eight newly released Royal Mail postage stamps commemorating the 100th anniversary of Rupert Bear.

“As far as I’m concerned, it’s then the magic starts,” said Monty Python’s Terry Jones, who directed a labor-of-love documentary, The Rupert Bear Story: A Tribute to Alfred Bestall, in 1982.

Whereas Tourtel’s passive Rupert relied on miracles for deliverance from ogres, ravens, and the like, Bestall’s plucky Rupert taught children to accept that bizarre things happen and to be courageous and resourceful. To millions of kids for whom Rupert was a boon and comfort during the London Blitz and who still buy the annuals as octogenarians, Rupert’s ability to thwart villains and return safely home made him a symbol of British fortitude. The annuals sold 1,750,000 copies at their peak, in the 1940s. Bestall, a shy, lifelong bachelor who’d been a transport driver in World War I and who stuttered until he was 45, told Jones that Rupert allowed him to escape. Nevertheless, until Tourtel died, in 1948, Bestall refused to sign his drawings.

Rupert’s ability to thwart villains and return safely home made him a symbol of British fortitude.

While Bestall’s Tatler spreads were often discreetly erotic—he excelled at pretty flappers and languorous socialites—Rupert would become his life’s work. Though poorly paid, Bestall wrote and drew the daily strips until 1965; the annuals continued to use his covers until 1973 and his stories into the late 70s. (The strip, drawn by various artists, has continued to run in the Daily Express.)

Alfred Bestall (right) in 1947, showing a Rupert Bear book to George C. Marshall, the U.S. Army general and Nobel Peace Prize–winning architect of the Marshall Plan.

Wearing a red sweater, bright-yellow checked trousers, and matching scarf, Rupert dwells in the timeless rural village of Nutwood with tweedy Mr. Bear and aproned Mrs. Bear, and experiences Baron Munchausen–worthy escapades that send him to tropical locales and unearthly realms (also to West Country sands, coves, and caves). He whooshes through tunnels and flies in mechanical contraptions and balloons; sometimes he just flies. Even Rupert’s scrapes in his local woods involve baffling spells or physical conundrums. His world is as enchanted as J. R. R. Tolkien’s Middle-earth. Visiting the toucan king of the birds, Rupert rides on an eagle’s back (as portrayed on one of the centennial stamps).

Anticipated by Winsor McCay’s fantastical “Little Nemo” strip, which debuted in the New York Herald in 1905, Bestall’s stories blend realism and surrealism and revel in witty wordplay. Expecting a “nice boat” for Christmas, Rupert receives “an ice boat,” so naturally he has to visit Santa Claus. In a more visceral saga, Rupert and his friend Algy Pug are thrown from a ship and travel to an island, where they team with an army of snakes to rout “cruel” Black cannibals who’ve captured the ship’s white crew. This tale is sparked by Rupert’s being given a cricket set in his living room.

Though Bestall had progressive leanings, his unfortunate use of ethnic stereotypes and racially insensitive words led to 11 of the 1936–70 annuals being withheld when the rest began reappearing in facsimile editions in 1985. Female characters such as Ottoline Otter, Rupert’s Shakespeare-loving gal pal, and Rika, a human Laplander, were added by one of Bestall’s successors, John Harrold.

Bestall’s resourceful Rupert Bear was a comfort to British children during the London Blitz.

Jones was a champion of vintage British juvenile literature—he directed a live-action version of Kenneth Grahame’s The Wind in the Willows in 1996—and was especially passionate about Bestall’s anthropomorphic boy adventurer. When Jones died, in January, his funniest Python personae—including the nude organist, the Spam waitress, the barfing diner Mr. Creosote, and all those kvetching housewives—elicited fond collective memories. It was not for his anarchic meta-comedy that Jones wished to be remembered, however; it was as a prolific children’s author and for “some of my academic stuff.” (A medievalist, he wrote two books on Chaucer.) The film culminates with Jones interviewing Bestall, then 90, at his Welsh cottage (near Jones’s birthplace). Available on YouTube, the documentary is ripe for re-discovery and includes an interview with Paul McCartney, whose sublime animated short film “Rupert and the Frog Song” (1984) was inspired by one of Bestall’s panoramic annual endpapers.

Introduced to Americans on Nickelodeon, Rupert has strayed from his storied past in five TV series. While he survives in the Daily Express and the annuals, without Bestall’s particular genius and empathy he lacks the old power to enchant. It’s hard to argue with Jones’s belief that the 1936–50 Rupert annuals are among “the greatest children’s books of all time”—or that Bestall’s Rupert evokes a wonderland of the mind as indelible as Alice’s.

Graham Fuller is a New York–based film critic