A few weeks ago, rummaging around the Strand, I came across a fiftieth-anniversary edition of Shel Silverstein’s “The Giving Tree.” It had the fern-green cover familiar from childhood, the same oversized dimensions, the same appealing sketch on its front—a squiggly drawing of a tall tree, its top spilling off the page, and a little boy, looking up at it. But instead of experiencing a pleasant rush of nostalgia, I was dismayed. A strange thing happens when we encounter a book we used to love and suddenly find it charmless; the feeling is one of puzzled dissociation. Was it really me who once cherished this book?

The beginning of the story is innocuous enough: a boy climbs a tree, swings from her branches, and devours her apples (I’d never noticed that the tree was a “she”). “And the tree was happy,” goes the refrain. But then time passes, and the boy forgets about her. One day, the boy, now a young man, returns, asking for money. Not having any to offer him, the tree is “happy” to give him her apples to sell. She is likewise “happy” to give him her branches, and later her trunk, until there is nothing left of her but an old stump, which the old man, or boy, proceeds to sit on.

A little Googling corroborated my own distaste. “The Giving Tree” ranks high on both “favorite” and “least favorite” lists of children’s books, and is the subject of many online invectives. One blog post, “Why I Hate The Giving Tree by Shel Silverstein,” argues that the book encourages selfishness, narcissism, and codependency. Unsurprisingly, perhaps, environmental activists rue the boy’s pillaging of the tree and, by extension, the environment. William Cole, who turned down the manuscript when he was an editor at Simon & Schuster (Silverstein took it to Harper & Row), was troubled by its portrayal of parenthood: “My interpretation is that that was one dum-dum of a tree, giving everything and expecting nothing in return.” More recently, the children’s-book author Laurel Snyder said, “When you give a new mother ten copies of ‘The Giving Tree,’ it does send a message to the mother that we are supposed to be this person.”

Still, it’s difficult to know whether Silverstein, who died of a heart attack in 1999, after keeping out of the public eye for more than two decades, meant for us to read the book so conclusively. His biography and body of work suggest a subtler, and, in the end, perhaps an even more troubling, way of looking at it.

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Silverstein detested stories with happy endings. As he once put it, “The child asks, ‘Why don’t I have this happiness thing you’re telling me about?’” His own up-by-the-bootstraps childhood was marked by insecurity and self-doubt. Born in 1930 on the northwest side of Chicago, Sheldon Allan Silverstein grew up in a second-story apartment crammed with relatives. His parents, an immigrant father from Eastern Europe and a Chicago-born mother, opened an unsuccessful bakery on the heels of the Great Depression. Though Silverstein’s mother encouraged his early knack for drawing, his father made it clear that he was expected to join the flailing family business. But Silverstein couldn’t sit still. He was a distracted student, who may have also suffered from dyslexia (at fifteen, he misspelled his middle name on his Social Security application). As Lisa Rogak writes in “A Boy Named Shel,” an engaging 2011 biography of the man, “His attention span ran from nil to nonexistent.”

Silverstein discovered his passion for drawing early, and it became his refuge from his increasingly wrathful father. After a few unsuccessful attempts at college—he never graduated, explaining, “I didn’t get laid much and I didn’t learn much. Those are the two worst things that can happen to a guy”—Silverstein’s listlessness and love of cartoons found an unexpected outlet in the military, which he joined in 1953, serving on the newspaper of a troopship in Japan. His break came three years later when, discharged and unemployed, he visited the offices of a fledgling magazine for men and met its editor, himself an avid cartoonist: Hugh Hefner.

So began Silverstein’s long association with Playboy, where he published not only cartoons and illustrations but also ongoing travelogues from such places as Tokyo, Paris, and Moscow, and became a regular fixture at the seedily infamous Playboy Mansion. By Rogak’s count, he bedded hundreds, if not thousands, of women. He was raggedly attractive (though not particularly handsome): his beard full, his brows furrowed, his half smile gap-toothed, his hair long (later he was completely bald). He liked to wear pirate shirts and a pair of shiny corduroys that, according to a female friend, “made him look like a filing cabinet.” During those Playboy years, Silverstein shuttled back and forth between Chicago and downtown New York; he frequented folk clubs and began making his own music—scribbling away songs on the back of cocktail napkins and tablecloths, performing folk and jazz numbers in a low, gravelly voice.

He was wildly prolific and prolifically wild. On a visit to Denmark, Silverstein signed on as the vocalist of a group called Papa Bue’s Bearded Viking New Orleans Danish Jazz Band. He was the mastermind behind Johnny Cash’s Grammy-winning song “A Boy Named Sue.” He palled around with Norman Mailer and Dustin Hoffman, and reportedly advised a young Bob Dylan on lyrics for what turned out to be “Blood on the Tracks.” “He was our own personal beatnik,” his friend, the actress Lois Nettleton, tells Rogak. Silverstein himself once remarked of his itinerant lifestyle, “Comfortable shoes and the freedom to leave are the two most important things in life.”

As becomes clear from reading Rogak’s biography, Silverstein never intended to write or draw for children. He was often impatient around kids and, Rogak claims, “made no secret of the contempt he felt” for most children’s books. “Hell, a kid’s already scared of being small and insignificant,” he once said. “So what does E. B. White give them? A mouse who’s afraid of being flushed down the toilet or rolled up in a window shade and a spider who’s getting ready to die.” But writing kids’ books was the complete opposite of the work he was doing for Playboy and, maybe for that reason, and with the prodding of a savvy editor, he decided to try his hand at it.

The result was a classic Silversteinian burst of productivity: in 1964 alone, he published three children’s books and one book for adults. Among them was “The Giving Tree,” whose breakaway success caught by surprise not only his publishers, who had printed a modest run of seven thousand copies, but also Silverstein himself, who claimed it had no message. Sales of “The Giving Tree” doubled every year in the decade following its publication; they have since topped five million copies worldwide. But Silverstein was continually asked to defend the book, and this seems to have sapped his energy. “It’s just a relationship between two people; one gives and the other takes,” he would often repeat. It would take him another decade to complete his next children’s book, the fiercely imagined poetry collection “Where the Sidewalk Ends,” and, by 1975, he had almost entirely stopped talking to the press. (Silverstein never married and never wanted to have kids. But circumstances changed the year he turned forty, when one of his former Mansion “playmates” gave birth to a daughter; in 1982, the girl, Shoshanna, died of a brain aneurysm at age eleven, a tragedy from which Silverstein is said to have never recovered. Two years later, a son, Matthew, was born.)