Sheldon Allan Silverstein /ˈsɪlvərstiːn/ (September 25, 1930 – May 10, 1999) was an American writer known for his cartoons, songs, and children’s books. He styled himself as Uncle Shelby in some works. His books have been translated into more than 30 languages and have sold more than 20 million copies. He was the recipient of two Grammy Awards, as well as Golden Globe Award and Academy Award nominations.
Born into a Jewish family, Silverstein grew up in the Logan Square neighborhood of Chicago, attended Roosevelt High School and, later, the University of Illinois, from which he was expelled. He then enrolled in the Chicago Academy of Fine Arts which he was attending when he was drafted into the United States Army. He served in Japan and Korea.
Silverstein began drawing at age seven by tracing the works of Al Capp. He told Publishers Weekly: “When I was a kid—12 to 14, I’d much rather have been a good baseball player or a hit with the girls, but I couldn’t play ball. I couldn’t dance. Luckily, the girls didn’t want me. Not much I could do about that. So I started to draw and to write. I was also lucky that I didn’t have anybody to copy, be impressed by. I had developed my own style; I was creating before I knew there was a Thurber, a Benchley, a Price and a Steinberg. I never saw their work ’til I was around 30. By the time I got to where I was attracting girls, I was already into work, and it was more important to me. Not that I wouldn’t rather make love, but the work has become a habit.”
He was first published in the Roosevelt Torch, a student newspaper at Roosevelt University, where he studied English after leaving the Art Institute. During his time in the military, his cartoons were published in Pacific Stars and Stripes, where he had originally been assigned to do layouts and paste-up. His first book, Take Ten, a compilation of his military Take Ten cartoon series, was published by Pacific Stars and Stripes in 1955. He later said his time in college was a waste and would have been better spent traveling around the world meeting people.
After returning to Chicago, Silverstein began submitting cartoons to magazines while also selling hot dogs at Chicago ballparks. His cartoons began appearing in Look, Sports Illustrated and This Week.
Mass-market paperback readers across America were introduced to Silverstein in 1956 when Take Ten was reprinted by Ballantine Books as Grab Your Socks! The edition included a foreword by Bill Mauldin.
In 1957, Silverstein became one of the leading cartoonists in Playboy, which sent him around the world to create an illustrated travel journal with reports from far-flung locales. During the 1950s and 1960s, he produced 23 installments called “Shel Silverstein Visits…” as a feature for Playboy. Employing a sketchbook format with typewriter-styled captions, he documented his own experiences at such locations as a New Jersey naturist community, the Chicago White Sox training camp, San Francisco’s Haight-Ashbury district, Fire Island, Mexico, London, Paris, Spain and Africa. In a Swiss village, he drew himself complaining, “I’ll give them 15 more minutes, and if nobody yodels, I’m going back to the hotel.” These illustrated travel essays were collected by the publisher Fireside in Playboy’s Silverstein Around the World, published in 2007 with a foreword by Hugh Hefner and an introduction by music journalist Mitch Myers.
In a similar vein were his illustrations for John Sack’s Report from Practically Nowhere (1959), a collection of humorous travel vignettes previously appearing in Playboy and other magazines.[
“Now here’s my plan…”
His best-known cartoon of the 1950s was featured on the cover of his next cartoon collection, Now Here’s My Plan: A Book of Futilities, which was published by Simon & Schuster in 1960. Silverstein biographer Lisa Rogak wrote:
The cartoon on the cover that provides the book’s title would turn out to be one of his most famous and often-cited cartoons. In the cartoon, two prisoners are chained to the wall of a prison cell. Both their hands and feet are shackled. One says to the other, “Now here’s my plan.” Silverstein was both fascinated and distressed by the amount of analysis and commentary that almost immediately began to swirl around the cartoon. “A lot of people said it was a very pessimistic cartoon, which I don’t think it is at all,” he said. “There’s a lot of hope even in a hopeless situation. They analyze it and question it. I did this cartoon because I had an idea about a funny situation about two guys.”
Silverstein’s cartoons appeared in issues of Playboy from 1957 through the mid-1970s, and one of his Playboy features was expanded into Uncle Shelby’s ABZ Book (Simon & Schuster, 1961), his first book of new, original material for adults. Because it was unclear whether some of the material was intended for adults or children, the 1985 reprint had a conspicuous cover label.
Views on his own writing
Silverstein’s editor at Harper & Row, Ursula Nordstrom, encouraged Silverstein to write children’s poetry. Silverstein said that he had never studied the poetry of others and had therefore developed his own quirky style, laid back and conversational, occasionally employing profanity and slang. In a 1975 Publishers Weekly interview, he was asked how he came to do children’s books:
“I didn’t,” Shel said, “I never planned to write or draw for kids. It was Tomi Ungerer, a friend of mine, who insisted—practically dragged me, kicking and screaming, into Ursula Nordstrom’s office. And she convinced me that Tomi was right; I could do children’s books.” The relationship between Ursula Nordstrom and Shel Silverstein is mutually rewarding. He considers her a superb editor who knows when to leave an author-illustrator alone. Asked if he would change something he had produced on an editor’s say-so, he answered with a flat “No.” But he added: “Oh, I will take a suggestion for revision. I do eliminate certain things when I’m writing for children if I think only an adult will get the idea. Then I drop it, or save it. But editors messing with content? No.” Had he been surprised by the astronomical record of The Giving Tree, his biggest seller to date and one of the most successful children’s books in years? Another emphatic no. “What I do is good,” he said. “I wouldn’t let it out if I didn’t think it was.” But The Giving Tree, which has been selling steadily since it appeared almost 10 years ago and has been translated into French, is not his own favorite among his books. “I like Uncle Shelby’s ABZ, A Giraffe and a Half, and Lafcadio, the Lion Who Shot Back—I think I like that one the most.”
Otto Penzler, in his crime anthology Murder for Revenge (1998), commented on Silverstein’s versatility:
The phrase “Renaissance man” tends to get overused these days, but apply it to Shel Silverstein and it practically begins to seem inadequate. Not only has he produced with seeming ease country music hits and popular songs, but he’s been equally successful at turning his hand to poetry, short stories, plays, and children’s books. Moreover, his whimsically hip fables, beloved by readers of all ages, have made him a stalwart of bestseller lists. A Light in the Attic, most remarkably, showed the kind of staying power on the New York Times chart—two years, to be precise—that most of the biggest names (John Grisham, Stephen King and Michael Crichton) have never equaled with their blockbusters. His unmistakable illustrative style is another crucial element to his appeal. Just as no writer sounds like Shel, no other artist’s vision is as delightfully, sophisticatingly cockeyed. One can only marvel that he makes the time to respond so kindly to his friends’ requests. In the following work, let’s be glad he did. Drawing on his characteristic passion for list making, he shows how the deed is not just in the wish but in the sublimation.
his anthology was the second in a series, which also included Murder for Love (1996) and Murder and Obsession (1999). All three anthologies included Silverstein contributions. He did not really care to conform to any sort of norm, but he did want to leave his mark for others to be inspired by, as he told Publishers Weekly:
I would hope that people, no matter what age, would find something to identify with in my books, pick up one and experience a personal sense of discovery. That’s great. I think that if you’re a creative person, you should just go about your business, do your work and not care about how it’s received. I never read reviews because if you believe the good ones you have to believe the bad ones too. Not that I don’t care about success. I do, but only because it lets me do what I want. I was always prepared for success but that means that I have to be prepared for failure too. I have an ego, I have ideas, I want to be articulate, to communicate but in my own way. People who say they create only for themselves and don’t care if they are published… I hate to hear talk like that. If it’s good, it’s too good not to share. That’s the way I feel about my work. So I’ll keep on communicating, but only my way. Lots of things I won’t do. I won’t go on television because who am I talking to? Johnny Carson? The camera? Twenty million people I can’t see? Uh-uh. And I won’t give any more interviews.
Silverstein studied briefly at Chicago College of Performing Arts at Roosevelt University. His musical output included a large catalog of songs; a number of them were hits for other artists, most notably the rock group Dr. Hook & The Medicine Show. He wrote Tompall Glaser’s highest-charting solo single, “Put Another Log on the Fire”, “One’s on the Way” and “Hey Loretta” (both hits for Loretta Lynn, in 1971 and 1973 respectively), and “25 Minutes to Go”, sung by Johnny Cash, about a man on Death Row with each line counting down one minute closer. Silverstein also wrote one of Johnny Cash’s best known hits, “A Boy Named Sue” as well as “The Unicorn”, first recorded by Silverstein himself in 1962 but better known in its version by The Irish Rovers. Other songs co-written by Silverstein include “The Taker” written with Kris Kristofferson and recorded by Waylon Jennings, and a sequel to “A Boy Named Sue” called “Father of a Boy Named Sue”, which is less known, but he performed the song on television on The Johnny Cash Show. He also penned a song entitled “F**k ’em” which is lesser known and contained a reference to “f**k kids.”
He wrote the lyrics and music for most of the Dr. Hook & the Medicine Show songs on their first few albums, including “The Cover of ‘Rolling Stone’”, “Freakin’ at the Freakers’ Ball,” “Sylvia’s Mother”, “The Things I Didn’t Say” and a cautionary song about venereal disease, “Don’t Give a Dose to the One You Love Most”. He wrote many of the songs performed by Bobby Bare, including “Rosalie’s Good Eats Café”, “The Mermaid”, “The Winner”, “Warm and Free”, and “Tequila Sheila”. He co-wrote with Baxter Taylor “Marie Laveau”, for which the songwriters received a 1975 BMI Award. The third album by Tompall Glaser contained eight songs by Silverstein and three by Silverstein and others.
Silverstein’s “The Ballad of Lucy Jordan”, first recorded by Dr. Hook in 1975, was re-recorded by Marianne Faithfull (1979), Belinda Carlisle (1996), and Bobby Bare (2005) and later featured in the films Montenegro and Thelma & Louise. “Queen of the Silver Dollar” was first recorded by Dr. Hook on their 1972 album Sloppy Seconds, and later by Doyle Holly (on his 1973 album Doyle Holly), Barbi Benton (on her 1974 album Barbi Doll), Emmylou Harris (on her 1975 album Pieces of the Sky) and Dave & Sugar (on their 1976 album Dave & Sugar).
Silverstein composed original music for several films and displayed a musical versatility in these projects, playing guitar, piano, saxophone and trombone. He wrote “In the Hills of Shiloh”, a poignant song about the aftermath of the Civil War, which was recorded by The New Christy Minstrels, Judy Collins, Bobby Bare and others. The soundtrack of the 1970 film Ned Kelly features Silverstein songs performed by Waylon Jennings, Kris Kristofferson and others. He also co-wrote with Waylon the song ‘A Long Time Ago’.
In addition, Silverstein wrote “Hey Nelly Nelly,” a 1960s-era folk song recorded by Judy Collins.
Silverstein had a popular following on Dr. Demento’s radio show. Among his best-known comedy songs were “Sarah Cynthia Sylvia Stout (Would Not Take The Garbage Out)”, “The Smoke-Off” (a tale of a contest to determine who could roll—or smoke—marijuana joints faster), “I Got Stoned and I Missed It” and “Stacy Brown Got Two.” He wrote “The Father of a Boy Named Sue”, in which he tells the story from the original song from the father’s point of view, and the 1962 song “Boa Constrictor”, sung by a person who is being swallowed by a snake (recorded by the folk group Peter, Paul, and Mary) also recorded by Johnny Cash for his 1966 album Everybody Loves A Nut although it is now better known as a children’s playground chant.
One of the last musical projects Silverstein completed in his lifetime was Old Dogs, a 1998 one-off album and supergroup which performed songs about getting old, all of which Silverstein wrote or co-wrote.
A longtime friend of singer-songwriter Pat Dailey, Silverstein collaborated with him on the posthumously released Underwater Land album (2002). It contains 17 children’s songs written and produced by Silverstein and sung by Dailey (with Silverstein joining him on a few tracks). The album features art by Silverstein.
He was a friend of Chicago songwriter Steve Goodman, for whom he wrote the final verse of “What Have You Done For Me Lately?” (refusing a songwriting credit for his contribution). Goodman also recorded Silverstein’s “Three-Legged Man”, as did Ray Stevens.
In 2010, Bobby Bare and his son Bobby Bare Jr produced a CD called Twistable, Turnable Man: A Musical Tribute to the Songs of Shel Silverstein which was released on Sugar Hill Records. Other artists recording Silverstein songs include the Brothers Four, Andrew Bird, My Morning Jacket and Bobby Bare, Jr.
In January 1959, Look, Charlie: A Short History of the Pratfall was a chaotic off-Broadway comedy staged by Silverstein, Jean Shepherd and Herb Gardner at New York’s Orpheum Theatre on Second Avenue in the Lower East Side. Silverstein went on to write more than 100 one-act plays. The Lady or the Tiger Show (1981) and Remember Crazy Zelda? (1984) were produced in New York. The Devil and Billy Markham, published in Playboy in 1979, was later adapted into a solo one-act play that debuted on a double bill with Mamet’s Bobby Gould in Hell (1989) with Dr. Hook vocalist Dennis Locorriere narrating. In 1990, Silverstein’s one-act modernized version of Hamlet starred Melvin Van Peebles playing all the roles. Karen Kohlhaas directed An Adult Evening of Shel Silverstein, produced by New York’s Atlantic Theater Company in September 2001 with a variety of short sketches:
- “One Tennis Shoe”—Harvey claims his wife is becoming a bag lady.
- “Bus Stop”—Irwin stands on a corner with a “bus stop” sign.
- “Going Once”—A woman auctions herself.
- “The Best Daddy”—Lisa’s daddy shot the pony he got for her birthday.
- “The Lifeboat is Sinking”—Jen and Sherwin play a game of Who-Would-You-Save-If—the family was drowning.
- “Smile”—Bender plans to punish the man responsible for the phrase “Have a nice day”.
- “Watch and Dry”—Marianne discovers her laundry has not been cleaned.
- “Thinking Up a New Name for the Act”—Pete thinks “meat and potatoes” is the perfect name for a vaudeville act.
- “Buy One, Get One Free”—Hookers offer a golden opportunity.
- “Blind Willie and the Talking Dog”—Blind Willie’s talking dog argues they could profit from his talent.
A production of An Adult Evening of Shel Silverstein was produced by a Hofstra University theater group called The Spectrum Players, which was founded by Francis Ford Coppola in 1959. The production used a “victorian sailors on shore leave watching a play” aesthetic and used live rag-time and an MC character not in the script to transition between pieces. The production was directed by Richard Traub of Chicago and starred several of Hofstra’s most promising young actors: Nick Pacifico, Amanda Mac, Mike Quattrone, Ross Greenberg, Chelsea Lando, Allie Rightmeyer, and Paolo Perez as the MC.
In December 2001, Shel’s Shorts was produced in repertory as two separate evenings under the titles Signs of Trouble and Shel Shocked by the Market Theater in Cambridge, Massachusetts. Signs of Trouble was directed by Wesley Savick, and Shel Shocked was directed by Larry Coen.
TV and film
Silverstein co-wrote the screenplay for Things Change with David Mamet. He also wrote several stories for the TV movie Free to Be… You and Me. Silverstein wrote and narrated an animated short of The Giving Tree, first produced in 1973; a remake based on Silverstein’s original screenplay but without his narration was released in 2015 by director Brian Brose. Other credits include the shorts De boom die gaf (based on his novel) and Lafcadio: The Lion Who Shot Back.
His songs have been used in many TV shows and movies, including Almost Famous (“The Cover of ‘Rolling Stone’”), Thelma & Louise (“The Ballad Of Lucy Jordan”) and Coal Miner’s Daughter (“One’s on the Way”), as well as the Dustin Hoffman film Who Is Harry Kellerman and Why Is He Saying Those Terrible Things About Me? (“Bunky and Lucille”, “Last Morning”).
Silverstein’s “A Boy Named Sue” won a 1970 Grammy. He was nominated for an Oscar and a Golden Globe Award for his song “I’m Checkin’ Out” in the film Postcards from the Edge.
Together with longtime friend and producer Ron Haffkine, he released “Where the Sidewalk Ends” on cassette in 1983, and as an LP phonograph record in 1984, winning the 1984 Grammy Award for Best Recording For Children.
He was posthumously inducted into the Nashville Songwriters Hall of Fame in 2002. Silverstein was inducted into the Chicago Literary Hall of Fame in 2014.
Silverstein lived on a Sausalito houseboat between c.1967 to about 1975, and additionally he owned homes in Greenwich Village, Martha’s Vineyard, and Key West.
Silverstein never married. He did, according to the 2007 biography A Boy Named Shel, sleep with “hundreds, perhaps thousands of women.” He was also a frequent presence at Hugh Hefner’s Playboy Mansion and Playboy Clubs.
He had one daughter, Shoshanna Jordan Hastings, born June 30, 1970, with Susan Taylor Hastings of Sausalito, California, whom he reportedly met at the Playboy Mansion. Susan died on June 29, 1975, one day before Shoshanna’s fifth birthday, and Shoshanna went to live with her uncle and aunt in their Baltimore home. Shoshanna died April 24, 1982, at age 11, of a cerebral aneurysm. The book A Light in the Attic is dedicated to her.
He also had a son named Matthew, born November 10, 1984, with Sarah Spencer of Key West, Florida; Sarah drove a tourist trackless train and inspired Shel’s song “The Great Conch Train Robbery.”
On May 10, 1999, Silverstein died at age 68 of a heart attack in Key West, Florida and was subsequently buried in Westlawn Cemetery in Norridge, Illinois.
On June 25, 2019, The New York Times Magazine listed Shel Silverstein among hundreds of artists whose material was reportedly destroyed in the 2008 Universal fire.