Cartoons '' travelogues, collected in 2007 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! 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 Pennsylvania
naturist community, the
Chicago White Sox training camp, San Francisco's Haight-Ashbury, 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..." A cartoon he made during the 1950s was featured on the cover of his next cartoon collection, titled ''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." His musical output included a large catalog of songs; a number of them were hits for other artists, such as the rock group
Dr. Hook & the Medicine Show. 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"", "Freaker's Ball", "
Sylvia's Mother", "The Things I Didn't Say" and "Don't Give a Dose to the One You Love Most". Silverstein had a popular following on
Dr. Demento's radio show. Among his better-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 1962 song "
Boa Constrictor", sung by a person who is being swallowed by a snake. The latter song was recorded by the folk group
Peter, Paul and Mary, and also by
Johnny Cash for his 1966 album
Everybody Loves a Nut. One of Silverstein's last musical projects was
Old Dogs, a 1998 album with 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). 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 who recorded Silverstein's songs include
the Brothers Four,
Andrew Bird,
My Morning Jacket and
Bobby Bare Jr. Theater 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 on 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, Husband and Wife, 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 named The Spectrum Players, 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 a character of an emcee 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. On November 29, 2022, a revival of Shel Silverstein's "Lafcadio: The Lion Who Shot Back" opened at the Gishen Hall of the Niavaran Cultural Center in Tehran, Iran. The performance was reviewed in the Tehran Times on December 15, 2022. The review said "But is a famous, successful, and admired lion a happy lion? Or is he a lion at all? Told and drawn with wit and gusto. Shel Silverstein's modern fable speaks not only to children but to us all!"
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"),
Postcards from the Edge ("I'm Checkin' Out"), 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"). ==Views on his own writing==