Born and raised in Chicago, Illinois, Silverstein briefly attended university before being drafted into the United States Army.

His songs have been recorded and popularized by a wide range of other acts including Tompall Glaser, The Irish Rovers, Dr. Hook & the Medicine Show and Marianne Faithfull.

[10] 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.

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, Fire Island, Mexico, London, Paris, Spain and Africa.

[11] 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.

[13] 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.

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" titled "Father of a Boy Named Sue", which is less known, but he performed the song on television on The Johnny Cash Show.

[11] He wrote many of the songs performed by Bobby Bare, including "Rosalie's Good Eats Café", "The Mermaid", "The Winner", "Daddy What If", "Warm and Free", and "Tequila Sheila".

Silverstein's "The Ballad of Lucy Jordan", first recorded by Dr. Hook in 1975, was re-recorded by Lee Hazlewood (1976), Marianne Faithfull (1979), Belinda Carlisle (1996), and Bobby Bare (2005) and later featured in the films Montenegro and Thelma & Louise.

He wrote "In the Hills of Shiloh", a poignant song about the aftermath of the American Civil War, 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.

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."

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.

[17] A longtime friend of singer-songwriter Pat Dailey, Silverstein collaborated with him on the posthumously released Underwater Land album (2002).

Other artists who recorded Silverstein's songs include the Brothers Four, Andrew Bird, My Morning Jacket and Bobby Bare Jr.[19][20] 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.

[22] 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.

[24] 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:[25] 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.

[27] 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.

Other credits include the shorts De boom die gaf (based on his novel) and Lafcadio: The Lion Who Shot Back.

[29] 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?

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 an interview with Publishers Weekly in 1975, 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.

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?

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.

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.

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.

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.