The son of Nathan Silverstein and Helen Silverstein, Sheldon Alan Silverstein grew up with a sister, Peggy, in Chicago. Lacking in the usual social skills—academic excellence, athletic prowess, or the ability to dance—he was a loner at Roosevelt High School, where he began to draw and write, and independently developed his own unique style. After graduation, he briefly attended the University of Illinois and the Chicago Academy of Fine Arts before enrolling at the Chicago College of Performing Arts at Roosevelt University. Drafted into the U.S. Army in 1953, Silverstein served overseas in Japan and Korea, where he learned to play guitar, write songs, and sing, and where he was employed drawing cartoons for the military publication Pacific Stars and Stripes. After leaving the service in the mid-1950’s, he returned to Chicago, where he contributed cartoons to Look, Sports Illustrated, and other periodicals, especially Playboy magazine, where his work appeared frequently for more than forty years.

In the late 1950’s, Silverstein began writing, playing, and recording music. His first album, Hairy Jazz (1959), included several original songs and his interpretations of jazz standards. He followed up with several additional albums of original music, and his novelty songs—including “The Unicorn,” “Boa Constrictor,” and “Yes, Mr. Rogers”—were covered by such artists as the Irish Rovers, Dr. Hook, and Bobby Bare.

Silverstein entered the children’s literary market in 1963 with the publication of Uncle Shelby’s Story of Lafcadio: The Lion Who Shot Back, which featured his eloquent drawings. He quickly capitalized on the modest success of his first effort with another juvenile prose work, The Giving Tree (1964), and the same year, he published his first book of verse for children, Uncle Shelby’s Giraffe and a Half. Throughout the 1960’s and 1970’s, Silverstein continued producing children’s stories and poems, cartoons for adult markets, and music that he or others recorded. In the 1980’s, he primarily concentrated on drama, writing a number of short adult plays—such as The Lady or the Tiger Show (pr. 1981), Wild Life (pr. 1983), The Happy Hour (pr. 1985), Wash and Dry (pr. 1986), and The Devil and Billy Markham (pr. 1989)—and collaborated with playwright-director David Mamet on the screenplay of the film Things Change (1988). Late in life, Silverstein returned to writing poetry for adults and children.

Silverstein had a daughter, Shoshanna, with Susan Hastings, in 1970. After Hastings’s death in 1975, the girl went to live with grandparents; she died at the age of eleven of a brain aneurysm. In 1983, he had a son, Matt, with Sarah Spencer. Silverstein died of a heart attack in Key West, Florida, probably on May 8, 1999, though his body was not discovered for two days. He was sixty-eight years old.