What was Shel Silverstein’s Net Worth?

Shel Silverstein was an American writer, humorist, cartoonist, songwriter, musician, and playwright who had a net worth of $20 million at the time of his death. Shel Silverstein is best known as the author of such children’s books as “The Giving Tree” and “Where the Sidewalk Ends.” He also penned the satirical alphabet book “Uncle Shelby’s ABZ Book.”

Shel Silverstein penned a number of hit songs for other musicians, perhaps most notably Loretta Lynn and Johnny Cash. He wrote Loretta Lynn’s 1971 #1 single “One’s on the Way” and her 1973 hit “Hey Loretta.”

As a songwriter, Silverstein achieved his greatest commercial success with “A Boy Named Sue,” which was a hit song for Johnny Cash in 1969.

Shel Silverstein passed away on May 10, 1999 at 68 years old of a heart attack.

Early Life and Education

Shel Silverstein was born on September 25, 1930 in Chicago, Illinois to a Jewish family. He was educated at Roosevelt High School, and then briefly at the University of Illinois Urbana-Champaign until he was expelled. Silverstein subsequently attended the Chicago Academy of Fine Arts and Roosevelt University. While still a student, he was drafted into the US Army, and ended up serving in Japan and Korea. In the military, Silverstein had some of his cartoons published in the Pacific Stars and Stripes newspaper.

Career Beginnings

Returning to Chicago after his military service, Silverstein started submitting his cartoons to various magazines while selling hot dogs at local ballparks. Soon, his cartoons were appearing in such publications as Sports Illustrated and This Week. In 1956, Silverstein’s compilation book “Grab Your Socks!” was published in paperback. The following year, he became a leading cartoonist for Playboy magazine, which sent him around the globe to create an illustrated travel journal. This resulted in the Playboy feature “Shel Silverstein Visits…,” containing 23 installments that were printed throughout the 50s and 60s.

(Photo by Alice Ochs/Michael Ochs Archives/Getty Images)


Silverstein rose to his greatest renown in the 60s. Kicking off the decade, he released the cartoon collection “Now Here’s My Plan” and the satirical alphabet book “Uncle Shelby’s ABZ Book.” His first children’s book, “Uncle Shelby’s Story of Lafcadio: The Lion Who Shot Back,” was published in 1963. Silverstein subsequently released four books in 1964, the most famous of which is “The Giving Tree,” a controversial tale about the relationship between a boy and an apple tree. Another release that year was “Don’t Bump the Glump!,” Silverstein’s first book of verse and his only work to contain illustrations in full color.

In 1974, Silverstein released another of his most famous works, the children’s poetry collection “Where the Sidewalk Ends.” This was followed two years later by the children’s picture book “The Missing Piece.” Closing out the decade, Silverstein released “Different Dances.” His next title was the 1981 poetry collection “A Light in the Attic,” which became a bestseller. Silverstein’s third and final poetry collection was 1996’s “Falling Up,” which was also his final one to be published during his life. Three further books were published posthumously: 2005’s “Runny Babbit,” 2011’s “Every Thing On It,” and 2017’s “Runny Babbit Returns.”

Music Career

As a musician and songwriter, Silverstein created a wide range of songs, many of which became hits for other artists. Among them were Tompall Glaser’s “Put Another Log on the Fire”; Loretta Lynn’s “One’s on the Way” and “Hey Loretta”; the Irish Rovers’ “The Unicorn”; and Johnny Cash’s “25 Minutes to Go” and “A Boy Named Sue.” The latter song became both Silverstein’s and Cash’s biggest commercial hit when it reached number two on the Billboard Hot 100 in the US.

Silverstein’s most prolific and longstanding music collaboration was with the rock band Dr. Hook & the Medicine Show. He wrote the music and lyrics for most of the songs on the group’s first few albums, including such tracks as “Sylvia’s Mother,” “The Things I Didn’t Say,” and “The Ballad of Lucy Jordan.” Silverstein also wrote many songs performed by Bobby Bare, including “The Mermaid” and “Tequila Sheila.” His musical output also included songs recorded by Judy Collins, Waylon Jennings, Pat Dailey, and Peter, Paul and Mary, among other artists. Additionally, in the 70s, Silverstein composed music for the films “Ned Kelly” and “Who is Harry Kellerman and Why is He Saying Those Terrible Things About Me?” Later, he wrote the Oscar-nominated song “I’m Checkin’ Out” from the 1990 film “Postcards from the Edge.”

Theater Career

In early 1959, Silverstein staged an off-Broadway comedy play called “Look, Charlie: A Short History of the Pratfall.” Later on, he became a prolific playwright, writing over 100 one-act plays over the decades. His credits included “The Lady or the Tiger Show,” “Remember Crazy Zelda?,” and “The Devil and Billy Markham,” which was adapted from his story published in Playboy.

Personal Life and Death

From about 1967 to 1975, Silverstein resided on a houseboat in Sausalito, California. Additionally, he owned homes in Key West, Florida; Martha’s Vineyard, Massachusetts; and Greenwich Village in New York City. Although Silverstein never married, he was reported to have been highly promiscuous, and was a frequent guest at Hugh Hefner’s Playboy properties. At the Playboy Mansion, he met Susan Hastings, with whom he had a daughter named Shoshanna in 1970. Hastings died in 1975, and Shoshanna passed away from an aneurysm in 1982. Later, Silverstein began dating Sarah Spencer; they had a son named Matthew in 1984.

In May of 1999, Silverstein died from a heart attack at his home in Key West. He was 68 years of age.

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