Most people know Shel Silverstein as the beloved author of The Giving Tree and Where the Sidewalk Ends, but fewer realize that he was also an incredibly talented songwriter and musician.
Before becoming famous as a children’s author, Silverstein built a remarkable career in the music world. His songs were recorded by some of the biggest names in country, rock, and folk music — including Johnny Cash, Loretta Lynn, and Dr. Hook & the Medicine Show.
Let’s take a closer look at the songs Shel Silverstein wrote and the artists who brought his clever, heartfelt, and often humorous lyrics to life.
“A Boy Named Sue” – Johnny Cash
Perhaps the most famous song Shel Silverstein ever wrote is “A Boy Named Sue.”
This witty, storytelling song became a massive hit for Johnny Cash after he performed it live at San Quentin Prison in 1969. The song tells the story of a man with an unusual name — Sue — who sets out to find and confront the father who named him that.
Silverstein’s humorous but meaningful lyrics made the song an instant classic, and it became one of Cash’s signature hits. It even won a Grammy Award for Best Country Song in 1970.
“The Cover of ‘Rolling Stone’” – Dr. Hook & the Medicine Show
Another one of Silverstein’s best-known songs is “The Cover of ‘Rolling Stone’,” written for Dr. Hook & the Medicine Show in 1972.
The track humorously tells the story of a struggling rock band dreaming of fame — specifically, of appearing on the cover of Rolling Stone magazine. The song became a hit and actually earned the band that very honor; they were featured on the cover shortly after its release.
This song perfectly captures Silverstein’s mix of wit, irony, and playful social commentary.
“Sylvia’s Mother” – Dr. Hook & the Medicine Show
Silverstein also wrote the emotional ballad “Sylvia’s Mother,” another major hit for Dr. Hook.
Unlike his more humorous works, this song is deeply sentimental. It tells the story of a man trying to call his former lover, Sylvia, only to be stopped by her mother, who tells him that Sylvia is leaving to start a new life.
Released in 1972, it reached the Top 5 in the U.S. and No. 1 in several countries, showing Silverstein’s versatility as a songwriter who could move seamlessly between comedy and heartbreak.
“The Unicorn” – The Irish Rovers
One of Silverstein’s earlier hits as a songwriter was “The Unicorn,” recorded by The Irish Rovers in 1967.
This whimsical folk song tells the story of how the unicorn missed Noah’s Ark and, as a result, was never seen again. The song became a beloved children’s tune and remains one of The Irish Rovers’ most popular recordings to this day.
The track showcased Silverstein’s ability to write imaginative, storytelling lyrics that appealed to both kids and adults. This theme carried over into his later work as a children’s author.
“One’s on the Way” – Loretta Lynn
In 1971, country legend Loretta Lynn turned Shel Silverstein’s song “One’s on the Way” into a hit.
The song humorously depicts the life of a busy housewife in Topeka, Kansas, juggling family duties and pregnancy while hearing about glamorous celebrities living carefree lives.
Its sharp humor and real-world relatability made it one of Loretta Lynn’s most loved tracks — and proved that Silverstein had a unique understanding of women’s perspectives, despite his rough-and-tumble image.
“25 Minutes to Go” – Johnny Cash
Silverstein wrote another song recorded by Johnny Cash called “25 Minutes to Go.”
This darkly comic tune, often called a “gallows countdown,” describes a prisoner’s final moments before execution. With every verse counting down the minutes, it balances grim humor with social commentary — a combination Silverstein mastered throughout his songwriting career.
“Queen of the Silver Dollar” – Emmylou Harris & Dr. Hook
Another gem from Shel Silverstein’s catalog is “Queen of the Silver Dollar.”
Originally performed by Dr. Hook & the Medicine Show, it was later covered by Emmylou Harris. The song paints a vivid portrait of a barroom queen adored by regulars but longing for a simpler life. Its mix of melancholy and tenderness is classic Silverstein storytelling.
Other Songs You Might Not Know He Wrote
Shel Silverstein’s songwriting career spanned multiple genres and decades. Here are a few more of his notable works:
- “Boa Constrictor” – A humorous children’s song from his poetry collections.
- “Marie Laveau” – A fun country hit for Bobby Bare about the legendary New Orleans voodoo queen.
- “The Ballad of Lucy Jordan” – Later recorded by Marianne Faithfull, telling a haunting story of suburban despair.
- “Freakin’ at the Freakers Ball” – A wild, tongue-in-cheek anthem celebrating counterculture.
- “Daddy What If” – A tender duet written for Bobby Bare and his son.
A Poet with a Guitar
What made Shel Silverstein so unique as a songwriter was his ability to mix humor, honesty, and human emotion in everything he wrote.
Whether he was writing a silly children’s rhyme, a bittersweet country ballad, or a satirical rock song, his words always had heart — and often a clever twist. His songwriting legacy shows that great storytelling doesn’t just belong on the page — it also belongs in a melody.
Final Thoughts
So, what songs did Shel Silverstein write? From A Boy Named Sue to The Cover of ‘Rolling Stone’, Sylvia’s Mother, and One’s on the Way, Silverstein’s lyrics have left a lasting mark on both music and pop culture.
His songs continue to be performed, covered, and cherished — proving that Shel Silverstein wasn’t just a poet for children, but a poet for everyone.