While Silverstein was primarily known for his work as a children's author, he did venture into songwriting. He wrote and recorded several albums of folk and country music, often performing his songs himself. His songs often had a humorous and satirical edge, reflecting his unique style of storytelling.
Some of Silverstein's well-known songs include "A Boy Named Sue," which became a hit single for Johnny Cash in 1969, and "The Ballad of Lucy Jordan," which was recorded by Dr. Hook & the Medicine Show. He also collaborated with other musicians and wrote songs for artists like Loretta Lynn and Bobby Bare.
Silverstein's songwriting showcased his ability to weave clever lyrics and engaging narratives, similar to his writing for children's books. While his music career wasn't as extensive as his literary contributions, it demonstrated his versatility as an artist and his talent for entertaining audiences across different mediums.