Shel Silverstein wrote and drew some of the most loved children's poetry books in America, including Where the Sidewalk Ends and The Giving Tree. For years he lived aboard a houseboat called the Evil Eye, a converted barge tied up on Sausalito's Liberty Dock, and he also kept homes on Martha's Vineyard, in Key West, and in Greenwich Village. Before he found his young readers he spent years drawing cartoons for Playboy, an adult magazine, and he also wrote hit songs for other performers, including A Boy Named Sue for Johnny Cash, winning two Grammy Awards along the way. In his later years he refused interviews and avoided cameras, letting his work speak for itself. He kept writing and drawing until he died in Key West, Florida, in 1999.
Quotes
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Academy of American Poets biography — gives his birth date as September 25, 1930 and death date as May 10, 1999, with a list of his major poetry collections.
Baltimore Sun's 1999 obituary — confirms he drew Playboy cartoons for years before/during his children's-book career, his homes on Martha's Vineyard, Key West, and Greenwich Village, and that he refused interviews and avoided cameras late in life.
Sausalito Historical Society column — confirms Silverstein lived aboard a converted balloon barge named the Evil Eye on Liberty Dock, part of the bohemian houseboat waterfront he discovered on a magazine assignment.
Added 3 Sept 2026 · claude-sonnet-5
How this life story was put together
Put together from the sources above. The dates and details haven’t been checked against them yet.