Where to Start with Shel Silverstein

Shel Silverstein (1930-1999) was an American poet, singer-songwriter, cartoonist, screenwriter, and author of children’s books. Born in Chicago, he began his career as a cartoonist for Stars and Stripes while serving in the US Army in Japan and Korea, then became a regular contributor to Playboy magazine. His first children’s book, Lafcadio, the Lion Who Shot Back, appeared in 1963, but it was his poetry collections that made him a household name. Where the Sidewalk Ends (1974) became the bestselling children’s poetry book of all time, selling over four and a half million copies. His recording of the poems won a Grammy Award for Best Recording for Children. He also wrote The Giving Tree (1964), one of the most widely read picture books in American history, and the country music hit “A Boy Named Sue” for Johnny Cash. Silverstein was famously private, rarely granting interviews and refusing to allow his photo on his book jackets for years.

Where the Sidewalk Ends

Shel Silverstein · 176 pages · 1974 · Easy

Themes: children's poetry, humor, nonsense verse, illustrations

The bestselling children’s poetry book ever written, and the one that turned millions of kids into poetry readers without them even noticing. Shel Silverstein’s 1974 collection contains over 130 poems and drawings that range from the gleefully absurd to the quietly moving, all delivered in a voice that never talks down to its audience.

Why Start Here

Where the Sidewalk Ends is the purest expression of what Silverstein does best. His later collections are wonderful, but this is where the voice crystallized: funny, anarchic, tender when you least expect it, and always rhythmically precise. The book established a new kind of children’s poetry that was neither nursery rhyme nor educational verse, but something wild and free that belonged entirely to kids.

Starting here gives you the poems that became cultural touchstones. “Sick” (with its epic list of fabricated illnesses to avoid school), “Boa Constrictor” (the poem that eats itself), and “Sarah Cynthia Sylvia Stout Would Not Take the Garbage Out” have been memorized by millions of children across five decades. These poems work because Silverstein understood that the best way to reach a child is not to aim low, but to aim true.

What to Expect

A 176-page hardcover with Silverstein’s own pen-and-ink illustrations on nearly every page. The poems are short, rarely longer than a page, and most rhyme in simple, memorable patterns. His Grammy-winning audio recording of these poems is worth seeking out as well, as Silverstein’s gruff, warm delivery adds another dimension to the work.

Where the Sidewalk Ends →

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