10 of the Best Shel Silverstein Poems Everyone Should Read

By Dr Oliver Tearle (Loughborough University)

Shel Silverstein (1930-99) was a popular American poet, cartoonist, musician, singer-songwriter, and man of many artistic talents. His most enduring poems are those which he wrote for younger readers. Given how popular his poems for children became, the story of how he came to write children’s poetry is somewhat surprising.

Indeed, he hadn’t ever given the idea any thought until a friend suggested that he should do a children’s book. The result was a string of popular books for young readers, including Where the Sidewalk Ends in 1974 (his first book of children’s poems) and A Light in the Attic (1981). He even wrote one of Johnny Cash’s best-known songs: Silverstein won a Grammy for ‘A Boy Named Sue’ in 1970.

Silverstein was a prolific children’s author and wrote many poems for youngsters, so what are his very best poems? Below, we pick ten of his finest. If this selection whets your appetite, we recommend getting hold of what is perhaps his finest book, Where the Sidewalk Ends, which also contains his wonderful drawings.

1. ‘Sick’.

Let’s begin with one of the best-known, and best-loved, Shel Silverstein poems, about a topic many children can relate to: not wanting to go to school. Peggy Ann McKay, the little girl in the poem, tells her parents that she cannot possibly go to school because she is sick – and she promptly lists all of her various ailments, which range from the unlikely (her belly button caving in) to the trivial (a hangnail).

Of course, the first rule of bunking off school is to make your supposed illness convincing, but trying too hard to come up with a long list of potential afflictions only makes it more suspicious. Thankfully, there’s an unexpected development at the end of this poem, which saves Peggy Ann from school after all!

2. ‘Monsters I’ve Met’.

This is one of the shortest poems on this list, but it’s a classic. The poem takes the ideas commonly associated with monsters of various kinds – that ghosts haunt people, devils try to get hold of your soul, vampires want to suck the blood of human beings – and bathetically brings these monsters down to earth for comic effect.

The last two lines are wonderfully judged, and the poem is funny, fun, and witty all at once – all in just eight lines of verse.

3. ‘Messy Room’.

Like ‘Sick’, this is another poem which pulls the characteristic Shel Silverstein trick of containing a sudden twist in the last few lines. The speaker is complaining about how untidy someone’s room is. The details they begin by enumerating include underwear hanging from a lamp and a sweater thrown carelessly on the floor.

But the poem becomes more and more comical as it develops, utilising another trademark Silverstein feature: the list. Once we get to the lizard named Ed which is asleep on the bed, we realise this is indeed a very messy room – but whose is it?

4. ‘Snowball’.

This is another eight-line Silverstein gem. If the story of Raymond Briggs’ The Snowman is too sad and upsetting for you, here’s a little poem that might serve as the comic equivalent to that tragic childhood tale: the speaker makes a snowball and likes it so much they decide to keep it as a pet.

But when they fashion some pyjamas and a pillow for it, and the snowball goes to bed … yes, another twist, though perhaps you can see this one coming before the funny final line …

In many ways, Shel Silverstein can be regarded as a kind of American Roger McGough (another children’s poet who’s also a musician), and this poem suggests an affinity between the two poets more clearly than some other Silverstein poem.

5. ‘Mr Grumpledump’s Song’.

Mr Grumpledump, as his name perhaps suggests, hates everything – or at least, seems to. Everything is wrong, because everything in the world is ‘too’ something: days are too long, the sunshine is too hot for him, and the moon is too high.

Some of his complaints are understandable and relatable – the ground being too dusty, for instance, or his shoes being too tight – while others reveal him to be a complete misery-guts: complaining that other people are too happy, for example (no chance of that with Mr Grumpledump himself!), or that clouds are too fluffy.


The rhythm of this poem, and the list-like structure – recalls Dorothy Parker’s light verse, but the poem is quintessential Shel Silverstein.

6. ‘Whatif’.

Was there ever a better light children’s poem about anxiety and worry than this one? Many of us entertain self-doubt from time to time, and Silverstein’s talent here was to give these doubts concrete form: these ‘whatifs’ crawl into the speaker’s ear like insects, and become the tangible manifestation of those ‘voices in the head’ so many of us have heard which eat away at our happiness and self-confidence.

7. ‘The Giving Tree’.

One of the longer poems on this list, ‘The Giving Tree’ is also one of Silverstein’s most beloved. It’s a narrative poem about a (female) tree which loved a little boy. The boy, in return, loved the tree, but as he grew up, he spent more and more time away from the tree, but whenever he returned, the tree always did her best to provide the boy with what he desired: apples to sell for money, for instance.

The book the poem gives its name to is one of Silverstein’s biggest-selling works and has attracted a range of critical interpretations: some critics and reviewers regard it as a religious parable, while others view it as carrying an environmentalist message.

8. ‘Dirty Face’.

Some of Silverstein’s most celebrated poems are about the playful mischievousness of young children played off against the strict and joyless finger-wagging of adults (parents, teachers).

This poem is a prime example. It contains two speakers: the first (an adult) asks the child how they came to end up with such a dirty face, and the child lists all the things they have been up to. As ever with Silverstein, these range from the usual and expected (crawling around in the dirt) to the downright outlandish (finding a lost silver mine).

9. ‘Falling Up’.

This short poem also gives its name to one of Silverstein’s poetry collections. Here we find the usual order of things inverted in a fun and exciting way: the poem begins normally enough with the speaker tripping over their shoelace, but then they fall upwards instead of down.

They effectively fly up past the treetops and the mountains and high into the sky, until they grow dizzy and … well, in a way that recalls Ogden Nash, there’s some more clever wordplay in the closing line.

10. ‘Where the Sidewalk Ends’.

Where better to conclude this pick of the greatest Shel Silverstein poems than where the sidewalk ends, that magic, hidden space between the path and the road?

Indeed, this is probably the best-known of all of Shel Silverstein’s poems. Published in 1974, it describes a secret other world which lies between the sidewalk and the street: a world which children know how to find, where things are somewhat different from our world.

Chalk arrows children have drawn on the sidewalk direct other would-be travellers to this enchanted land – a land where the wind is as cool and fresh as peppermint, and the mysterious ‘moon-bird’ resides. We discuss this poem at greater length in a separate post.

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