Sheldon Allan Silverstein, professionally known as Shel Silverstein, was an award-winning writer, poet, screenwriter, cartoonist, and singer.
He is recognized for writing children’s books and even styled himself as ‘Uncle Shelby’ in some of his works. His published books have sold more than 20 million copies and have been translated into more than 30 different languages.
He was also nominated for a Golden Globe Award and an Oscar Award for his song “I’m Checkin’ Out” and was awarded two Grammy Awards for his works, including “A Boy Named Sue” and “Where the Sidewalk Ends.”
He was a man of rare gifts, with a strong sense of wisdom and humor. It’s no wonder that much of what he has said and written has become quite famous over the years.
Below is a collection of Shel Silverstein’s most memorable quotes about life, art, friendship, and everything in between—words that continue to inspire, amuse, and move readers around the globe.
Fun fact: Shel Silverstein originally wanted to be a baseball player, but when that didn’t pan out, he picked up a pen instead—and the world’s been grateful ever since.
Table of Contents
Shel Silverstein Quotes on Life & Wisdom
Shel Silverstein’s reflections on life invite us to embrace uncertainty, stay curious, and seek joy in the journey.
Listen to the mustn’ts, child. Listen to the don’ts. Listen to the shouldn’ts, the impossibles, the won’ts. Listen to the never haves, then listen close to me… Anything can happen, child. Anything can be.
– Where the Sidewalk Ends (1974)
This beloved passage reminds us to question limits and trust in possibility, no matter what others say.
There are no happy endings. Endings are the saddest part,
So just give me a happy middle
And a very happy start.
– Every Thing On It (2011, posthumous collection)
Silverstein urges us to savor the journey, not just the outcome.
If the track is tough and the hill is rough,
THINKING you can just ain’t enough!
– Where the Sidewalk Ends (1974)
Determination and action are what get us up the hill—Silverstein believed in hope backed by effort.
How much good inside a day? Depends how good you live ‘em.
– A Light in the Attic (1981)
A gentle nudge to make each day meaningful through our choices.
Shel Silverstein Quotes on Creativity & Imagination
Silverstein’s world is one where anything is possible, and imagination is the key.
Draw a crazy picture,
Write a nutty poem,
Sing a mumble-gumble song,
Whistle through your comb.
Do a loony-goony dance
‘Cross the kitchen floor,
Put something silly in the world
That ain’t been there before.
– A Light in the Attic (1981)
Here, Silverstein empowers us to create, no matter how odd it seems—creativity is its own reward.
If you are a dreamer, come in.
If you are a dreamer, a wisher, a liar,
A hope-er, a pray-er, a magic bean buyer…
If you’re a pretender, come sit by my fire
For we have some flax-golden tales to spin.
– Where the Sidewalk Ends (1974)
A call to all dreamers to join in and celebrate the beauty of storytelling and make-believe.
Anything is possible. Anything can be.
– Where the Sidewalk Ends (1974)
Silverstein’s central message: the only limits are those we accept.
Shel Silverstein Quotes on Love & Friendship
Through his stories, Silverstein captured the heartache and hope of giving and receiving love.
Once there was a tree…and she loved a little boy.
– The Giving Tree (1964)
Perhaps his most iconic line—simple but profound, it reminds us of unconditional love.
I will not play at tug o’ war.
I’d rather play at hug o’ war,
Where everyone hugs
Instead of tugs,
Where everyone giggles
And rolls on the rug.
– Where the Sidewalk Ends (1974)
Silverstein invites us to build a world with more kindness and less conflict.
All the magic I have known
I’ve had to make myself.
– Where the Sidewalk Ends (1974)
An ode to self-reliance and the magic we create with friends and loved ones.
Shel Silverstein Quotes on Childhood & Innocence
No one captured the voice of childhood—joys, fears, and questions—like Silverstein.
Anything can happen, child. Anything can be.
– Where the Sidewalk Ends (1974)
A mantra for young and old alike—never lose your sense of wonder.
Children are…the most honest critics.
They are our only hope for the future.
If the world was crazy, you know what I’d eat?
A big slice of soup and a whole quart of meat.
– Where the Sidewalk Ends (1974)
A playful look at how children view the world—Silverstein saw value in the silly and strange.
Shel Silverstein Quotes on Dreams & Possibility
Silverstein never stopped encouraging us to dream—no matter our age.
If you want to find magic, you have to look for it.
– A Light in the Attic (1981)
A gentle reminder to keep seeking wonder, even when life gets busy.
The World Through Silverstein’s Pen
Shel Silverstein’s legacy endures because his words welcome us—child or adult—into a world where the impossible seems possible, where kindness and creativity rule, and where the heart always has a place at the table.
Whether you need encouragement, a moment of laughter, or a reminder to dream, his quotes continue to inspire and delight.
