Sunday Pages: "Where The Sidewalk Ends"

A poem by Shel Silverstein

Dear Reader,

Where The Sidewalk Ends was published on November 20, 1974—exactly one week after my second birthday (and exactly five weeks before my third Christmas). Thus did Shel Silverstein’s children’s book enter the zeitgeist just as my own inchoate consciousness was snapping into focus.

I distinctly remember reading some of the Silverstein poems from early elementary school—first grade, if memory serves—and being especially taken by the one about the kid trading his dollar for two shining quarters “because two is more than one.” It was in third grade, at an assembly in the gym, as some sixth graders, arrayed on risers, were belting out “The Unicorn,” a silly Silverstein ditty, when I realized, to my horror, that I could not clearly see the face of my friend’s older brother as he merrily sang about green alligators and long-necked geese, humpty-backed camels and chimpanzees. Everyone on the risers was a bit blurry, like an impressionist painting. A few weeks later, I started wearing glasses.

So I have always been aware of Shel Silverstein, who, in my mind, occupies the same lofty stratum as Dr. Seuss: unassailable, holier than holy, most high. The saints of our godless era are the beloved writer-illustrators of rhyming children’s books. To say anything bad about them is tantamount to blasphemy. It’s almost like these works were handed down to Moses on Mount Sinai, who immediately passed them off to the editors at Harper Row. How could the authors be real people?

But Shel Silverstein was very real. And his foray into writing and illustrating children’s books was, in the context of his prolific and multifaceted career, a lark—a whimsical sideline he had to be coaxed and cajoled to do. He was a songwriter, who penned tunes for the likes of Johnny Cash and Loretta Lynn and Marianne Faithful (whose gorgeous rendition of Silverstein’s “The Ballad of Lucy Jordan” is hauntingly good). He wrote dozens—scores—of one-act plays, including one with [checks notes] David Mamet. And he produced humorous cartoons for Playboy magazine from 1957 well into the 1970s. Not your typical children’s book author career path!

Jeff Kinney makes fun of this in one of his Diary of a Wimpy Kid books. Greg Heffley, the eponymous wimpy-kid diarist, reveals that he had been traumatized by the gigantic author photo of Shel Silverstein on the back of the book jacket of The Giving Tree. Silverstein, he writes, “looks more like a burglar or a pirate than a guy who should be writing books for kids.

“Dad must have known that picture kind of freaked me out, because one night right after I got out of bed, Dad said, ‘If you get out of bed again tonight, you’ll probably run into Shel Silverstein in the hallway.’”

The first time I read this out loud to my son, I laughed so hard I crossed over to tears:

The photo on the back cover of my copy of Where The Sidewalk Ends shows a less piratical but still vaguely creepy Silverstein. His bald pate gleams in the sunlight, his right eye masked in shadow. He holds the neck of his acoustic guitar. The look on his face is seductive. His left leg is crossed over his right, and in the foreground, smack-dab in the middle of the rectangular photo, his bare left foot flexes towards us.

“Shel Silverstein is the author of The Giving Tree and many other books of prose and poetry,” the short bio beneath the photo reads. “He also wrote songs, drew cartoons, sang, played the guitar, and loved to have a good time.” That last part is, I believe, a nod to his reputation as the Casanova of Children’s Lit. In interviews, Silverstein laments girls not being interested in him when he was a young man, and he seems to have spent the subsequent years making up for lost time. The guy had game.

I expect that the MAGA censors find Shel Silverstein the paragon of wokeness—I mean, “Hug O’War?” Come on!—but reading through the interviews he gave before he stopped giving them, I wonder how “woke” he actually was IRL. He was born in 1930, well before the war, and his worldview, while certainly liberal for 1974, was perhaps a bit old-fashioned for 2025. This is, after all, the guy who wrote “A Boy Named Sue” and spent a lot of nights hanging out with Hugh Hefner at the Playboy Mansion. He was 68 when he died, in May of 1999, and I wonder if, had he lived longer, his politics would have drifted rightward, as did his former writing partner David Mamet’s.

The point is, there was a darkness to Shel Silverstein. I detect it most acutely in the book’s titular poem, which seems to be conveying some kind of ancient wisdom.

The consensus is that “Where The Sidewalk Ends” is a poem about passing through childhood, full of magic and imagination, to the dull drudgery of grown-up life. The poet calls for a return to the youthful spirit and equates adulthood with factory smoke and macadam.

Certainly it can be read that way. But the lines are more cryptic than that. It begins:

There is a place where the sidewalk ends
And before the street begins,

We tend to think of this as a linear path: after walking down the sidewalk, there is a break, and then comes the street. In this poem, it seems to symbolize childhood (sidewalk) leading to adulthood (street). But logically, the “place where the sidewalk ends and before the street begins” is the little strip of grass between sidewalk and street. This “place” is just as long as the cement and the pavement. It exists in parallel—like a separate dimension.

The next four lines describe this post-sidewalk landscape:

And there the grass grows soft and white,
And there the sun burns crimson bright,
And there the moon-bird rests from his flight
To cool in the peppermint wind.

Commentators tend to regard these lines as some sort of ode to childhood imagination. But none of these descriptors strike me as positive. That it smells like peppermint doesn’t change the fact that the place is hot and dry and populated by a strange and possibly savage wingéd creature. This seems like a bad acid trip. But it is preferable to the sooty Dickensian cityscape, where the narrator is currently rallying interest in his quixotic pilgrimage:

Let us leave this place where the smoke blows black
And the dark street winds and bends.
Past the pits where the asphalt flowers grow

This doesn’t sound like particularly fun time:

We shall walk with a walk that is measured and slow
And watch where the chalk-white arrows go
To the place where the sidewalk ends.

Why, if they are marching towards a place of happiness and light, would they not hurry? Why, if they are emulating the impulsivity of childhood, must they pace in rhythm? He repeats the part about “a walk that is measured and slow,” emphasizing its significance. When do we walk that way? At a funeral procession.

Silverstein concludes:

And we’ll go where the chalk-white arrows go,
For the children, they mark, and the children, they know,
The place where the sidewalk ends.

I always dug the part about the “chalk-white arrows.” This suggests a system of hobo symbols, chalky glyphs that only those in the know can decipher. Once you understand what to look for, you see what you need to see.

But: Why do the children know what the grown-ups don’t? Isn’t wisdom acquired rather than lost? Or is it that children have retained their innocence, and innocence is required to know the way? Is it that they are unafraid to tell the truth? My best guess is, this means that we should abandon logic and reason (which come with age and knowledge and experience) in favor of intuition (which we are born with but which is inevitably corrupted by external forces). Thus the “chalk-white arrows” show us how to trust our inner judgment.

The journey will ultimately lead to the street. Silverstein makes that clear in the first two lines. The “place” is an airlock, a freeport, a DMZ between two defined spaces. The sidewalk exists, he suggests, to lead us to this place, and the goal is to arrive at the end of the line—but slowly, slowly, slowly.

If I am to trust my intuition, as Silverstein seems to be telling me to do, my sense is that the place where the sidewalk ends is terrifying. It is a place of fear. I mean, the cover of the book shows the sidewalk ending at an abyss!

This is why my spine shivers when I read this poem, and not any of the others in the book. I see where this is headed. I see that it is scary. But I also recognize that, come what may, we must confront our fears head on, coolly and calmly, measured and slow.

The moon-bird is just as afraid of us as we are of it.

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ICYMI

I had Silverstein on the brain because of the lovely children’s book Rosanna Arquette read on Friday’s episode of The Five 8:

On Wednesday, another fantastic episode of The Five 8 1/2, with Nadine Smith and Lisa Graves:

And if you hate that cruel Nazi weirdo Stephen Miller—author of so much of Trump’s anti-immigration woe—please share this:

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Happy Mother’s Day!