Why I Teach Shel Silverstein to High Schoolers (And What It Means for How We Choose Texts and Mentor Texts)

Three years ago I realized that my poetry unit needed help. While I gushed about the thoughtful symbolism of “Ozymandias” or the elegant simplicity of Gwendolyn Brooks’ “We Real Cool,” I looked out and found far too many worried or blank looks on the faces of my students–looks that spoke to them being lost, indifferent, or both.

So the next year I started my poetry unit with a request that students bring in poems that they love, thinking that these favorite poems would show my students that poetry wasn’t something foreign or beyond them; it was something they already knew and loved. But, as is so often the way in the classroom, things didn’t exactly go as I’d scripted.

What happened was that in two sections of 9th graders, nearly 30 of the 60 students brought in a poem by Shel Silverstein. Volumes of Where the Sidewalk Ends and The Giving Tree populated my desks, and while I have my own fondness for Shel Silverstein, I was at first deeply annoyed by this. Bringing him in felt like a mockery of the class and the assignment. Obviously, “Peanut Butter Sandwich” has no place in a high school–or so it seemed to me at the time.

But I was stuck, so I begrudgingly let each student talk about his/her/their favorite poet, and as I listened to them, it quickly became clear that the vast majority of students who brought in Shel Silverstein weren’t trying to be funny or to make a snarky statement about the class. They brought in his poems because reading them was the last time that they truly connected with poetry or felt that it wasn’t over their heads.

This day was a revelation for me. Up until that point I’d tried all sorts of things to make poetry interesting and accessible to students. I’d tried to lead with poets I considered non-threatening like Emily Dickinson or Langston Hughes, I’d gone to great effort to teach living poets (including Tracy K. Smith, Kaveh Akbar, Nate Marshall, Ada Limon, and Joy Harjo), brought in daily poems, showed amazing slam poems like this, and had my students write plenty of poems of their own.

And yet there was always a fair amount of students who held-out or tuned-out when it came to poetry. They looked at the blazing brilliance of the modern poets or Dickinson’s innovative use of slant rhyme and dashes and they told themselves a sadly common story: that poetry is just too complex, beyond their capabilities, and for other people, not them.

But many remembered Shel Silverstein (or their favorite singer/rapper, which was the other choice for most students) being for them. So, as I listened to students gush Silverstein and their other favorite poets, I decided to toss out my planned lesson and just go with it. Once the class was done sharing, I asked if they wanted to take a closer look at a Silverstein poem on the board. They heartily agreed and several students asked for the poem “Whatif” (see right). I remembered this poem from my own childhood, so I found it and put it on the board, and for the next twenty minutes, I stood amazed as the students dissected it with remarkable precision. They identified the thoughtful use of repetition (namely Whatif, “And,” and question marks) that shows how persistently the “Whatifs” dog the narrator; the basic AABBCC rhyme scheme in the vein of a nursery rhyme that is disrupted in the line “Whatif they start a war?/Whatif my parents get divorce?”–potentially showing the narrator’s fear of her family falling apart; the organization of the poem, which is very thoughtful, with the intensity of the whatifs waxing and waning deliberately to create and release tension; the transition at the end from the whatifs to “Everything seems swell” and how it feels weird and acts as a false volta where the poem should turn but in fact doesn’t; the various dismissed conventions like the spelling of “whatif” that set a tone and make a point; and the theme of childhood worry, which in hindsight is every bit as thoughtful as the themes from the other poets I was sharing.

Even more amazing was that every single student–even those who’d told me they didn’t like poetry–leaned forward, amazed to see this staple of many of their childhoods being revisited on the board in a high school class.

Enthused by this result, I asked for another Silverstein poem, and someone said “Here I Go Down the Circle Road” (see left). I found that and put it on the board, and once again the class instantly began to identify the poetic structures being employed: the interesting use of space and the inclusion of a little drawing of a strange man on the start of a journey, the common and potent symbols like dust or hearts, the lack of punctuation and distinction between capitalized and non-capitalized words, the use of alliteration and puns like “wind,” and the cryptic and in many ways problematic theme that takes some unpacking.

Then I asked for another favorite and a student said Tupac’s short and sweet poem “The Rose that Grew from Concrete” and another student said her favorite song, so we looked a those. Finally, a last student said Emily Dickinson, but by that point the students were hooked; when I put up a Dickinson poem, the students engaged with it in a way that I’d never seen before, and I think leading with Silverstein was likely to thank for this.

By the end of that day, I had a new approach, not just to my poetry unit, but to how I select texts and mentor texts for all of my units. I used to pick texts that I thought the students would like or that would be at the right level for them, maybe Langston Hughes for a poetry unit or David Sedaris for a narrative one.

And while I still use these texts, I also have deliberate spaces for my students to choose texts too. Students help me to choose articles of the week, supplemental texts for all of my units, and mentor texts in nearly every genre. The idea is that when students bring texts that they love for the class to look at alongside the texts I chose, the confluence can create a dramatic increase in engagement, excitement, and outcomes and understanding.

I think there are a lot of potential reasons for this. There is the unexpectedness of analyzing something like Silverstein that generates attention, the element of choice empowers the students and reminds them that we turn the keys of learning together, the inquiry of exploring a new text together is exciting and instructive for both parties, and maybe most importantly, the students help me to find entry points where they feel comfortable and engaged.

This last point–really carefully thinking through the entry points for students–makes me think about a book I am just beginning and loving so far, Planning Powerful Instruction by Jeffrey Wilhelm, Rachel Bear, and Adam Fachler. In explaining the book in a recent article, they say…

Anyone who has ever taught knows this intuitively: We have to capture learners’ interests and emotions, help them see personal connections, and get them invested in the purpose and payoff of learning  before  asking them to do any considerable work towards it.

Jeffrey Wilhelm, Rachel Bear, and Adam Fachler

When it came to poetry and other units, I was often guilty of assuming my students knew or would come to know the purpose and payoffs, and so I often jumped right into the considerable amount of work part. I took the the audible groans from my classes at the start of my poetry unit as givens, not as an opportunity to open a dialogue with them.

Now, the groans have disappeared, thanks in part to me co-conspiring for how to build student comfort, excitement, and value with the best source possible: the students themselves!

Yours in Teaching,



Teachers are busy–too busy–so we need to share with each other. That is why this blog exists. I’ve studied and written about writing instruction and finding balance for over ten years and would love to share what I’ve found with you. Join my mailing list now and I will send you a thoughtful post about teaching and curated reading suggestions each week. As a thank you, you will also receive the first chapter free of my upcoming book Flash Feedback: Responding to Student Writing Better and Faster – Without Burning Out.

3 responses to “Why I Teach Shel Silverstein to High Schoolers (And What It Means for How We Choose Texts and Mentor Texts)”

  1. Honored by your shout out, Matt! Really thoughtful connections and reflections here. And THE GIVING TREE is one of my all-time favorites to teach… to any age!


    1. Thanks, Adam! I absolutely love the book! I even recommended it to a district I work with in Ohio that has since picked it up for their teachers as a resource for some major curriculum changes they are making! And yes, The Giving Tree is a poetic marvel. Seeing it from a teaching lens gave me a new appreciation of what a magician Silverstein is!


  2. […] have used some student-found mentor texts in the past, but generally most of my mentor texts have been ones that were chosen and curated by […]


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