Rethinking The Great Gatsby: How I Learned to Love (and Teach) a Classic

Most high school English teachers would consider what I’m about to say complete sacrilegious: I didn’t like reading The Great Gatsby in high school, and for many years, I really didn’t enjoy teaching it.

However, over time, I’ve had a total change of heart. As I’ve worked to make Fitzgerald’s Jazz Age novel more accessible, hands-on, and relevant for my high school juniors, I’ve developed a deep appreciation for the text. More importantly, my students are actually enjoying it, too!

If you are looking to refresh your Gatsby unit, here are the classroom-tested strategies, activities, and paired texts that transformed this novel from a drag into a highlight of our year.

1. Get Students Out of Their Seats: Evidence Anticipation Walk

There aren’t always enough opportunities for movement in a secondary English classroom. To launch the unit, I get students moving and thinking on Day 1 with a Text Evidence Detective Activity.

• The Setup: I typed, printed, and laminated 30 compelling sentences directly from the novel.
• The Activity: Every student receives at least one sentence strip. They step into the role of “detectives” and walk around the room sharing their sentences with classmates, logging nine additional quotes on a tracking sheet.
• The Reflection: Once back in their seats, students analyze their collection of “evidence” to make predictions about the plot, characters, and mood. We wrap up with a lively whole-class discussion of their theories before they even open Chapter 1.

2. Model the Struggle: First-Page Think-Aloud

Fitzgerald’s syntax and elevated style can intimidate reluctant readers right out of the gate. To build confidence early, I distribute a standalone copy of the very first page for a targeted close read.

I ask students to annotate for clues about our narrator, Nick Carraway. To start, I model a think-aloud with line one:

“In my younger and more vulnerable years…”

I stop and explain to the class: “This immediately tells me Nick is reflecting on his past from an older, more experienced perspective. He’s positioning himself as someone who has gained wisdom over time.” Modeling how to decipher word choice helps lower their anxiety for the rest of the chapter.

3. Expand the Narrative: Powerful Literary Pairings

Pairing short, impactful companion texts helps students see Gatsby as part of a broader cultural conversation about privilege, gender roles, and the American Dream.

Essential Poetry & Drama

• “Richard Cory” by Edwin Arlington Robinson: This is arguably the ultimate poetic companion. Both Gatsby and Richard Cory project an image of effortless wealth and status while hiding profound internal isolation.
• A Raisin in the Sun by Lorraine Hansberry: Mama’s famous line to Walter—”Once upon a time freedom used to be life—now it’s money. I guess the world really do change”—directly critiques the shift from moral/existential freedom to pure materialism. It offers a crucial counter-narrative to Gatsby’s 1920s consumerism.
• “The World Is Too Much With Us” by William Wordsworth: Wordsworth’s Romantic critique of industrialization (“Getting and spending, we lay waste our powers”) mirrors Fitzgerald’s depiction of Jazz Age moral decay and the bleakness of the Valley of Ashes.

Short Stories & Contemporary Choices

• “The Devil and Tom Walker” by Washington Irving: A classic tale of selling one’s soul for financial gain. Gatsby’s shady connections to Meyer Wolfsheim parallel Tom Walker’s literal bargain with Old Scratch.
• “The Story of an Hour” by Kate Chopin & “The Yellow Wallpaper” by Charlotte Perkins Gilman: These short stories illuminate the gilded cages upper-class women inhabited. Placing Daisy Buchanan or Myrtle Wilson alongside these narrators reframes Daisy’s shallow cynicism (“a beautiful little fool”) as a survival mechanism in a patriarchal world.
• The House on Mango Street by Sandra Cisneros: Esperanza’s search for identity and social mobility offers a modern, intersectional contrast to Jay Gatsby’s pursuit of status.

4. Multi-Modal Engagement: Graphic Novels & TED Talks

To reach visual learners, English Language Learners, and reluctant readers, I love incorporating alternative media.

• The Graphic Novel Adaptation: Using graphic novel excerpts side-by-side with Fitzgerald’s prose works wonders for struggling readers who need visual context for setting and character expressions.
• Curated TED Talks: We often pause our reading to watch and discuss real-world psychology and social issues. (Check out my detailed post on TED Talks to Pair With American Literature “Does Money Make You Mean?”, “Less Stuff, More Happiness,” and “The Difference Between Healthy and Unhealthy Love.”)

5. Pass the Mic: Fishbowl Roundtable Discussions

Once students build confidence around Chapters 5 and 6, I transition from teacher-led instruction to student-led discussions using a Fishbowl (Inside/Outside Circle) format.

Warm-Up & Rehearsal: Students complete a quick-write prompt, review a discussion rubric, and pair up to rehearse their ideas using their chapter notes.

• The Fishbowl: We arrange our desks into an inner and outer circle. The inner circle leads an open dialogue about the chapter for 10–15 minutes while the outer circle actively listens and takes peer notes.
• The Swap: We rotate the groups so everyone sits in the inner circle.
• Reflection: Students return to their seats and write a quick self-assessment on their participation and insight.

Read more about how students take more ownership for their learning in this blog post with a full description of Roundtable Discussion.

6. Structure the Prep: Numbered Heads Together

Early in the novel, when students are still getting used to the text, I use a cooperative learning strategy called Numbered Heads Together to scaffold our chapter discussions.

1. Arrange students into heterogeneous groups of 3 to 5 and assign each member a number (1 through 5).
2. Provide a set of text-dependent questions for the chapter.
3. Groups work together to craft strong answers, ensuring everyone at the table understands the material.
4. When it’s time to share out, I call a random combination: “All Number 3s, please stand up to answer Question 2.”

Because students don’t know who will be called on, every group member stays accountable. It also gives shy or struggling students a low-stakes opportunity to rehearse their answers with peers before speaking to the whole class. (Read my complete guide to Livening Up Reading Discussion for more reading discussion tips!)

7. Keep Them Accountable: Low-Stakes Reading Checks

Let’s be honest: students won’t understand The Great Gatsby if they aren’t reading it. To keep everyone on track without creating an overwhelming grading pile, I use Socrative(though you can easily substitute whatever tool or app works best for your students, like Quizizz or Google Forms) for quick reading checks at the start of class.

I create 3 to 5 simple multiple-choice or true/false recall questions. Students respond on their devices (or paper), giving me instant data reports. It immediately reveals who completed the reading and who might need extra comprehension support before we dive into analytical discussions.

8. Put the Text on Trial: The Chapter 7 Accident Investigation

After the climax in Chapter 7, we pause for a close-reading CSI-style investigation of the car crash that kills Myrtle Wilson.

Students step into specific roles—such as CSI Unit Worker, Medical Examiner, Police Officer, Witness, Prosecutor, or Journalist—to re-read the chapter and catalog text evidence. They analyze the timeline, driver visibility, and impaired driving laws of the era to determine legal fault. Each student must write a formal rationale defending who should be charged with the crime based strictly on textual evidence.

9. The Finale: First-Person Character Essays & A Roaring ’20s Party

Instead of giving a standard multiple-choice unit exam, I assign a hybrid summative assessment.

Each student selects a character from the novel and writes a first-person analytical essay. They must adopt their character’s voice while supporting their claims with direct quotes from the novel.

To ensure high rigor, the essay must include a paragraph explaining how their character’s choices connect to one of Fitzgerald’s central themes.

The Celebration!

We celebrate finishing the novel with a Roaring ’20s Character Party! Students dress in era-appropriate attire (or carry a prop representing their chosen character) and stay in character as they mingle and interview one another. I often invite administrators or guest classes to drop by and ask our “characters” questions. It brings the unit to an unforgettable, high-energy close.

Over to You!

It took some trial and error, but shifting The Great Gatsby from a passive reading assignment to an active, evidence-based experience turned it into one of my absolute favorite units to teach.

What are your favorite activities, strategies, or paired texts for teaching Gatsby? I’d love to hear your ideas in the comments below!