The Great Gatsby
F. Scott Fitzgerald (1925)
“A devastating critique of the American Dream, written by a man who lived it and lost everything.”
Essay Questions & Food for Thought
30questions designed to challenge assumptions and provoke original thinking. These can't be answered from a summary — you need the actual text.
Why does Fitzgerald make Nick Carraway the narrator instead of telling Gatsby's story directly? What do we lose — and gain — from seeing Gatsby only through Nick's eyes?
Tom Buchanan casually references white supremacist literature ('The Rise of the Colored Empires'). Why does Fitzgerald include this, and why does no character challenge Tom on it?
Gatsby says 'Can't repeat the past? Why of course you can!' Is he wrong? Does the novel ultimately agree with him, mock him, or grieve for him?
Nick tells us Gatsby 'turned out all right at the end.' Given that Gatsby dies alone in a pool, abandoned by everyone including Daisy — what does Nick mean? Is Nick reliable here?
Why does Fitzgerald set the 'valley of ashes' between East/West Egg and New York? What is its literal and symbolic function?
Daisy's voice is described as 'full of money.' Why is this more devastating than calling her greedy, shallow, or corrupt?
If Gatsby had gotten Daisy back — truly, permanently — would he have been happy? Use textual evidence.
Fitzgerald published The Great Gatsby in 1925 but set it in 1922. Why the three-year gap? What does writing about the very recent past allow that writing in real-time wouldn't?
The novel mentions Black characters exactly twice — in passing. Is this a failure of Fitzgerald's imagination, a deliberate choice, or a reflection of Nick's perspective?
Compare Gatsby's parties to modern social media. In what ways is Instagram the new green light?
Why does almost no one come to Gatsby's funeral? What does this say about the nature of his relationships — and about wealth-based social networks?
Tom and Gatsby both lie constantly. Why does the novel treat Gatsby's lies as romantic and Tom's as repulsive? Is this fair?
Jordan Baker cheated in a golf tournament. Why does Fitzgerald include this detail? How does it connect to the novel's larger treatment of honesty and performance?
The eyes of Doctor T.J. Eckleburg on the billboard — George Wilson calls them 'the eyes of God.' Is he right? Is there a moral authority in this novel, or just a billboard?
Fitzgerald was broke and considered a failure when he died in 1940. Gatsby was rescued from obscurity by WWII Armed Services Editions. How does knowing this change your reading of the novel's themes about legacy and time?
Why does Nick describe himself as 'one of the few honest people I have ever known'? Is he? Find three moments where Nick is clearly not being honest — with others or himself.
Myrtle Wilson tries to perform wealth — the apartment, the affected speech, the dog. Why does Fitzgerald make this performance so obviously doomed?
How would this novel be different if it were set in 2026? What would Gatsby's equivalent be — crypto? Tech? Influencing? What would the green light become?
The novel takes place over one summer. Why is the compressed timeline important? How does it affect the pacing and the sense of inevitability?
Fitzgerald uses color systematically — green (hope), gold/yellow (wealth/corruption), white (false purity), grey (moral wasteland). Choose one color and trace it through the entire novel.
Is Gatsby a tragic hero in the classical sense? Does he have a hamartia (fatal flaw)? Or is the system itself the antagonist?
Why does Fitzgerald have Gatsby show Daisy his shirts — and why does she cry? This is one of the most analyzed scenes in American literature. What's actually happening emotionally?
Nick claims the East 'haunted' him after that summer. But he also admits he was 'within and without, simultaneously enchanted and repelled.' Is Nick a victim or a willing participant?
How does knowing that Fitzgerald modeled Gatsby partly on a real bootlegger (Max Gerlach, who actually said 'old sport') change or deepen your reading?
Compare The Great Gatsby to Death of a Salesman. Both dissect the American Dream. How are Gatsby and Willy Loman similar and different? Which critique is more effective, and why?
Fitzgerald originally wanted to title the novel 'Trimalchio in West Egg' (after a character in Petronius's Satyricon who throws lavish parties to cover his low origins). Would that have been a better title? Why or why not?
Water appears throughout the novel — the Sound between East and West Egg, the rain during Gatsby and Daisy's reunion, Gatsby's death in the pool. What is water doing symbolically?
If you removed every scene where characters drink alcohol, how much of the novel would remain? What does this tell you about the role of alcohol in the social world Fitzgerald depicts?
Read the last page of the novel aloud. How does the sound of the language — the rhythm, the vowels, the pacing — mirror the meaning? What does Fitzgerald's prose DO that the meaning alone can't?
The Great Gatsby entered the public domain in 2021, spawning unauthorized sequels, reimaginings, and adaptations. Does the novel gain or lose something when anyone can rewrite it? What would Gatsby think about that?