Podcast Summary: Old School with Shilo Brooks

Episode: What ‘The Great Gatsby’ Taught Fareed Zakaria About America

Date: November 13, 2025
Host: Shilo Brooks
Guest: Fareed Zakaria

Episode Overview

This episode explores how F. Scott Fitzgerald’s "The Great Gatsby" helped Fareed Zakaria, a noted journalist and political commentator, make sense of America as an immigrant and intellectual. Shilo Brooks and Zakaria discuss the enduring themes of the novel—including reinvention, the American Dream, social class, and the pitfalls of modern life—and why literature like Gatsby remains vital. The conversation delves into the personal and cultural resonance of the book, examining how it shaped Zakaria’s worldview and how its lessons hold up in today’s society.

Key Discussion Points & Insights

1. The Value of a Liberal Education

• Zakaria describes his broad educational background: history, philosophy, political theory, and how a liberal education fosters creative and synthetic thinking (03:22).
  • Quote: “A liberal education really means not a trade education… It’s a broad, wide ranging education… The idea behind it is to help train your mind to think.” – Fareed Zakaria [03:22]
• He contrasts the American emphasis on thinking broadly with other systems focused on test-taking (04:54).
  • Quote: “Our [Singaporean] education system teaches people how to take tests. Your education teaches people how to think.” – Singapore Minister (as recalled by Zakaria) [05:14]

2. First Encounters with American Literature

• Zakaria grew up in India, where most of the curriculum centered on British writers. College in the US introduced him to American literature (07:04).
• "The Great Gatsby" was a way for Zakaria to understand both America and his own immigrant experience.
  • Quote: “It made sense of America, it made sense of Yale, it made sense of my immigrant experience in a very profound way.” – Fareed Zakaria [07:41]

3. ‘Gatsby’ as an American Cultural Mirror

• The novel’s central tension is between the hope and disappointment that define the American Dream.
  • Zakaria references his PhD advisor Sam Huntington: “It is not a lie. It is a disappointment. But it can only be a disappointment because it is a hope. That is Gatsby.” [10:13]
• Gatsby’s story is one of self-invention and reinvention—an immigrant and American motif (16:07).
  • Quote: “Every immigrant is engaging in an act of reinvention when they come to this country… But that’s actually also very much part of the American story.” – Fareed Zakaria [16:07]

4. Character Analyses: Gatsby, Nick, Tom, and Daisy

• Gatsby’s allure is his relentless optimism and drive for reinvention; he embodies the American self-made myth.
  • Zakaria: “He gets so enamored… it becomes almost all surface and the parties and the glamour… The funeral… it was all facade… I didn’t actually know the guy. I just went to his parties. I loved the music, the glamour, the champagne, but I didn’t know him.” [17:48]
• Gatsby’s failure, despite his success, is seen as a warning about the emptiness of pure ambition and the limits of social mobility.
• Nick Carraway is dissected as both a moral center and a complicit observer. He admires Gatsby’s passion, yet cannot entirely excuse his flaws.
  • Brooks: “Nick...can be called the moral center of the novel. But… he's also complicit in some of the degrading, more sort of morally vulgar behavior that Tom is engaged in.” [25:28]
• Tom and Daisy Buchanan represent old money, moral carelessness, and the persistent social barriers.
  • Zakaria: “They were careless people, Tom and Daisy, and they smash things up and then they retreat to their vast carelessness and let others clean up their mess.” [30:53]

5. Wealth, Success, and American Identity

• The discussion highlights America’s unique reverence for wealth and the tendency to conflate financial achievement with wisdom or virtue (27:31).
  • Zakaria: “It’s the only country in which if you become rich people assume you are also wise.” [27:31]
• Both Gatsby and Myrtle, striving for a higher class, end up dead; the old money class emerges unscathed.
  • Brooks: “The characters who strive most for the top end up in the most tragic circumstances in The Great Gatsby.” [29:46]

6. The Jazz Age as Backdrop

• Brooks provides historical and cultural context to the Jazz Age—the era of exuberance, moral fluidity, and cultural rebellion in which the novel is set (32:00).
• The period’s excess and liberation serve as both backdrop and symbol for the novel’s moral questions.

7. Love, Obsession, and the Limits of Romance

• Both agree Gatsby is not a love story, but rather a study of obsession, ambition, and longing.
  • Zakaria: “The Great Gatsby is not a love story. It is not about love...It’s about obsession, about longing, about the American Dream, about self-invention.” [35:48]
• Brooks suggests the novel is, in fact, a romance with America and its ideals—not with individual people.

8. Why ‘Gatsby’ Endures

• The story’s canonization is explained—failures at publication, revival by WWII GIs, and Lionel Trilling’s influential reframing of the novel as emblematic of American ideals (36:35).
• Fitzgerald’s lyricism and the novel’s accessibility make it continually relevant:
  • Zakaria reads the famous last lines, tying them to perennial American themes of striving and nostalgia:
    • “So we beat on, boats against the current, borne back ceaselessly into the past.” – Fitzgerald, read by Zakaria [40:53]
• The novel’s focus on the loneliness and hollowness of modern, liberal, individualistic life remains urgent in an age of social media and superficial glamour (47:51).
  • Zakaria: “We are still grappling with that same problem… liberalism… leaves a kind of hollowness inside. It leaves a hole in the heart, and we’re still trying to fill that.” [48:36]

9. Personal Reflections and Changing Meanings

• Zakaria shares how the book’s impact has deepened with his life experience. The lessons about wealth, success, and happiness have become more real but the essential insights remain as they did when he was young (44:10).
• Both discuss how great literature can immunize readers—especially young men—against the temptations of superficial success (49:40).

Notable Quotes & Memorable Moments

On Liberal Education:

• Zakaria: “A liberal education… is to help train your mind to think, and train your mind to think broadly and widely...” [03:22]

On America and the Dream:

• Zakaria: “It is not a lie. It is a disappointment. But it can only be a disappointment because it is a hope. That is Gatsby.” [10:20]
• Zakaria (Trilling paraphrase): “Gatsby is… the quintessential American novel because it is the story of the American dream of promise, but of unfulfilled promise.” [10:43]

On Gatsby’s Passion:

• Zakaria (quoting Gatsby): “He had thrown himself into it with a creative passion… No amount of fire or freshness can challenge what a man will store in his ghostly heart.” [22:16]

On Social Mobility & Reinvention:

• Zakaria: “You can’t reinvent yourself in the old country… It is only in America that you have this possibility for complete reinvention. And Gatsby embodies that.” [16:07]

On Wealth & Hollowness:

• Zakaria: “He has lots of [glamour], but the central message is actually that… there is a kind of hollowness at the core of all that money.” [28:25]

On Fitzgerald’s Style:

• Zakaria (reading closing lines): “So we beat on, boats against the current, borne back ceaselessly into the past.” [41:19]
• Zakaria: “It’s not just the beauty of the prose but the thought… it encapsulates so much.” [41:45]

Key Timestamps / Segments

• 00:39 – Zakaria’s intellectual upbringing and the power of liberal education
• 06:37 – His first encounter with Fitzgerald and American literature
• 09:42 – Gatsby as the American Dream—and its inevitable disappointment
• 11:31 – Gatsby plot summary
• 15:56 – Gatsby as a symbol of self-invention; the darker side of self-making
• 20:14 – Gatsby’s dual nature: attractiveness and hollowness
• 23:21 – Nick Carraway’s ambiguous morality
• 27:31 – America’s tendency to idolize financial success
• 32:00 – The Jazz Age context
• 35:48 – The novel as a meditation on obsession, not love
• 40:53 – Reading and interpreting the novel’s iconic closing passage
• 44:10 – How the meaning of Gatsby has shifted/persisted for Zakaria
• 47:51 – The novel’s enduring appeal and accessibility
• 49:40 – Great literature as immunization against the “decadent liberalism”
• 52:20 – Lightning round: college courses, books, foreign policy, and journalism
• 59:24 – Zakaria: The dangers of a visual culture and shortform media for journalism and thought

Tone & Language

The tone is erudite but approachable, with moments of humor and warmth. Both Brooks and Zakaria maintain a sense of awe toward Fitzgerald’s prose and a pragmatic realism about American ideals. Their discussion is punctuated by personal anecdotes, literary analysis, and cultural critique, making literary study feel both intellectually serious and intimately relevant.

Conclusion

This episode stands out as a passionate defense of both liberal education and the continuing necessity of close, careful reading of literary classics. Zakaria’s insights, especially as someone for whom Gatsby was a window into America, offer a fresh lens on the novel’s themes of hope, longing, reinvention, and disillusionment. The episode closes with a call for the enduring value of books and deep conversation, both in personal growth and in resisting the superficial distractions of modern culture.