A Classic Summer Read

Summary

Zero to Well-Read – "A Classic Summer Read"

Podcast: Zero to Well-Read
Hosts: Jeff O’Neal, Rebecca Schinsky
Date: May 12, 2026
Episode Theme: The Great Gatsby by F. Scott Fitzgerald

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Episode Overview

This episode of Zero to Well-Read revisits F. Scott Fitzgerald’s "The Great Gatsby," marking the novel's 100th anniversary. Part book club, part irreverent English seminar, hosts Jeff O’Neal and Rebecca Schinsky engage in an in-depth, fresh conversation about the book’s plot, context, language, and modern relevance—“everything you need to know about the books you wish you’d read.” The duo thoughtfully unpacks Gatsby’s continued influence, the novel’s rich sentences, themes of illusion and longing, and its sharp, enduring social critique. The episode is designed for both new readers and those revisiting Gatsby as adults.

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Approach and Purpose of the Podcast

[04:13–11:37]

• Why talk about classics like Gatsby?
  • The show bridges the gap between English class and fun book discussion, without snobbery.
  • "People want to be well-read…they want to know what the big deal is about the books that they feel like they’re supposed to have read." – Rebecca [05:05]
  • To be well-read is to "have a sense of what is going on in the bookish zeitgeist and how we got here." – Rebecca [06:34]
  • Edutainment is the goal, blending facts and fun.
• Nuanced engagement, not hot takes
  • Jeff emphasizes resisting the urge for surface-level "takes" and instead wrestling with a book’s complexity.
  • "We are not take merchants…The book itself is a strata on which we can dance a little bit and have a good time…" – Jeff [07:05]
  • They aim to cultivate “nuanced thinkers” and resist intellectual shortcuts. Reading as “resistance to an intellectual sluggishness.” [13:40]
• The evolving meaning of classics
  • "None of these classics started out old and canonical…all of these works were at one point contemporary." – Jeff [08:15]
  • The podcast revisits these books with modern eyes, bridging literary tradition and the present.
• Format
  • Each episode provides context, plot, analysis, notable passages, and applicability, even for those who haven’t read the book.

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The Great Gatsby: Plot & Themes Recap

[18:18–28:12]

• Plot Summary
  • Nick Carraway, a young Midwesterner, rents a house in West Egg next to the mysterious, wealthy Jay Gatsby, who hosts extravagant parties and fixates on the green light across the water—the home of his lost love, Daisy Buchanan.
  • Daisy is married to Tom, who is abusive and unfaithful; Daisy and Gatsby reignite their old romance with Nick’s help.
  • The narrative crescendos in a sweltering hotel room confrontation—Daisy says she once loved both Tom and Gatsby.
  • Reckless driving after the confrontation leads to Daisy (or Gatsby) accidentally killing Tom’s mistress, Myrtle. Gatsby is murdered by Myrtle’s husband, and dies friendless.
• Themes
  • Longing for the past and unattainable dreams (symbolized by the green light).
  • The American Dream—and who gets access to it.
  • Performance and illusion versus authenticity.
  • Social class and reckless privilege.
  • Moral ambiguity and flawed characters.
• Key quote:
  • "It is a messy summer vibes novel." – Rebecca [21:40]
  • "Crazy Rich Caucasians." – Jeff, joking about alternate titles [23:03]

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Context: Fitzgerald’s Life & The Novel’s Reception

[28:12–38:54]

• Autobiographical echoes
  • Fitzgerald, like Gatsby, aspired to move from Midwestern roots to East Coast glamor. His courtship of Zelda mirrored Gatsby’s quest for Daisy—delayed until he had money.
  • Gatsby’s parties, obsession, and ultimate isolation reflect both the Jazz Age and Fitzgerald’s own struggles.
• Publication history and shifting status
  • Initially, "Gatsby" was not a commercial or critical hit; only posthumously and after its inclusion in WWII military editions did it become a staple American classic.
  • "My God, I am a forgotten man." – Fitzgerald in a letter, 1940 [37:41]
• Critical repositioning
  • Gatsby’s lasting power came less from initial acclaim than cultural adoption and its incorporation into education and popular myth.

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Revisiting Gatsby: Adult & Teenage Readings

[38:54–46:25]

• Returning to Gatsby as adults
  • Both hosts find the book richer, sadder, and more rewarding with age.
  • Rebecca: "News flash: The Great Gatsby is fucking awesome." [44:24]
  • Jeff: “The thing that really strikes me now is how Gatsby’s portrayal of the kind of person he was is also what’s happened to Gatsby, the book itself.”
• On Fitzgerald’s writing style
  • Not purple prose but "painterly," mannered, inventive. Each sentence is crafted, original, and surprising.
  • "He makes interesting language choices…it rips. I sat down thinking I would read the first 50 pages and I read almost the entire thing that afternoon.” – Rebecca [44:24]
• Comparison with Hemingway
  • Fitzgerald: Ornate, detailed, trying to capture the ineffable feeling of a moment.
  • Hemingway: Minimalist, suggestive.

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Notable Quotes & Literary Analysis

[46:25–59:05]

• Morality, ambiguity, and judgment
  • Jeff: "If a likable character is a thing that you need, I would run away." [75:11]
  • The novel offers no truly moral figures; characters’ flaws invite nuanced consideration.
  • "There are only the pursued, the pursuing, the busy and the tired." – Highlighted by Jeff [69:12]
  • On Tom: "One of those men who reached such an acute limited excellence at 21 that everything afterwards savors of anti climax." [52:16]
• Performance and Illusion
  • Gatsby’s carefully constructed persona—fake books, affected speech (“old sport”), houses as sets—mirrors the novel’s own mythos.
  • On the ‘uncut pages’ in Gatsby’s library: "…it’s the perfect representation of someone representing that they have a library." – Jeff [40:38]
• Social Critique
  • Tom Buchanan: Early example of the racist, blustering American oligarch—timelessly recognizable.
  • "Peaked in high school is a hundred years old." – Jeff [52:30]
  • The rich: "They were careless people, they smashed up things and creatures and then retreated back into their money…" [61:08]
• On Daisy:
  • "Daisy is in love with Gatsby…except that Daisy acknowledges that she’s also loved Tom…Gatsby needs her to say it’s always been you. And Daisy can’t say that." [24:19]
• Self-invention and the American Dream
  • Gatsby’s name isn’t even real—he invented his entire persona to fit a 17-year-old’s fantasy [71:21].
  • "He had thrown himself into it with creative passion…No amount of fire or freshness can challenge what a man will store up in his ghostly heart." – [71:06]
• Rebecca’s take:
  • "It’s a real kind of arrested development. But instead of saying like, he invented himself at 17 and he never grew, [Fitzgerald] gives us this beautiful…like he conceived of this thing and he stayed faith—like what a sentence." [71:58]

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Memorable Moments & Passages

[68:15–73:33]

• Standout lines:
  • "I was within and without, simultaneously enchanted and repelled by the inexhaustible variety of life." – [68:28]
  • "Reserving judgments is a matter of infinite hope." – [69:16]
  • On Gatsby’s smile: "It was one of those rare smiles with a quality of eternal reassurance in it…It understood you just as far as you wanted to be understood, believed in you as you would like to believe in yourself…" – Jeff’s favorite passage [72:05]
  • “In his blue gardens men and girls came and went like moths among the whisperings and the champagne of the stars.” [69:41]
• Satire in the title:
  • "The Great Gatsby" is deeply ironic—Fitzgerald is “satirical…there’s a satirical cutting element to this.” – Jeff [63:46]
• On adaptations:
  • "All of them unsatisfying." – Jeff [61:45] (Referencing every film version, from Redford to Luhrmann.)
• On reading as adults:
  • "Don’t trust your teenage reading of this. If the last time you touched this book was high school…tilt into yes, I think this one is worth jumping in." – Rebecca [78:28]

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Modern Resonance & Legacy

[55:49–79:51]

• Why Gatsby endures:
  • Its critique of wealth, performance, and longing remains immediately relevant ("hasn’t aged a day") [61:36].
  • Gatsby as urtext for “rich people behaving badly, never happy despite their means”—as in "Succession."
  • Archetypes (Gatsby, Carraway) recur in both literature and reality TV.
  • “The pleasure is, wow, these people are terrible. And watching that they can access everything except the one thing that really matters.” – Rebecca [55:29]
• On moral lessons:
  • Gatsby refuses to spell out easy lessons; it’s about questions, not “the lesson written across the last page.” [50:47]
  • Returning as adults allows for richer appreciation of ambiguity, artistry, and sadness.
• On remixes and further reading:
  • Numerous Gatsby-inspired works exist: “Beautiful Little Fools” (focus on the women), "The Great Man" (Black LA elite), "So We Read On" (Corrigan) [65:08–66:26].
  • Next steps: Dive into more Fitzgerald (e.g., "Tender Is the Night") or explore contemporary takes/remixes.

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Who Should Read Gatsby?

[75:06–77:14]

• Lovers of rich, complex sentences and subtle social observation.
• Readers interested in "morally gray areas."
• People who like “eavesdropping at dinner” on interpersonal drama. [75:43]
• Not for: Those seeking clear moral binaries or unambiguously likable protagonists.
• “The ask is not large”—at <200 pages, it rewards a return visit.

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Conclusion

[78:28–79:51]

• Gatsby’s archetypes and themes echo through literature and culture.
• The novel is not just a literary monument but a living, interpretable artifact—always worth a new look, especially as an adult.
• “There’s a reason we started with it…there is a lot to be found. There’s a lot to talk about. There’s a lot to wrestle with.” – Rebecca [78:28]

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Key Timestamps

• What the podcast is about: [04:13–11:37]
• Gatsby plot intro: [18:18]
• Major themes & critique: [21:37–29:06]
• Fitzgerald’s context & impact: [34:28–41:19]
• Reading Gatsby as adults: [43:39–46:25]
• Best lines, literary analysis: [68:15–75:06]
• Who is Gatsby for?: [75:11–77:14]
• Closing thoughts: [78:28–79:51]

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Notable Quotes

• "News flash: The Great Gatsby is fucking awesome." – Rebecca [44:24]
• "It was one of those rare smiles with a quality of eternal reassurance in it..." – Fitzgerald, read by Jeff [72:05]
• "They were careless people, they smashed up things and creatures and then retreated back into their money..." – Fitzgerald, referenced by Rebecca [61:08]
• "If you need a likable character, I would run away." – Jeff [75:11]
• "The book is literally and spiritually a car crash." – Rebecca [67:46]
• "Don’t trust your teenage reading of this…tilt into yes." – Rebecca [78:28]

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Zero to Well-Read delivers an essential, entertaining guide to Gatsby’s mystique—sharp enough for newbies, layered enough for the well-read—reminding listeners that the “green light” at the end of the dock is always worth chasing anew.

Transcript

[A]

This season of Zero to well Read is sponsored by Thriftbooks. And it's a good thing, too, because Thriftbooks is a place to go to save money on books. To find an interesting edition, you can get a new edition. We can also find 19 million books, games, movies, gifts of all kinds. But I'm here to talk about a few big picks for Great Gatsby editions to find. Probably the standard one. Right now it's called the Author's Edition from Simon and Schuster, and it has an introduction by the one, the only Jesmyn Ward. You can get that new for $14.43. As I sit here in the United States, there's a couple other things. There's so many other things you get, too. You can get a Penguin critical studies guide if you really want a deep dive. That's a paperback in very good condition for $6.59. There's a Harold Bloom version, part of his series of classics. You can get a graphic novel like new for 1299. There's a deluxe edition. I'm seeing right here, the paperback for $19.37. That's new. You could also set a wish list here. If you see one of these you like. But you know what? There's not one in the condition I want, or they're temporarily out of stock. Set your wish list and keep track of the ones you want. Please do not buy the 1974 DVD of the Great Gatsby starring Mia Farrow and Robert Redford. That's a tip from me to you, sponsored by Thriftbooks. Thanks for them sponsoring the show. Let's get back into it. Hey, everybody, quick word here. This is a rerun. We do this. We've done this twice. This is now our second time. Rebecca, we're representing our first episode of Zero to well Read, which we did in the fall. The Great Gatsby by F. Scott Fitzgerald. One is great to bring it back from the archive. People talk about Great Gatsby a lot. Still doing quite well, people listening and finding that episode. But also, Rebecca, we could use a break in between here. And I thought it was kind of a fun time to take stock of where we've come from, what we've done, what we've learned in this episode. We have left the preamble, what we're going to do with this show, our intentions behind it. I don't think any of that's changed. And frankly, we haven't changed much of the format already. I'm a little surprised. Rebecca, how about you?

[B]

Yeah, we've been pretty faithful to it. We've added one question to the immortal questions that all art asks. We incorporated free will, real or no. I think Oedipus gave us that one.

[A]

Maybe.

[B]

Maybe it came a little bit later. But we have been pretty faithful to the structure, which I both am surprised and not like. We like to dial in a thing before we start. And we did so much thinking and talking about what we wanted this show to be. If you've been listening for a while, you can probably just kind of fast forward through the first 10 minutes and then get right into Gatsby. But if you're newer to the show, it might be fun, I think, to hear us talk about, on the very first episode, what we were hoping to do here. And now that we're nine months in, we're cruising toward our first birthday. We've rolled past 600,000 downloads. It is nice to take stock and see, like, this has been the project so far that I hoped it would be. We've had a lot of fun, gotten to discover great books together, revisit great books together. And the best part has been hearing from listeners that this is helping them tackle books that either they've never read or that it's been a long time since they picked up.

[A]

Yeah. So if you're new and you haven't listened to this episode, here you go. If you've been listening for a while, how much have we changed on the Book Riot podcast? Things we did 15 years ago. 15 years ago sound quite different, but here we are. So this is the Great Gatsby by F. Goss Fitzgerald. You know, we could probably do a whole new episode, not just rerun it sometime in the future. Be fun to do a redux at some point.

[B]

Yeah, I think we'll revisit it and we'll be back next week with another brand new book for you.

[A]

All right, here we go. Welcome to Zero to well read a podcast about everything you need to know about the books you wish you'd read. I'm Jeff o'. Neill.

[B]

And I'm Rebecca Schinsky. Settle in, old sport. We're going to kick things off with the Great Gatsby by F. Scott Fitzgerald on the occasion this year of its 100th anniversary. But since we're all new here, this is our first time at Zero to well read. We're going to talk a little bit first about what we're doing with this podcast.

[A]

So Rebecca and I have been stewing on something in this vein for a long time. I'm mixing my metaphors here, though Fitzgerald does that quite a bit. So maybe I'm in the right, in the right zone of a show that engages deeply and entertainingly and sillily with a book, but also gives us some sense of the context. Right. So if you miss English class but also like podcast vibes, this is the show for you. The kind of show, frankly, we would like to listen to. I don't think is unfair to say

[B]

I think that's right. We're really aiming for the edutainment zone with good doses of both the Edu and the tainment. If you have found your way into this feed and you don't know who we are, Jeff is the it's been a while since we had a new podcast feed. Jeff is the CEO and one of the co founders of Book Riot. I am the chief of staff. We've been working together, writing about books on the Internet together since 2011, each of us individually, I think since about 2008. So we've got a lot of years behind us of writing and now talking about books on the Internet. We've been hosting the Book Riot podcast together for 11 or 12 years now. That's where we talk about news in the world of books and reading. But we've been, you know, talking to readers professionally now for more than a decade. And one of the things that we consistently hear is people, like, people want to be, well, read. They want to know about books, they want to know what's going on. They also want to know what the big deal is about the books that they feel like they're supposed to have read. Maybe you don't actually want to read the Great Gatsby, but you want to, like, have the gist or the talking points. It's been a while since high school, and we do know that a lot of readers carry around this fear that, like, oh God, I'm going to go to a cocktail party and somebody's going to ask my take on Dostoevsky. And that probably doesn't happen, but we're going to prepare you for it just in case and hopefully have a lot of fun along the way. So we have taken the Book Riot approach to what well read means, which is some classics, some of the canonical things, stuff that has been important in forming the culture. Some of it will still be relevant. Some will be. You should know about this anyway. And then also things that have been big contemporary or modern hits, some bestsellers. You might see some sparkly vampires later in the season here. I'm just gonna toss that out there. That is the book riot approach that to be well read means to have a sense of what is going on in the bookish zeitgeist and how we got here. So classics from along the way and more recent reads.

[A]

And I think too there's an enduring interest in art, of course, but I think for both of us, and I think I'm detecting it with what little Internet spidey sense, I have some increase in desire for some different kind of engagement with the world, with art, with things that go on that is beyond what the modern Internet is designed to do. I think we are not take merchants. This is not going to be coming in and be like, this book sucks, let's cancel all this. We're going to wrestle with the complexity, I think is fair to say our opinion or review of the book is not what you should be here. Nor is that what we want to do, what we like to do. And I think we've had the best time talking about books that we sort of didn't quote unquote, like or not. There's always something to talk about. And the book itself is a strata on which we can dance a little bit and have a good time and really engage with each other, with the listeners out there and with sort of the enduring questions of art and life and what these books bring to the table. And, you know, one of the things that's hard to remember about these books, we're doing the Great Gatsby today. I don't know if we said that is at the time, all of these works were contemporary.

[B]

Yes.

[A]

No book was written already 300 years old and moldering and sort of already having a position in the canon. And so I think we want to try to wrestle and deal and encounter that contemporariness. What was new, what was interesting, what and then what endures. And they'll of course talk about what falls away or what seems anachronistic or, you know, what might be the age, the worst here. And we've definitely got some candidates for the Great Gatsby. But I think every time I return to one of these books, I find myself saying, wow, that's weird that they did that. And oh my God, it's weird that they felt that way too.

[B]

Right. Yeah. There is some universal human experience that comes through and it's really nice to be reminded of that and grounded in it when you go back to older books. And also we take a real yes and approach to this. So it will be classics, because there are things that still endure and we're not saying read classics to or read serious literature to the detriment of having fun with your reading life as well. We're going to have hopefully a lot of fun here. We don't want to be all vegetables. Like this should be vegetables and dessert and a good hearty main entree, a main dish. I'm really sorry that I'm on culinary metaphors this morning.

[A]

Well, it is, it is so interesting because the food metaphor, especially reading has been around as long as I can remember, right. That there is part of your reading quote unquote diet that is vegetable and then I guess some that could be candy. Like we see these brain candy things like this. If we extend the cooking metaphor and we're going to have some sort of moratorium on it. But like all in vegetables can be really good if done correctly, done well. And I think one, you know, if we, if we maybe end the, the food metaphor here. A lot of these are amazing Brussels sprouts, right. That you would proactively order done correctly and done well and, and you know, brought to it a sense of adventure. When I was a kid, I hated brussels sprouts. But there's all the preparation, right.

[B]

And I think there's really some, something to be said for and some fun to be had in coming to maybe what felt like over boiled Brussels sprouts. When you were in high school and they were like forcing you to read these books that you're frankly too young to really relate to. Like at 17, none of us really have the life experience to connect deeply with most of these stories in the way that they're intended to be read. But that's the age we are when the education system has us as a captive audience. So they got to get it in somehow. It's really cool to go back as an adult within a whole set of life experiences and you know, a fully formed frontal cortex and be able to encounter a work. I think more as an author intended it to be encountered, but also read through modernize what still resonates, what doesn't resonate anymore because culture has changed so much. What are the through lines? And as you were saying, I think none of us are happy about how much time we spend scrolling. Everybody I talk to wants to spend less time looking at their phone. And a great way to do that is to pick up a book that's going to keep you deeply engaged. And often the ones that keep you deeply engaged are the ones that we most want to talk to somebody else about. And if your friends aren't Going to pick up the Great Gatsby to read with you. That's what we're here for, right?

[A]

And it's an occasion. And this is going to sound maybe churlish and old fashioned or scoldy, but like it gives me, I'll speak for myself. An occasion to think. And this is this, this is in short supply occasions to think. Because your phone and the algorithms that power your scrolling are not interested in gauging your thinking parts. They're interested in gauging sort of your pleasure reward system and rage machines and things like this. But the idea of taking a book like this seriously and going beyond the I liked it or I didn't or this was bad or this character sucked or oh my gosh, this was amazing plot twist, those things certainly happen. But there are also sentences in the Great Gatsby that I could do a full hour on by themselves, frankly.

[B]

Yeah. Yes. As we're recording this In July of 2025, MIT has just put out a study looking at how the use of AI impacts critical thinking.

[A]

That has got passed around my chat. I don't know, we haven't talked about that directly, but I figured you had seen it.

[B]

Yeah, we didn't talk about it on the Book Riot news show. I think it hit when you were on vacation. But that has gone to all the bookish corners. I think it's gone to many of the educational corners. Everybody who's concerned about what AI might be, not to like the quality of anything except but to our ability to write things ourselves, to think through things ourselves. And this was a small study and it was early, but it does seem that there is reason to believe that, and this makes just sort of intuitive sense that allowing a chatbot to write things for you would make you rusty. Your brain is, if you don't use it, you lose it. And when I sat down last week and spent an afternoon reading the Great Gatsby, my brain had feelings that it hadn't had in a while. And I would like to have more of that and less of all the other junk.

[A]

An excuse to pause for a moment on one of those sentences to underline and return it. We're not going to get to every sentence that we find interesting because that would be a 24 hour show. And maybe that's the thing. Like the Great Gatsby, sentence by sentence is an incredible YouTube series that I would probably watch.

[B]

We ever have to do like a

[A]

24 hour marathon fundraiser, like some sort of fundraiser. You know, Eric, one of our co conspirators here at Book Riot is doing a Reading as Resistance series. And that's political resistance. And I was thinking about that. I was walking around Washington D.C. in and out of the Library of Congress and the Folger Shakespeare Library, and I think I saw reading as resistance or resist. And that's I was thinking about in terms of this show, because I was thinking about this show and what we wanted to do about like, rather than political resistance. Another valence of that metaphor is like resistance training, like resistance bands. And reading as resistance to an intellectual sluggishness and intellectual shortcuts I think is a really interesting idea.

[B]

One of my friends, her favorite insult when she's talking about someone she has no respect for is he's not a very nuanced thinker. And I want to think about the work we're doing for this show as counter to that. How do we prevent ourselves from becoming people who are not very nuanced thinkers? And this is a time in our culture where the ability to actually engage with a source material and not just a headline, to ask questions about it, to think critically about it, impacts us not just personally, not just the erosion or protection of our intellectual skills from AI, but politically and socially. And we talk at Book Riot all the time about how reading is and has always been political. And I think insofar as zero to, well, read carries politics, it's that reading in this way is a piece of how we want to show up in the world, a piece of how we wish to engage with the world. And that reading books that challenge you and taking the time to let them challenge you is one way to develop those skills. We also say that reading is not resistance by itself. This is a tool that you use to help you as you show up in the world and try to shape it in the ways that align with your values.

[A]

All right, so let's talk a little bit about how this is going to work. So for each of these books, we'll of course have read the book, ready to talk about it. Our goal is that you do not need to have had read the book to enjoy get something out of what we do here. And if you have, you should also get something out of it. A very tricky situation we've set ourselves up for Rebecca, but we're going to see how we do it.

[B]

A little bit of a high wire act, but I think we can do it.

[A]

We'll do some background. This is not a lecture on this author or this book or sort of literary traditions, but I think both of us think that Some of that can be quite helpful. We'll talk about the book itself, the ins and outs, the parts that we found interesting, not just the plot, but what does it care about? What is it wrestling with? What's age like? The poor? What's aged? Well, I think we haven't really talked about this, but one idea is part of it is for people who haven't read this book and others. Is. Is this something that I might want to pick up?

[B]

Oh, absolutely.

[A]

So I think we'll talk towards the end, probably, what kinds of reader do we think would really like this and get something. And I even want to move beyond that metaphor, like find it psychologically rich to quote one of our favorite new phrases and then which kind of readers maybe move on to the next. Right. Or this isn't one that maybe you need necessarily to enter in because I don't think. Well, maybe with the exception of Shakespeare, I don't think there is any single author or text that has to go into your golf club bag to be well read. But I think maybe Shakespeare. But outside of that, like, there is no a hundred. But there is a hundred, if that makes sense.

[B]

Yeah. We want to give you a firm foundation. And I think in the course of doing this, we will each end up talking about books that we've read for this project that we don't particularly like, but we're trying to find value from. Like, stay tuned for when we eventually read Jane Austen, who I notoriously am not a fan of, but I can find something.

[A]

We're going to turn you around. You're going to have a great time with Jane Austen.

[B]

I want to have a deeper appreciation for. For why Jane Austen matters. And I think that's really what this show is about. Why is this book important? Why has it been important to people? What does it have to teach us? And that the entertainment part of reading the Did I like it? Is important, but secondary to what else is going on here. So, yeah, you don't have to have read all of the books, but hopefully even the ones that you think you're not interested in, you can learn something about. And then you really don't have to read it because we'll have given you talking points.

[A]

All right, with that, it's time to move on to post world 1America, the age of flappers and drinking gins and really dangerous automobile travel. That's one thing we learned from the Great Gatsby. Rebecca, Rebecca, I'm going to kick it over to you. What is the Great Gatsby about?

[B]

Okay, so there's what happens and there's what it's about.

[A]

Let's start with what happens, maybe.

[B]

Okay, so what happens is Nick Carraway is our narrator. He's in his late 20s. He's a dude from the Midwest. But he has longed to go to the big city, strike it rich, and

[A]

who among us, Right?

[B]

Exactly. So when we meet Nick Carraway, he has moved to the West Egg neighborhood, which is fictional of Long island, but think like Hamptony Hampton's vibes. He is living in a small house next door to a mansion owned by a man he comes to find out is named Jay Gatsby. Gatsby is mysterious and he's glamorous and he throws these huge parties. And because Caraway lives next door to him, he also gets to observe him just like standing alone in his yard, staring across the water at this green light coming from a house along the way. When the book begins, Caraway has been invited to lunch at the home of a friend, Daisy Buchanan, and her husband, Tom. They have a bad thing going. Tom is racist, he's abusive, he's having an affair. And everybody, including Daisy, knows it. Like, they're both miserable. It's obvious to Caraway as soon as lunch starts, this is not good. And as Nick gets to know Gatsby, he discovers that Gatsby and Daisy have known each other. That actually Gatsby bought this house because five years ago he met Daisy and fell for her. He knows that she lives across the way, and he's been looking for her, a way to reconnect with her. So the book is shaped by Gatsby's longing for the past, longing for the life that he wishes he could have had with her. And really that he's stuck on one vision of what his life should have been. He's built this whole edifice around trying to someday get the one that got away. And it's about wealth and excess and the American dream and who gets access to it and who doesn't. And the cost of constructing a life around other people's perceptions and your desire to satisfy those. What else?

[A]

Yeah, so, I mean, the plot is. It's again, less than 200 pages. And it came at a time in Fitzgerald's life in which he had had a huge success with his first novel that is about the Princeton life and then had a bit of a downturn. And he worked on Gatsby, and he and his editor, Maxwell Perkins, had a lot of hopes for it. His own personal life is suffused throughout his own writing. You know, he. This idea of not having enough money yet to woo the one you want is very much he and Zelda a tempestuous back and forth complicated, bad romance. Right? In kind of a Lady Gaga sense, where it's like, it is attraction, but also maybe unhealthy, but also there's nothing we can do about it. So we're gonna ride this thing off the cliff and into the fiery maw below. And the time period itself, the Roaring twenties. I think one of the reasons we wanted to start with Gatsby, a, it's a hundred years anniversary since it was written. So that's a big, nice number for Internet content makers to make stuff around. But at the same time, it represents, I think, you know, it is one of the few candidates that someone could credibly say, this is the great American novel. I don't believe that thing exists. But, like, this is one of the candidates you might reach for and people do reach for.

[B]

And it is like, it's messy as hell.

[A]

I was just talking about this for beach reads. It is a messy summer vibes novel.

[B]

It is. The whole thing happens over the summer once Gatsby and Nick figure out that they have Daisy in common. Gatsby talks Nick into hosting tea at his house, inviting Daisy, telling Daisy not to bring her husband, Tom, so that Gatsby can be like, hey, guess what? Here I am. I've been pining for you for five years. And then Nick just, like, puts his hands in his pockets and walks out of the room whistling. Like, what you guys do in here is up to you. Yeah.

[A]

And they all do things like that, set each other up and have these really awkward social engagements and permutations. I'd be like, I would run. That's how I know Caraway is not really a Midwesterner. He would never. That's a joke.

[B]

100%. Like, caraway goes into the city one day with Tom. They stop along the way to pick up the woman who turns out as Tom's mistress and go to, like, the love nest that Tom keeps with Myrtle. Along the way, she stops and buys a puppy for, like, unknown reasons. They have, like, before they have a knockdown, drag out, literally. But before they have that, Caraway, like, goes away from the apartment to pick something up, comes back, and Tom and Myrtle are just in the bedroom. It's like, the most awkward thing ever. Your friend brought you along while he's having an affair. Like, I kept thinking, like, Real Housewives of West Egg.

[A]

Listen, I have this one for you. I've been saving it I'll use it here. Alternate title. Crazy Rich Caucasians. It really is.

[B]

It really. It really.

[A]

It really is.

[B]

Yeah, it really is. So Daisy and Gatsby reconnect now they're having an affair. Caraway knows all about this. It runs over the course of the summer. And then like in the middle of an August heat wave, they all end up in a hotel room in the city together. Which drunk.

[A]

Which is always helpful for these kinds of encounters. 100 degree, no air conditioning. Remember it's 19, 19, 20 something.

[B]

25, 28 ye, 24, 25. Something like that. And. And then it comes out that Daisy is in love with Gatsby. You would think that Gatsby would be happy about this revelation, except that Daisy acknowledges that she's also loved Tom. And there's like real. I kept thinking about that line from Barbie where Ken sings about blonde fragility. Like that he's. That Gatsby loses his shit because he's like, oh, you loved him too. Like it's not sufficient that Daisy is in the moment.

[A]

It's the real climax of the book, right? This moment where Daisy admits she has loved them both, right? That it's not one or the other, which we can talk about that. But that is the climax. Everything else sort of sees.

[B]

You would think that this is the thing Gatsby has been wanting is for Daisy to say, I'm in love with him. I'm leaving you, Tom. Like we've been having an affair and that's not enough. Gatsby needs her to say it's always been you. And Daisy can't say that. Right? She has not spent five years standing on the dock, staring at the light across the way, pining for him. She has built this life that much as she might regret it, like is her life. And she has loved Tom and she is staying in that relationship for reasons that we can't really know but like that's when the whole thing comes to a head. And then they. Everybody again. It's August and it's hot and everybody is drunk and it's like the middle of the day and they get in their cars to head back to west

[A]

and they don't have anti like brakes. They don't have. I mean we're running in death traps. These things are bombs flying down the highway with gin soaked, emotionally distraught people. Like I have read about the history of highway safety. Let's just say the 1920s is not the time you wanted to be flying back and forth from Long island in New York City on the Highway. There were no highways. There were just roads.

[B]

In one of the great coincidences of fiction, which you get to do if you can pull it off the way F. Scott Fitzgerald pulls it off, Myrtle, Tom's mistress, happens to be running out of her home because her husband has found out she's cheating and he's tried to like basically lock her in the attic to keep her from leaving.

[A]

Things are going great with the Wilsons.

[B]

And just as she running out, Gatsby and Daisy in his car. And it's never clarified which of them was driving, come around the curve and they hit Myrtle and she dies. And they take off like it's truly a hit and run. The car gets parked at Gatsby's house to try to hide it. Tom knows what's happened now. Tom knows that his wife has been cheating on him. He's abusive and terrible. What's going to happen to Daisy, we don't know. And Myrtle Wilson's husband comes for Gatsby and shoots him. And eventually Gatsby dies alone. And none of his friends who have come to his fancy parties show up for his funeral. Just his father from the Midwest who found out about it in the paper.

[A]

Not even his mafia handler comes and shows up at his funeral there. So at the time, Fitzgerald is one of those people. A lot of the authors we're going to talk about in this series have achieved this iconic status which actually blinds culture from seeing them directly. They become a totem of themselves and the Gatsby. We talked about this in the run up of the show. The thing that's most enduring about Gatsby for most people is the idea of a Gatsby themed party. Baz Luhrmann probably only makes that adaptation because this idea of the Gatsby theme party is out there, of the music and the ambiance and the clothes and the long cigarette holder and this sort of ironical pose. You know, we get this from Jordan Baker. It's like baked into this. And that's one of the things that struck me. I haven't read this book for. We can get to our own reactions in relationship to it. But that's one of the things that struck me is that there's a self awareness built into it already that they're playing parts which I had forgotten or didn't pick up the first time and that those poses then get stripped away. And once they get stripped away, they're raw, they're exposed, and they have really no capacity to deal with what's left over when those things are stripped away.

[B]

That was also astonishing that Fitzgerald is 29 when this book comes out. Carraway is 29 in the book. His 30th birthday is approaching and there is a remarkable self awareness and a surprising amount of insight into their lives. What to be disillusioned about? Carraway's perspective on Gatsby and the hollowness of that. Like he has this huge home but it's always empty. He throws these parties but like they're parties that there's a great line like no one was invited to them. People just simply came. People just show up to his house because they're not interested in him. They just all want to be at the party.

[A]

And he has at the scene. Yeah.

[B]

And he's the, he's a tool for that. But there's no real connection for him. And this is a man who has like spent the last five years pining after someone that he knew very briefly but convinced himself was the girl of his dreams and that if he could construct this life where he looked wealthy, he would get her. So it's just a huge house of cards built on a lot of assumptions that Gatsby has made and Carraway can see that and tells us like from the very first couple of pages that he. Well, first Carraway tells us that he doesn't judge anybody and then he tells us that he had scorn for everything that Gatsby stood for from the start. But this is like a remarkably mature perspective for someone to have written in their mid-20s. And I had a lot of thoughts about like the mid-20s ain't what they used to be.

[C]

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[A]

Well, I mean, I've said before that like to be 29 is the most dangerous age because you feel like you know something and you still sort of don't on the whole. Yeah, I think one so Caraway's observation. And this is maybe to my mind, I'm not going to speak for everyone who's ever read Fitzgerald. That'd be too much. Rebecca. I think to try to do to my mind one of, if not Fitzgerald's greatest skills or projects is to try to describe the ineffable something of someone. Right. In talking of Gatsby's smile. That's one of my passages. We'll go for a minute. Or Daisy's voice or the dynamics between someone or Jordan Baker's repose on the couch. He uses these unusual descriptors and he very much cares about capturing the aura, the effect that someone has or that some moment like the plot of Gatsby is lewd. It's salacious, but for me, sort of beside the point, frankly, because the moments that matter is describing Gatsby after this thing happens and how he seems right or how this party felt or how this conversation went. That seems to me the pleasure. Those are the beachheads of which I want to. That's a beach I want to luxuriate on.

[B]

It is a really singular kind of observation of both people and society, group functions. And maybe it's the kind of thing that you have to come from somewhere like the Midwest into a place like that.

[A]

I think that outsideerness, you know, you have to be from somewhere else to see that this is the water.

[B]

Right. Like Gatsby. Fitzgerald was born to a middle class family in the Midwest. He aspired to east coast wealth, to glamour. He dropped out of Princeton in 1917 and he joined the army. And while he was stationed in Alabama, he melt. He met Zelda Sayre, who would become his wife. But she initially rejected his proposals because he didn't have any money.

[A]

Yeah, it's in there. I mean it's just. That's not even subtext.

[B]

It's just text like. So this is where Gatsby gets the idea that he needs to look like he needs. He's rich. And how Gatsby comes into his money and the ways that he is willing to be morally compromised in order to build up all of this wealth to try to get this girl who doesn't even know that he's still after her, except for a wild coincidence of a guy moves in next door. Like it's just that outsider perspective, I think really, really matters here. And that then Zelda agrees to marry Fitzgerald. He becomes successful and that doesn't solve all of the problems. He's an alcoholic. Zelda has really serious Mental health difficulties, and they both die pretty young. Fitzgerald dies in 1944, and at that time, he thinks that the book is a failure.

[A]

Yeah, I mean, it is amazing. And this is something we're going to see over time, especially for older books. The life these books have had since is sort of completely removed from what the author or the time period had. And as you mentioned, you have in the notes, you're like, this book became famous later, after Fitzgerald's death. There was this really important edition of, I think, the Last Tycoon that Edmund White, who Fitzgerald met at Princeton, put out that included all of the Great Gatsby in it. And so this Fitzgerald as a tragic figure and chronicler of tragic figures himself, I think was very interesting to people. And then Gatsby gets picked up. It becomes a paperback edition distributed through World War II. Hundreds and 150,000. And then becomes. And we'll put a link in the show notes, we have some other reading here. Becomes a staple of high school reading for reasons that I think are both interesting and sort of beyond the scope here. But it is short. Right. It does have this salacious plot that you can talk about. And the thing that got me this time is how obvious the obvious metaphors are, like the green light and Eckleberg and Perkins and Fitzgerald. Perkins writes to Fitzgerald and says, like, you've got this great metaphor. They're talking about the metaphor in it.

[B]

Yeah.

[A]

And, like, it's just on the page. It's so weird.

[B]

I remember, like, I will know the eyes of Dr. T.J. eckleberg, like, for the rest of my life because of how much my high school English teacher talked about it. And that was a surprising thing, going back and reading it, being like, oh, they only really mention it, like, three or four times. That it's.

[A]

But a metaphor that's mentioned three times is kind of weird for a book.

[B]

That it is that poetry potent and that present in it. Like, the book's initial reception was really interesting, like, well received by critics. It's Fitzgerald's third book, but not as well received as the first two. And it didn't sell nearly as well, I guess you were saying this. It only sold 25,000 copies in the first 15 years of its publication. And at that point in 1940, Fitzgerald writes to Zelda and says, my God, I am a forgotten man.

[A]

A little dramatic, maybe, but, I mean,

[B]

I think he probably tended to the dramatic. Gin soaked. Yeah, Gin soaked and emotional is a real vibe. And he's. He's. But he's been like, A darling of the literary scene. He's traveling back and forth to Europe. He's friends with Hemingway. But the Great Depression hits after the stock market fall in 1929, and the books fall out of favor. And, like, the discourse around this is interesting. Like, did they fall out of favor because culture was shifting and perspectives on wealth were shifting? Or like my reading of it is, most books fall out of favor.

[A]

Yeah. Your base case is that falls out of favor.

[B]

Right. But Fitzgerald dies believing that the book is a failure. And then in 1945, the Council on Books in Wartime picks a bunch of titles, as you were saying, to make cheap paperbacks out of. They send them to 150,000 members of the military overseas. Those guys read these books and they come back talking about them, and it brings back Great Gatsby into cultural awareness and Gatsby sticks. Then just 10 years later, Scribner published the first student edition in 1957. And Great Gatsby has been Scribner's bestselling book of the year basically every year since then.

[A]

Yeah, it's incredible. It really made Scribner and then Scribner, which became part of Simon and Schuster. It was one of the backlist workhorses that's really supported over time and these things. Then once they get sort of escape velocity in the culture and then there's really no going back. They have an inertia on its own. You couldn't really stop the Great Gatsby. Now it's a brand as much as actual book. And I guess as we go, maybe we'll transition here to our own initial reading experiences. What it was like to return to it is that's certainly how I remember encountering the Great Gatsby the first time I read it on my own. I was not assigned in high school. They wrote it in high school.

[B]

Oh, wow. Okay.

[A]

Is that I was sort of tackling one of them. Them. Right. Here's one of the ones you need to have gotten. And I will admit this, I don't remember my initial reaction other than I really was like, wow. But other than that, I've got no sense memory. Like, I think I even got a couple of the plot points wrong. But there's still a lot there. And I. The thing that really strikes me now is how Gatsby's portrayal of the kind of person he was is also what's happened to Gatsby, the book itself. Because the stuff, the cliches that have come out of it, like the old sport thing, was a put on and acknowledged as A put on in the book. Like Tom calls him out. Where did you get that?

[B]

What are we doing here?

[A]

What is that? He is playing someone who he thinks would do something like this. And he has this fake library. There's this really wild scene, it's very small, in which Nick Carraway is coming into Gatsby's house for the first time, which he's kitted out to essentially woo Daisy. This is like one of those birds that builds an elaborate nest. This is what he's done.

[B]

Someday she'll come over and someday she's gonna come. It's gonna make her love me and it's gonna.

[A]

And so there's this bespectacled old guy sitting in the library being like he's. He really did it. This is perfect. But what's perfect about it is that it's the perfect representation of someone representing that they have a library. But they've left the pages uncut on purpose because to cut them would be too far. But you have the books, but you actually do the thing. That's enough. And I know that you know that we know that I know that this is all a performance and that Gatsby's now cosplay is so mind blowingly perfect or terrible that it's kind of hard for me to get my head around.

[B]

Well, I think that's it. That it's so good. That's what's depressing about it, that he has built such a successfully fake life for himself. And if you're wondering what uncut pages are friends like.

[A]

Oh, sorry.

[B]

You know, if you've seen deckled edges on a book that is now like imitation of the way that books used to be printed, where the pages were still kind of bound on the edge and you would have to cut them apart to be able to flip the page and read. So deckling used to be incidental, not

[A]

like, not decorative symptom, not the cause.

[B]

Right. Yeah. I think that I definitely did not grasp how sad this book is and how depressing Gatsby's life is. When I was in high school, I think we read this my sophomore year. I remember a couple of the lines. I remember that Daisy's voice was full of money. I remember the thing about beautiful little fools. I remember the eyes of Dr. T.J.

[A]

eckelberg, the green light at the end of the doc. I mean some of that stuff I wrote, the actual reading experience.

[B]

Absolutely. Wrote an essay about. About what the symbolism of the green light at the end of the dock was.

[A]

That's what we have LLMs for now.

[B]

Right?

[A]

I mean, honestly, like, okay.

[B]

And I remember that, that Fitzgerald, in my, you know, whatever high school honors English was taught in contrast to Hemingway. Like, I also remember an assignment to write a short story in the style of either Fitzgerald or Hemingway. And that, you know, one would be like very straightforward language and short sentences and the other would be Fitzgerald. And. And I think that in the, what, like almost 30 years since then, my reading of Fitzgerald, I would have gone back to Fitzgerald sooner if I hadn't constructed this high school based memory of it as like, really flowery. As you were saying. The sentence structure is like original and it's surprising and really different from reading a book that is published or set today. He makes interesting language choices. I don't know how it felt to read it in 1925. I think some of the slang would have felt timely and it feels old and a mark of its time now. But this was. I don't remember having a great time when I read Gatsby in high school. It was a book I had to read for school and I was a nerd. So I wanted to understand why it was important. Important.

[A]

But you wanted the gold star for having read yet.

[B]

100% I wanted to be able to show up at the cocktail party and explain the meaning of the green light, you know, like, I can do that. We're good. No one has ever asked me to, very sadly. But sitting down to read it as an adult, like, first of all, I was like, hell yes. This book is 200 pages long. Like, thank the maker, sign me up. But also, like, it rips. I sat down thinking I would read the first 50 pages. And I read almost the entire thing that afternoon. And my husband came home from work and was like, how was your day? And I was like, news flash. The great Gatsby is fucking awesome.

[A]

Yeah. And that flower, I mean, I think the flowering. I hesitate to. Well, here. Can we reclaim flowery? Let's reclaim flowers are great. I love flowers again. And looking at a whole bunch of art museums, like, the idea of capturing the specificity and ornateness of kinds of flowers is really cool. And it's not purple prose, though. I think that's what it is. Like, he's using unusual. Like I had to quote, unquote, stop and consider what is going on with this? What is this description? What is going on with. There are words I don't remember ever knowing before. Pasquinade, dilatory. I'd like, look a couple things up and remember. And I don't know if at the time, I don't know if that was intended, but it makes you slow down. And he's really trying, with all of the sort of painterly tools that he has, to really capture the specificity of what he's feeling, to give a sense impression of what's going on. Whereas Hemingway, like, in the great example, Hills Light, he's doing as little as he can to give you that. Like, to give you, like. Can I just, like, sort of huff in that direction and you feel the whole thunderstorm. Whereas Fitzgerald's, like, painting every single wave and he's, like, trying to do something. It's very mannered, I guess, is maybe a way of putting it.

[B]

I think it's.

[A]

I find it very rich and stimulating.

[B]

Me, too. I found it to be a really literary method of world building. Like, this is what I want world building to be. Give me three sharp sentences that tell me exactly what it felt like to be in that place. I don't need, like, the 20 page history of where the marble from the house came from, or 45 more pages about the complex or how the money works and how much. Everything.

[A]

I was gonna say the complicated system

[B]

of government or any of those things. Like, I think that has its own utility in a different kind of book. But this is what I want from a literary writer is like, say the thing and say it beautifully and in a way that resonates, even if I do have to go look up a word. You know, like just. You feel like. You know what it would be like

[A]

to walk through sort of experiential articulation.

[B]

Right.

[A]

Yeah, I got the. I get that.

[B]

Yeah. You.

[A]

I can feel that.

[B]

You feel like if you. If you were to just be dropping into that party, you would know that this is a Gatsby party. Or like, oh, shit, I'm in that hotel room with them on this August afternoon. Like, you can feel all the bad decisions coming.

[A]

Yeah. You know, the rootlessness, the aimlessness. Right. Of the people who've already sort of made it to the mountaintop and then are sort of looking around and what's left is like, I guess I have to have the girl and have her completely. And that's the only thing never make anyone happy either. But, yeah, on second blush, I was surprised that to find myself really, to be more enamored with a sentence or a scene or a paragraph than the tragic comic character of Gatsby, which I think still hits. Right. I think this one of the. It's not just about the past, but I think the question of Judgment is very much there of, like, how do you think about flawed people? I felt that to be very contemporary, frankly. Like, you know, I don't want to. I don't. I don't want to talk about cancel culture at all. But what I do want to think about a little bit is how Caraway sort of vacillates his viewpoint on the people that he's encountering because there's no good character.

[B]

Oh, no.

[A]

And even, like, the monster is Tom Buchanan what Tom Buchanan represents, I think, pretty clearly. But even Tom Caraway says, I kind of get why he did it that way at one point. He doesn't like Tom. He doesn't want to be around tomorrow. But he doesn't eject Tom from his field of interest. He doesn't not ever consider Tom. He doesn't sort of make a final judgment on Tom, which I think the last line is much more famous than the first line in the great Scatsby. But this weird articulation of, you know, one thing I turn over in my mind again, I don't have exactly, maybe I'll get here in a second, is like my father said, not to judge people until you know where they came from. So this interplay of the past and the present and how much someone is accountable for their own actions, but how some of it can be attributed to where they came from. And both things are true, and they're in conflict and tension is wildly helpful as an adult, as a. Wildly helpful as a person in the world. And Caraway wrestling with that and saying, but for some people, I do, at some point, there are some actions you have to be like, that was a bad job, but does that mean they're a bad person? Does that mean they have to be exercised or ostracized? Maybe not. I don't know.

[B]

Yeah. And that, I think, also serves a couple functions for us as we're supposed to read or be challenged by Carraway because he's complicit in all. He's going along with all of it. He's the one who arranges for Daisy and Gatsby to get together. So he's facilitating these people having an affair. But we know that Daisy's husband is terrible, and we know that Nick can see what Gatsby is longing for. So maybe this is immoral, but how bad is it actually? And I think he's asking himself that question, what does it mean to see that, like, that Gatsby's life is pretty fake and pretty hollow to recognize that Gatsby's involved in some shady financial dealings, and Carraway holds himself out of those. But he certainly benefits from what Gatsby has done, and he gets access to that world and access to the glamour and access to dating a woman like Jordan Baker, even though he knows it's going to nowhere. And so he's, I think, both letting himself off the hook for some of this, like judging everybody more than he's willing to judge himself, but also inviting us into considering the ways that it's more complicated. There's not a straightforward reading, really, on any of these characters. And for a book that's 200 pages, that's great. First of all, like, it's. Everything is very compact. It packs a powerful punch. And that's a thing that I want more from fiction. One of the things we've talked about on the Book Riot podcast in the last year really, is seeing this uptick in even contemporary literary writers saying the thing, giving us the lesson, giving us the moral overtly. And I want fiction especially to function in a place that invites the questions, not where the lesson is just written across the last page. And Fitzgerald, I think, I think, sets the table for that really beautifully.

[A]

When we, I mean, there's. There's parts of it that still feel very contemporary. Because when you encounter and you go back to these works that again, you've read 30 years ago, that were written now, a hundred years ago, how much does our contemporary sensibility, our contemporary truths or understanding, do we bump against things that are representations here, worldviews, isms of various different kinds? This is not without. I mean, I think probably Meyer Wolfshum is probably this Jewish criminal figure, right? Though he has its own complication, right? Like, I tried to make it clear to someone, I'm their friend, whether alive rather than dead, not showing up at the funeral. But the moment that really struck me is like, this holds up better than I thought is our introduction to Tom Buchanan. And Tom Buchanan, who is described as having a cruel body, like his evening sort of hulking mass, and how he's put together and how he presents himself to the world. He enters into the room talking about this book. He just read about how the white race is going to be taken over and we got to do something about this. And then Daisy, sort of as an aside, Tom's gotten very serious. She takes air out of it right away. And the book doesn't come out and say, this is a bad and wrong idea. It's that, like, he sees a buffoon right away. And this is sort of a ridiculous position to hold from the first scene

[B]

with him, you know that if we ported him into 2025, like we know exactly which websites and cable news networks Tom would be reading.

[A]

Yeah.

[B]

One of my favorite lines in the book, one of my favorite descriptions was Caraway describing Tom as one of those men who reached such an acute limited excellence at 21 that everything afterwards savors of anti climax. Like, bro, peaked in high school.

[A]

Peaked in high school is a hundred years old. Like Fitz, it was Fitzgerald, the first person to do a peaked in high school. Like, again, it's peaked at Princeton or wherever Tom ended up going. But he's not a figure. And this is something that feels very Okoran to me. I would say that these clownish buffoon, buffoonish figures that seem to be the first inclination is to create them as objects in ridicule can still backhand you and break your nose, as he does later on. Like, these are. The buffoonishness is terrible. It's King Kong with the clown waist. Because they can still wreck your life, wreck the city and wreck the world. And that's where Buchanan is. And his desire, his desire of ownership is a twin of Gatsby's desire for ownership. Like, compared to Buchanan, Gatsby's a romantic. Like a flawed kind of romantic. And even romanticism itself, I think is one of the object of Fitzgerald's ire. Because this idea that there's this one person for you and they're soul mates and love forever and they can't have loved everyone else and everything has to be perfect. Perfect. That view is very much positioned as a engine of destruction. That one worldview, that one story, that one way of being and should it get adulterated, contaminated, otherwise compromised, we've got to drive the world into the fire is like in the book, that's not the way to be. That's going to lead to tears and death, frankly. And I found that to be pretty shocking to encounter here again.

[B]

Yeah, Jesmyn Ward wrote the introduction in the paperback copy. Fascinating that I have because I had to buy a new one. I couldn't find my high school one. And she makes a note there about like, what it's like to teach this to high schoolers and what young people see in it. But also how much of the subtext becomes clearer with age. And that it's for Gatsby, it's the love for that moment, like being the time that he knew Daisy has rendered all other avenues of possibility impossible to him. And that it's this, this fixation on one way that you think life has to be in order for you to be happy. And trying to drive exclusively towards building that one thing, everything else be damned. That is the thing that is most guaranteed to make you unhappy. And it'll destroy you and it'll destroy everybody in your orbit.

[A]

Yeah. And interestingly, I think one of the things that some of the theories about why it fell off during the Depression was that it was this, this representation of wealth. Right. It's hard to. I mean, I think that's one of the neat tricks Fitchel also pulls off is that you kind of want to spend time in the rooms, right. And in these moments, but you don't want to be these people and you don't really want to be around these people. And as it became almost a cliche of itself, it's like it's not a. I mean it is. Money is certainly part of it, there's no question about that. But it is also about things that transcend that these people are rich, that they put. They're in these certain situations. They have the ability to. They can do everything but the last thing they can buy. Everything but the thing they can't buy.

[B]

You know, very similar, I think to Succession, that a lot of the pleasure is, wow, these people are terrible. And watching that they can access everything except the one thing that really matters. Like this is a kind of tale as old as time. It's a trope that artists have been visiting and revisiting and probably will be

[A]

if we had sort of a. How does it hold up in terms of a modern sensibility skill? Well, remarkably well, I would say. It's, you know, it's certainly not going to map neatly onto everything that sort of a, sort of a left leaning literary person as we are are going to bump up against. And certainly if you have any kind of grace for 100 years ago, things were different. I think you're not going to find too much to sort of depress you or give you the yucks about it here. I did think it's funny you have in the trivia here that Caraway doesn't come out and say he hates phonies, but he's on phony watch. And that is very Holden Caufield coded, I would say at this point. And it's mentioned in Catcher in the Rye that it was a favorite of his mentioning Gatsby to someone, Someone like Salinger, like already. He was a person who would have maybe read this, a paperback in the army. Right. But I can see how this would have been very influential in Creating a Holden Caulfield like character because it is kind of, frankly, it's more of a coming of age story of Caraway of, like, trying to learn about the world and how to be a little bit later in life that Caulfield is representing in Caraway.

[B]

Yeah, most of the things that Caraway observes these people do. Like, this is a cautionary tale about how not to live. Which is the whole point that it looked that Gatsby's life looks like the life that people, many people think that they want. It's glamorous. There's all this money and the fancy parties and everybody wants to be around him and the whole nine. But he is lonely and miserable and fixated on the past in a way that he's never going to get over. And even when he gets the shot at the girl that got away, he can't be happy with it. Like, there is actually no making this man happy, which is its own kind of ruin. But then he makes such bad decisions that he ends up, you know, like, his life is actually ended by his involvement with all of these people. Interesting for how, like, how spicy Caraway's take really is on everything. That there aren't a lot of major controversies around it, like how terrible rich people can be is, I think, a permanently relevant stance to take this.

[A]

Rebecca. I think. I think that's an interesting point. And I think part of the reason this goes back to something we just said is there is not a neat quote you can pull and sort of meme to death about, like, money is the opiate of the mass. Like, I'm bastardizing, you know, Marxist. You mean the careless people thing you have, like, there's a couple of them, like, but it's so more nuanced than that that the critique is, is it's much more withering because of it. But it doesn't neatly come into, like, yeah, it's not the jungle, but for rich people, like, it's not an Upton Clinton Clark expose because Caraway is adjacent to it and he's a Bonds tradesperson. It's not like he's a brickworker or something that's observing all of this. But I think because the perspective is so articulate and sophisticated, it's not easy to essentialize and extract for future deployment and weaponization.

[B]

And he's so good at showing that he doesn't have to tell.

[A]

Yes. And I think that's what Fitzgerald is sort of most. And this is true in this side of paradise and the Beautiful, the Damned. He's sort of interested in the crackling air between two people who have a complicated relationship. Like that is his 1.21 gigawatts. Ride the lightning, Mr. Fusion. That's where he wants to be. He is so interested in those unspoken enacted dynamics, in trying to capture the feel of it, the experience of being in those rooms, that in doing that, I think he kind of maybe comes at a critique sideways, if there's such a critique, because money is corrupting and these people are kind of bad to each other and they're not interested in being good, I think is another thing that I noticed in being. They're not interested in anything. It's all an ironic pose and positionality.

[B]

Yeah, it's that they're not interested in anything, that there's nothing here. It's all edifice.

[A]

They're looking for the next party. And again, if you're putting this in a larger context of World War I, right, this great disillusionment. And what does it all mean? I think one thing that might strike a modern reader too is that if you have a character now that was set in, even if someone today was writing this story and Nick Carraway and all these dudes had been on the front lines in World War I, someone would have PTSD. It's kind of just mentioned like, oh, yeah, we were at the forest, right? I was at the battle line. I was the captain of the machine gun crew. And we don't talk about the war anymore, how casual it sort of was. But then you see the second order effects of like, all these people are looking for meaning after this great apocalypse and no one goes to church anymore, which they talk about. No one's showing up. They don't seem to be interested in philosophy or art or anything else like that. They don't even come. They know enough to buy the library to show the thing, but no one's going to read a book except for Caraway, right, who says, I'm going to study and I'm trying to do some other thing there. And that carelessness, right? So this is one of the great polls you have here. Tell me about the most modern reference to carelessness.

[B]

So, Sara Wynne Williams, who wrote the big Facebook expose earlier this year, the book was called Careless People, and it comes from a quote from Great Gatsby where Caraway is describing Tom and Daisy and the whole whole, really, the whole ilk. They were careless people. They smashed up things and creatures and then retreated back into their money or their vast carelessness or whatever it was that kept them together. And let other people clean up the mess they had made.

[A]

It hasn't aged a day. No, hasn't aged a day. On the adaptation fronts, I would say I'm not going to spend much time on this. All of them unsatisfied.

[B]

They all have terrible tomato ratings. Ratings. Like, when I finished the book last week, I thought, maybe I'll go back. I've never seen the 1974 adaptation with Robert Redford and Mia Farrow. And then I looked at everything and I was like, no, we're not going to spend two and a half hours that way. There's an adaptation from 2000 that I don't think I'd ever heard of with Toby Stevens.

[A]

I've been. I'd heard of it. I haven't seen it.

[B]

Who is Toby Stevens? I don't know. Mira Sorvino as Daisy and Paul Rudd as Nick Carraway. All right, I've seen the Baz Luhrmann one. I thought that was unsatisfying in its own ways. It's like this has been adapted. And there are a couple others. There are at least two other adaptations of it. None of them seem to have been well received. For what Fitzgerald was able to capture so well on the page, it doesn't seem that anybody has had much success adapting it to the screen.

[A]

Yeah. So if you wondered, F. Scott Fitzgerald and Francis Scott Key. Yeah, they are related. Fitzgerald was named after Francis Scott Key, of course. Wrote the National Anthem. I didn't know you got rejected titles here. Let's just say they landed on the right one.

[B]

F. Scott Fitzgerald. Shitty at titling books.

[A]

Like, you don't think the gold hatted Gatsby would have been better?

[B]

Among the ash heaps and millionaires, a

[A]

high bouncing lover really is an avoided

[B]

mistake on the road to West Egg. Like, okay, simply Gatsby. Sure. My favorite of the rejected ones is Trimalchio in West Egg. And I had to Google, like, what the fuck is a Trimalchio? It's. Trimalchio was a character in Satyricon by Petronius, who was known for his lavish displays of wealth. So, like, good call on not putting an already obscure character's name into a book title like this. We would not be sitting here in 2020.

[A]

In 2025 was like saying Romeo. I mean, I had to look it up again. I recognized. I was like, I think that's a literary character. But that was a real bad one too. I mean, the Great Gatsby. This is one of my hot takes here is.

[B]

I love this.

[A]

It's ironic. The title is ironic, and this goes back to the point I was making before. But Fitzgerald's satirical. I mean, there's a satire element to this. It's not a farce, but there's a satirical cutting element to this. And this greatness is sort of. I think if greatness could be in quotes, maybe that's a better description of it.

[B]

One of the pieces I read researching the show today refer to it like. Think about it as a magician. The Great Gatsby.

[A]

Gatsby the Great maybe captures the. Weirdly just moving the definite article around, I think captures a little bit more. That's a really good point. But it's built into the title of Caraway is evaluating this greatness. And it's not great. And yet it is. Because he did this thing.

[B]

He's really successfully created the illusion.

[A]

The illusion. But like a magician, the illusion is amazing in itself, right? That he pulled off this neat trick of finding himself at Oxford and then leveraging that into something else and becoming the great party master of Long island in the Roaring Twenties to the point where he became a legendary and mythic figure by creation and accident at the same time. Pretty amazing at this point.

[B]

Rita likes this feels so singular to me that I really struggled with. Where do you go?

[A]

I don't have a good one. Really don't.

[B]

If you like Gatsby, I think you do. Go back to more Fitzgerald. Tender Is the Night this side of Paradise. It's been a while since I read those, but I think I remember liking Tender Is the Night better.

[A]

I. I like them. And Beautiful in the Day. I like them all.

[B]

And those are great book titles. Also like what happened to him when he got to the Greek.

[A]

Those are all pulled from Shakespeare, so I'm pretty sure Hemingway did it too. They both were pulling for Shakespeare. For Whom the Bell Tolls, Farewell the Arms. Those are amazing. You know why? Because the Bard wrote them.

[B]

And see above. Read. You don't have to read anything. Except maybe you do have to read Shakespeare.

[A]

Yeah, I went looking.

[B]

So when Gatsby started coming into Public Domain, there were a ton of spins on Gatsby. Like more than you can swing a cat at. So if you want, like contemporary spins on these characters, you can Google your way to at least a hundred of those. But some of the most interesting ones that I found. Keira Davis Lurie published a novel called the Great Man M A N N that is set in the same time period in the 1920s. But it remixes Gatsby as a story among a wealthy elite black Community in Los Angeles. There's Beautiful Little Fools by Gillian Kantor, which shifts the perspectives to the three women of the book, Daisy, Myrtle and Jordan Baker, whom we didn't really talk about much, but she's a golf player that is friends with Tom and Daisy.

[A]

I found myself very interested in her.

[B]

Yeah. And that Carraway sort of has a summer fling with her. Maureen Corrigan wrote a book called so We Read on, which is a play on the last line of the novel about, like, basically, it's what we talk about when we talk about Gatsby. And then there's an audible original called the Great Gatsby at 100 that came out this year that one of the Patreon folks recommended to me, that is six lectures from the Great Courses series about the Great Gatsby. So if you want to go more down the nerdy path, you could go there. But there are goodreads lists galore of books featuring the Great Gatsby characters. Remixes, new spins, perspective shifts, gender bending, race bending, whatever flavor you want to do that explores these characters and these themes. There is a twist on it. And I don't know that Gatsby is the most remixed. It probably is Shakespeare, but there are so many of these.

[A]

There's a lot. Yeah. I guess if you. If you go back a generation, it's not even a full generation, but if you go to Edith Wharton backwards a little bit in time. She's writing about high society in New York and the complications. Again, it doesn't have. It doesn't have the gin piece. It doesn't have the lemon and the. And the. It doesn't have the sharpness. I don't feel like it has sharpness, but it doesn't have this kind of sense of, like, it feels older. It doesn't feel modern in particular way.

[B]

The book is literally a. And spiritually is a car crash. You just kind of read the whole thing with your hands over your face, like, oh, my God, these people.

[A]

Yeah. Warden is sort of a midpoint between an Ostonian mode and a Fitzgeraldian mode, but I think it was like that too, at the same time, and deals with similar things. Let's get some of the sentences into the air. I've got a couple that I. My temptation is to spend five minutes per word on some of these. What did you single out as something that you noticed?

[B]

Oh, another good Tom Buchanan. One Tom Buchanan compelled me from the room as though he were moving a checker to another square. Just like, you know exactly what that move looks like when this Burly guy is trying to get you to go somewhere. I love. I was within and without, simultaneously enchanted and repelled by the inexhaustible variety of life. And what I thought that meant when I was 17 and what I think it means now are very different. On the practical tip, it's a great advantage not to drink among hard drinking people.

[A]

That is really good. Let's see what I have here. I mean, the kind of. There's a sentence that made me stop and think about it like there are only the pursued, the pursuing, the busy and the tired. I hit the tired more now than when I was 17. I was much more interested in the pursued and the pursuing. But the busy and the tired were very, very fascinating to me.

[B]

The busy and the tired would be a great memoir.

[A]

Reserving judgments is a matter of infinite hope. That's amazing. That's an amazing idea that. The idea of reserving judgment is a hopeful, optimistic attitude. And I guess the reason there is. Because it's not over, right? To withhold judgment is to suggest the story can trundle on and it's not

[B]

over that there's always the possibility that people will develop into something else.

[A]

Yeah. And then some of just beautiful. In his blue gardens, men and girls came and went like moths among the whisperings and the champagne of the stars. I mean, just pretty. Just damn pretty.

[B]

It is. There's a great description of Gatsby after Carraway has started to really understand who he is. That says. I had talked with him perhaps half a dozen times in the past month and found to my disappointment that he had little to say. So my first impression that he was a person of some undefined consequence had gradually faded and he had become simply the proprietor of an elaborate roadhouse. It's like, that's a burn.

[A]

That is a. That is. That is a real burn. And then like some of his descriptions, he's trying to capture something of Gatsby's character. Gatsby is not. He's trying to come into the interior of Gatsby. It's not just he's a guy who loved a girl. And that was all. I mean, that's. That's part of it. But listen to this. There must have been moments, even that afternoon, when Daisy tumbled short of his dreams, not through her own fault, but because of the colossal vitality of his illusion. It had gone beyond her, beyond everything. He had thrown himself into it with creative passion, adding to it all the time, decking it out with every bright feather that drifted his way. No amount of fire or freshness can challenge what a man will store up in his ghostly heart. That is something other than he had loved with a girl and couldn't get her.

[B]

And that was the next place I was going to go in my notes too. So we're on the same wavelength now that. Oh, also we should make sure to tell folks, Jay Gatsby is not Gatsby's real name. This is.

[A]

Oh, right, yes, it's a put on. Right. He was like a boatman. He met someone, inherited some money and he was off to the races.

[B]

His last name was Gatz and he has constructed this whole identity for himself. But Caraway sees it at some point that. So he invented just the sort of Jay gatsby that a 17 year old boy would be likely to invent. And to this conception he was faithful to the end. And like this vision of who he should be and how he thinks that he should show up in the world in order to get the things that he wants and to be successful and to eventually get the girl, like, this is the tragedy of him. It's a real kind of arrested development. But instead of saying like, he invented himself at 17 and he never grew, he gives us this beautiful. Like he conceived of this thing and he stayed faith. Like what a sentence.

[A]

Man, that's amazing. Yeah, I've got one big meaty one that I want to end with. Do you have anything else on your list?

[B]

Let's go to the big meaty one.

[A]

So I was saying before, like, the thing I found myself really taken aback by, which was Sheryl's interest, ability and commitment to capturing the seemingly ineffable quality someone has of a gesture or a mood or, you know, a visage. And this is Gatsby. This is him on Gatsby's smile. Just a smile. He smiled understandingly. Much more than understandingly. It was one of those rare smiles with a quality of eternal reassurance in it that you may have come across four or five times in life. It faced or seemed to face the whole eternal world for an instant and then concentrated on you with an irresistible prejudice in your favor. It understood you just as far as you wanted to be understood, believed in you as you would like to believe in yourself, and assured you that it had precisely the impression of you that you at your best had hoped to convey. Hot damn, Rebecca Schinsky. That is worth a novel.

[B]

That is worth a novel right there.

[A]

Most good writers would have done a tenth of that.

[B]

If you get one sentence like that in your entire career as a writer. You've had a win.

[A]

Well, it's not one sentence, right? Like in just the way that it rhythms and the builds and it goes from like. And it taps into this idea of like the idea of someone with a great smile and another writer might have said like it made you feel the way you wanted to feel and sort of moved on from there. But it's more than that, right? It's not like it knows what you know about yourself and affirms your wantingness

[B]

that Gatsby is smiling at you and you're seeing Gatsby smile at you and he's seeing you see him smile at you. And that this whole power dynamic is constantly moving and constantly calculating and behind that.

[A]

Is that. Can that possibly be a put on, right? Can that be faked? And if it can be fake, do I care if it makes me feel that way? I'm not sure. I'm not sure. Just a remarkable little bit of insight. Pillars of the Earth, understanding of humans talk, you know, being in relationship to other humans and doing the most fundamental sort of human thing is to smile. I don't know. I was completely blown away by that.

[B]

It makes me mad that someone who was like 27 when he started writing this book could achieve that kind of. Of observation too.

[A]

Like, you know, he really, in his early books, he was praised for this sort of thing. Right. But critiqued for construction and plot. And you can see him layering a more sturdy plot onto this. I'm not sure he would have cared about. I think the plot stuff is an excuse for him to do this. Like, I think this is what he cares about. That's my sense of what he cares about. And I think that's not a bad way of reading a book if you can kind of find what the author is caring about and lean in and really dig into those moments. Like, this is what they live for. This is what the book exists to sort of serve as a coat rack to hang a beautiful garment and one of the great descriptors of humans. Just amazing.

[B]

I think that's a great lead into the. So how do you know if you want to read this book?

[A]

I mean, if a likable character is a thing that you need, I would run away. You're not going to get that here if you need to understand because like there's part. Some of these descriptors, I don't feel like I can completely wrap my head, my head around like they kind of elude me in some way. And I find that to be tantalizing and affirming because there's a lot more for me there. You know, if you're a sentence lover, great. If you're less of a sentence lover, you may find it more trying.

[B]

I think those are both really accurate for what kind of reader you are. If, like me, when you're at dinner, you are eavesdropping on the people next to you and you know that the person you're dining with is doing the same thing. And then you're going to get in the car afterwards and be like, did you hear when they said this thing? And did you notice when that happened? This is a book for you.

[A]

There's a great line, I don't have it in front of me, about how large parties are much more intimate than small parties. Because at small, private, there's no privacy.

[B]

Yeah. Nobody feels like they're being watched.

[A]

At a big party, everyone's feeling watched the whole time. Really fascinating stuff in there. Yeah. Like, it is a novel of manners. But if you're interested in interpersonal dynamics like that, it can be pretty great. Again, even if you're like, I'm not sure if this is for me, the ask is not large.

[B]

Yeah. I think if you want, you have to be good with morally gray areas if you want an authority who's going to come down solidly on, these people are good, these people are bad. These actions are okay. These actions aren't okay. You will not get that here. There's a lot of ambiguity. And Caraway, as you were saying, tells us from the very beginning that he doesn't want to judge himself or these people. I think that allows him to spend time with them and observe them deeply because he's not interested in demonstrating how good he is by declaring that they're bad. But. But you do have to be able to roll with something like that if you're looking for a clear declaration from the author of his intent or his moral judgment about the characters or about what people should do. You won't get that here.

[A]

I think honestly, you won't find that in many of these.

[B]

Yeah, I agree.

[A]

You won't, because that ages well. It doesn't age poorly necessarily, but it's not continuing interesting. It doesn't have a fount of engagement. Yeah, I don't know that it lacks art necessarily, but there's no reason to return to it 20 years later. We are not in want of judgment, let's put it that way. Especially when it comes to interpersonal relationships or political. I do not find myself turning to art to tell me what I Should think morally about the universe. I think it's not ammunition necessarily. It's education. It's sensibility training for how to encounter the world. But, like, I've tried what's like, the most. The Inferno by Dante. Okay. Clearly about judgment. But the interest there is not the judgment. It's the art. Like, it's sort of the play and the inventiveness. Right. Like, it was just like, popes are bad. Like, yeah, Great news at 11. We can move on.

[B]

Popes are bad, so let's turn them upside down in baptismal fonts. It'll be funny.

[A]

Yeah. The variety, the inexhaustible variety of Dante's judgment is maybe the thing that talk about world building, like a lattice work, like the coat rack he cares about is in that. Well, we can get into it.

[B]

When we do Dante's story, we'll get

[A]

into the Inferno someday we'll get into Dante. What else to say about the Great Gatsby? Rebecca, did we leave anything that we'd be really pissed off about that encounter?

[B]

No, I just want to say if you're on the fence about it or if you haven't read it in a while, don't trust your teenage reading of this. If the last time you touched this book was high school, and if you've never read it and you're on the fence, tilt into. Yes, I think this one is worth jumping in. There's a reason that we started with it and not just because it's 100 years old this year and it makes a nice content hook. There is a lot to be found. There's a lot to talk about. There's a lot to wrestle with. And these characters are of types that existed in fiction before and that we continue to see in fiction and now we see in reality TV today. And being able to sort of map how that all works and how artfully Fitzgerald does it into the ways that you read contemporary work or that you. We sometimes talk about how you read a movie or how you read a TV show is, I think, really valuable. And just being able to recognize, like, this is a Gatsby sort of archetype. This is a Nick Carraway kind of archetype, is really valuable. And that's another reason for us to take that we're taking this project on is that these books are valuable in themselves, but also they speak to each other over time. And having a grounded understanding of. Of what happened in a book 100 years ago that someone's referring to in a book now also makes you a more well rounded reader.

[A]

Yeah. And you can also correct the reference.

[B]

Right.

[A]

Like you can see how it's maybe a facile or surface level reader understanding. I think that ends with us today. Bookriot.com Listen, we can find the show notes there. I don't know that we have a bespoke email yet, but we always can. Find [e-mail], we'd really like to hear feedback about structure, which pieces of a show like this is going to be more or less interesting. What do you find more on? We will of course take recommendations for things to cover. I would temper your expectations about the timeliness of responding to that.

[B]

The master list for this is like 400 books long. Yeah.

[A]

Rebecca, thank you so much all this morning.

[B]

Yes and zero to well Read is a proud member of the Airwave Podcast Network.