The Great Gatsby by F. Scott Fitzgerald

24:25Set each other up and have these really awkward social engagements and permutations that I'd be like, I would run. That's how I know Carraway's not really a Midwesterner. He would never... I mean, that's a joke.

24:36Jeff:100%. Carraway 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 the love nest that Tom keeps with Myrtle. Along the way, she stops and buys a puppy for like unknown reasons. And 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.

25:13Listen, I have this one for you. I've been saving it. I'll use it here. Alternate title, Crazy Rich Caucasians.

25:20Jeff:it really is it really it really is 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 but which drunk which is always helpful for these kinds of encounters 100 degree no air conditioning remember it's 1922 or something 528 yeah 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.

26:14Jeff:Like, it's not sufficient that Daisy is in the moment. It's the real climax of the book, right? This moment where Daisy admits that 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 what happens in. 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.

26:51Jeff: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 End. And they don't have anti-elect 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.

27:26Let's just say the 1920s is not the time you want to be flying back and forth from Long Island in New York City on the highway.

27:32Jeff:There were no highways, there were just roads. In one of the great coincidences of fiction, which you get to do if you can pull it off the way of 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. Things are going great with the Wilsons. And just as she's 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. It's truly a hit and run.

28:06Jeff: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. 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 the series have achieved this iconic status, which actually blinds culture from seeing them directly.

28:51They become a totem of themselves. And the Gatsby, we talk 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-themed party is out there of the music and the ambiance and the clothes.

29:12Jeff:The flapper dress and the long cigarette holders. And this sort of ironical pose. 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. We can get to our own reactions and 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 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.

29:46Jeff:That was also astonishing to me 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's 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 yeah people just show up to his house because they're not interested in him they just all want to be at the party and he has the scene yeah 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 it's just a huge house of cards built on a lot of assumptions that Gatsby has made.

30:51Jeff: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 twenties. And I had a lot of thoughts about like the mid twenties ain't what they used to be. 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 Carraway's observation, and this is maybe to my mind, I'm not going to speak for everyone who's ever read Fitzgerald.

31:32That'd be too much, Rebecca, I think, to try to do. To my mind, one of, if not Fitzgerald's greatest skills is, or projects is to try to describe the ineffable something of someone, right? In talking about 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?

32:24Or 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 juriate on.

32:33Jeff: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 New York. I think that outsider-ness, you know, you have to be from somewhere else to see that this is the water. 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 met Zelda Sayre, who would become his wife. But she initially rejected his proposals because he didn't have any money.

33:14Yeah, it's in there. I mean, it's just that's not even subtext. It's just text.

33:17Jeff:So this is where Gatsby gets the idea that he needs to look like 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. It's just that outsider perspective, I think, really, really matters here. And 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.

33:57Jeff:Fitzgerald dies in 1940, at the age of 44. And at that time, he thinks that the book is a failure. 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.

34:31And so 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 Echelberg and Perkins and Fitzgerald.

35:10Perkins writes to Fitzgerald and says, you've got this great metaphor. They're talking about the metaphor in it. And it's just on the page. It's so weird.

35:17Jeff:I remember, I will know the eyes of Dr. T.J. Echelberg 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 mentioned it like three or four times that it's - But a metaphor that's mentioned three times is kind of weird for a book like this. That it's that, that is, it is that 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.

35:46Jeff: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. Like he's dramatic, maybe. I mean, I think he probably tended to the dramatic. 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.

36:27Jeff:Did they fall out of favor because culture was shifting and perspectives on wealth were shifting? My reading of it is most books fall out of favor. Yeah, your base case is that falls out of favor. Right, but Fitzgerald dies believing the book is a failure. 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.

37:08Jeff:And Great Gatsby has been Scribner's bestselling book of the year basically every year since then. It's incredible. It really made Scribner, and then Scribner, which became part of Simon & 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. It's a brand as much as an actual book. That's the sound of zero sugar, 200 milligrams of caffeine, and the power to burn body fat. Storm Energy Blend helps boost metabolism, which in combination with exercise and a healthy diet helps burn fat.

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38:22Jeff:This product is not intended to diagnose, treat, cure, or prevent any disease. This episode is brought to you by Facebook. So you were scrolling on Marketplace, and there it was, the bike you'd been searching for. You sent a message, and it turned out the seller was super chatty, kind of funny, and an avid cyclist. The next thing you know, you're in a cycling crew. well, a community cycling group. The thing about Facebook, you might find more than what you're looking for. From a browse to a bike ride, this summer, find more on Facebook. 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.

39:08I was not assigned in high school. I wrote it in high school.

39:10Jeff:Oh, wow. Okay. Is that I was sort of tackling one of 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. Yeah. But other than that, I've got no sense memory. I think I even got a couple of the plot points wrong, but there's still a lot there. And 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.

39:50Like Tom calls him out, where did you get that, man? What are we doing here? 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. that's very small, in which Nick Caraways 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.

40:13Jeff:Someday she'll come over and this is the thing that's going to make her love me. And so there's this bespectacled old guy sitting in the library being like, 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 is now cosplay is so mind-blowingly perfect or terrible that it's kind of hard for me to get my head around.

40:54Jeff: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, if you've seen deckled edges on a book, that is now 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 not decorative. Symptom, not the cause. Right. Yeah, I think I definitely did not grasp how sad this book is and how depressing Gatsby's life is when I was in high school.

41:37Jeff: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. Echelberg. The green light at the end of the doc? I mean, some of that stuff I remember. I mean, I absolutely wrote an essay about what the symbolism of the green light at the end of the dock. That's what we have LLMs for. Right. I mean, honestly, like, okay. And I remember 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.

42:16Jeff:And that, you know, one would be like very straightforward word language and short sentences and the other would be Fitzgerald. And I think that in the 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. Like I think some of the slang would have felt timely and it feels, you know, old and like a mark of its time now.

43:04Jeff:But this was like, I didn't, 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 wanted to, I was a nerd. So I wanted to understand why it was important. You wanted the gold star for having read yet. 100%. I wanted to be able to show up at the cocktail party and explain the meaning of the green light. 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, first of all, I was like, hell yes, this book is 200 pages long. 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 yeah and that flat i mean i think the flowery i hesitate to well here can we reclaim flowery Yeah, let's reclaim it.

44:08Let's reclaim it. Flowers are great. Yes. I love flowers. Again, in looking at a whole bunch of art museums, the idea of capturing the specificity and ornateness of kinds of flowers is really cool. And it's not purple prose, though. It's not. I think that's what it is. He's using unusual. I had to, quote unquote, stop and consider, what is going on with this? What is this description? What is going on with this? There are words I don't remember ever knowing before. Pasquenade, 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.

44:44And 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, 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? form whereas Fitzgerald's like painting every single wave and he's like trying to do something it's a very mannered I guess is maybe a way of putting it I think I find it very rich and stimulating me too I found it to be a really literary method of world building like this is

45:19Jeff: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 complicated or how the money works or how much everything costs or where it came from 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 to walk through it gives sort of experiential articulation right yeah i got the i get that yeah you i can feel that you feel like if you want if you were to just be dropped 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 yeah you know the the rootlessness the aimlessness right of the people who have 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 that would ever make anyone happy either.

46:34But 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 Very frankly, I don't want to talk about cancel culture at all, but what I do want to think about a little bit is how Carraway vacillates his viewpoint on the people that he's encountering. Because there's no good character.

47:15Oh, no. And even the monster is Tom Buchanan, what Tom Buchanan represents, I think, pretty clearly. but even Tom Carraway 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 Tom 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 scats but this weird articulation of 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.

48:00So this interplay of the past and the present, and how much someone is accountable for their own actions, but how someone 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 wildly helpful as a person in the world. And Caraway wrestling with that and saying, but for some people, I do you 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

48:32Jeff:know 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 Gatsby's life is pretty fake and pretty hollow to recognize that Gatsby's involved in some shady financial dealings?

49:11Jeff: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 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. Everything is very compact.

49:49Jeff: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. Like 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, sets the table for that really beautifully. I mean, 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 100 years ago, how much does our contemporary sensibility or contemporary truths or understanding do we bump against things that are representations here?

50:42Worldviews, isms of various different kinds, this is not without, I mean, I think probably Meyer Wolfsham is probably this Jewish criminal figure, right? So he has his own complication, right? Like I tried to make it clear to someone I'm their friend whether they're alive or other 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 even sort of hulking mass and how he's put together and how he presents himself to the world.

51:18He 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, like, Tom's gotten very serious. It's like, 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 seems a buffoon right away. And this is sort of a ridiculous position to hold.

51:42Jeff:From the first scene with him, you know that if we ported him into 2025, We know exactly which websites and cable news networks Tom would be reading. One of my favorite lines in the book, one of my favorite descriptions was Carraway describing Tom as one of those men who reached such an acute limited excellence at 21 that everything afterwards savers of anti-climax. Bro peaked in high school. Peaked in high school is 100 years old. It was Fitzgerald the first person to do a peaked in high school 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 awkward to me I would say that these clownish buffoonish figures that seem to be the first inclination is to create them as an object in ridicule can still backhand you and break your nose as he does later on the buffoonishness is terrible it's King Kong with a clown wig because it can still wreck your life, wreck the city and wreck the world and that's where Buchanan is and his desire his designer of ownership is a twin of Gatsby's desire for ownership.

52:47Compared 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 soulmates, and they love forever, and they can't have loved everyone else, and everything else would be perfect. That view is very much positioned as an engine of destruction. Yeah. 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 in the book. That's not the way to be.

53:25That's going to lead to tears and death, frankly. And I found that to be pretty shocking to encounter here again.

53:31Jeff:Yeah. Jesmyn Ward wrote the introduction in the paperback copy 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 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.

54:12Jeff: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. 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 representation of wealth, right? It's hard to... I mean, I think that's one of the neat tricks Fitzgerald also pulls off is that you kind of want to spend time in the rooms, right? 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...

54:46I mean, 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 there are 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.

55:05Jeff: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. This is a tale as old as time. It's a trope that artists have been visiting and revisiting and probably will be. If we had sort of a how does it hold up in terms of a modern sensibility scale? Remarkably well, I would say. It's certainly not going to map neatly onto everything that sort of a left-leaning literary person, as we are, are going to bump up against. 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.

55:55I did think it's funny you have in the trivia here that Carraway doesn't come out and say he hates phonies, but he's on phony watch. And that is very Holden Caulfield coded, I would say, at this point. And it's mentioned in Catcher in the Rye that it was a favorite of his... Like, mentioning Gatsby to someone, you know, someone like Salinger, like, he was a person who would have maybe read this as 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 Carraway, of, like, trying to learn about the world and how to be a little bit later in life that Caulfield is representing in Cajun.

56:43Jeff:Yeah, most of the things that Carraway observes these people do, like this is a cautionary tale about how not to live, which is the whole point that Gatsby's life looks like the life that 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.

57:19Jeff: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. Well, I think this, Rebecca, 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.

57:58Like I'm bastardizing, you know, Mark. The root of all evil. I 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, 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 Sinclair expose because Carraway is adjacent to it. And, you know, he's a bonds trades person. It's not like he's a brick worker 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.

58:41Jeff:Yeah, and he's so good at showing that he doesn't have to tell. Yes. And I think that's what Fitzgerald is sort of most, and this is true in This Side of Paradise and The Beautiful of the Dam, he's sort of interested in the crackling air between two people who have a complicated relationship. 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 and trying to capture the feel of it, the experience of being in those rooms. In doing that, I think he kind of maybe comes into 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.

59:28They're not interested in anything. They're not interested in anything. It's all an ironic pose and positionality.

59:34Jeff:Yeah, it's that they're not interested in anything, that there's nothing here. It's all edifice. They're looking for the next party. And again, if you're putting this in a larger context of World War I, 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, it 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. I was at the battle line.

1:00:10I 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 like no one goes to church anymore which they talk about no one showing up they don't seem to be interested in philosophy or art or anything else like that they don't even cut they know enough to buy the library to show the thing but they're 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 this is one of the great polls you have here tell me about the most modern reference to careless so sarah winn williams who wrote the

1:00:45Jeff: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, 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. As an age of day. No. As an age of day. On the adaptation fronts, I would say, I'm not going to spend much time on this, all of them unsatisfied. They all have terrible tomato ratings.

1:01:22Jeff: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. I'd heard of it. I haven't seen it. 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. This has been adapted. And there are a couple others.

1:01:54Jeff: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. Yeah. Yeah. So if you've ever wondered F. Scott Fitzgerald and Francis Scott Key, yeah, they are related. Fitzgerald was named after Francis Scott Key, who, of course, wrote the national anthem. I didn't know you got rejected titles here. Let's just say they've landed on the right one. F. Scott Fitzgerald, shitty at titling books. You don't think the gold-hatted Gatsby would have been better?

1:02:29Jeff:Among the ash heaps and millionaires? A high-bouncing lover really is an avoided 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 a person. Trimalchio was a character in Satiricon 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. We would not be sitting here in 2025. Maybe Trimalchio in 2025 was like saying Romeo. I mean, I had to look it up again. I think that's a literary character, but that was a real bad one too.

1:03:15I mean, The Great Gatsby, this is one of my hot takes here.

1:03:18Jeff:I love this. 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. One of the pieces I read researching the show today referred to it, like, think about it as a magician, you know, the great Gatsby. Gatsby the Great maybe captures the weirdly just moving the definite article around, I think captures a little bit more.

1:03:54That's a really good point but like 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 he's really successfully created the illusion the illusion but is you know 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 20s to the point where he became a legendary and mythic figure by creation and accident at the same time. Pretty amazing at this point.

1:04:35Rita likes.

1:04:37Jeff:This feels so singular to me that I really struggled with Where Do You Go? I don't have a good one. I really don't. 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. I like the Unbeautiful in the Day. I like them all. And those are great book titles also. Like what happened to him when he got to the Great Gatsby? Well, those are all pulled from Shakespeare. So I'm pretty sure. Hemingway did it too. They both were pulling for Shakespeare a title that For Whom the Bell Tolls, Farewell to Arms.

1:05:09Those are amazing. You know why? Because the Bard wrote them.

1:05:11Jeff:And see above, read. You don't have to read anything except maybe you do have to read Shakespeare. Yeah. I went looking. 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, Kira 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.

1:05:48Jeff:There's Beautiful Little Fools by Gillian Cantor, 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. I found myself very interested in her. And that Caraway 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, 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.

1:06:26Jeff:So if you want to go more down like the nerdy path, you could go there. But like, there are Goodreads lists galore of books featuring the Great Gatsby characters, remixes, new spins, perspective shifts, gender bending, race bending, like 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. There's a lot. Yeah. I guess 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.

1:07:08Again, it doesn't have the gin piece. It doesn't have the lemon 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... It feels older. It doesn't feel modern in this particular way.

1:07:22Jeff:The book, literally 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. Yeah, Warden is sort of a midpoint between an Austonian mode and a Fitzgeraldian mode, but I think it was like that too at the same time and deals with similar things. Class is now in session. And the UPS Store is here to help you ace arriving on campus. Our certified packing experts can pack everything you need, from desktops to decor. Plus, when you pack and ship with us, you get our exclusive pack and ship guarantee. Your items arrive safe or your money back.

1:07:59Restrictions and limitations apply. To get a 20 % off packing coupon and for full details, visit the upsstore.com slash packing. Let's get some of the sentences into the air. I've got a couple that I, you know, my temptation is to spend five minutes per word on some of these. What did you single out as something that you noticed?

1:08:21Jeff: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. 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.

1:09:04Like, 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.

1:09:18Jeff:The busy and the tired would be a great memoir. Reserving judgments is a matter of infinite hope. That's amazing. That's an amazing idea. 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 over. That there's always the possibility that people will develop into something else. Yeah. 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, that's just pretty.

1:09:56Just damn pretty.

1:09:57Jeff:It is. There's a a great description of Gatsby after Carraway has started to really understand who he is. It 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. 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...

1:10:34He'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 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.

1:11:09That is something other than he in love with a girl and couldn't get her.

1:11:12Jeff:And that was the next place I was going to go in my notes too. So we're on the same wavelength now that also we should make sure to tell folks, Jay Gatsby is not Gatsby's real name. This is - 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. His last name was Gatz. And he has constructed this whole identity for himself. But Carraway 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.

1:11:52Jeff: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, 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 sentence list? No, let's go to the big meaty one. So I was saying before, like the thing I found myself really taken aback by, which was Cheryl's interest, ability, and commitment to capturing the seemingly ineffable quality someone has of a gesture or a mood or a visage.

1:12:26And 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 impression of you that you, at your best, had hoped to convey.

1:13:04Rebecca Shinsky, that is worth a novel. That is worth a novel. Right there. Most good writers would have done a tenth of that.

1:13:12Jeff:If you get one sentence like that in your entire career as a writer, you've had a win. Well, it's not one sentence, right? Like it's in just the way that it rhythms and it 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've 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. 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.

1:13:49And behind that is that, can that possibly be a put-on? Can that be faked? And if it can be faked, 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 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.

1:14:19Jeff:It makes me mad that someone who was like 27 when he started writing this book could achieve that kind of observation and perspective. Well, Fitzgerald too, 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. 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, ah, this is what they live for.

1:15:03This is what the book exists to sort of serve as a coat rack to hang a beautiful garment. And what are the great descriptors of humans? Just amazing.

1:15:12Jeff:I think that's a great lead into the, so how do you know if you want to read this book? 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 there's some of these descriptors, I don't feel like I can completely wrap my head around. 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. I think outside, I think those are both really accurate for what kind of reader you are.

1:15:51Jeff:Like, 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 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? Like, this is a book for you. Yeah. 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 privacy, there's no privacy. Yeah, nobody feels like they're being watched at a big party. Everyone's feeling watched the whole time.

1:16:19Really fascinating stuff in there. 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.

1:16:31Jeff:Yeah, I think if you want, you have to be good with morally gray areas. If you want an author 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, you know, 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 you do have to be able to roll with something like that.

1:17:05Jeff:If you're looking for a clear declaration from the author of his intent or his moral judgment about the characters, about what people should do, you won't get that here. I think, honestly, you won't find that in many of these. Yeah, I agree. You won't, because that ages, well, it doesn't age poorly necessarily, but it's not continuing interesting. Like, it doesn't have a fount of engagement. I think it lacks art. Yeah, I think, I don't know that it lacks art necessarily, but there's like 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, you know, interpersonal relationships or political, like, I do not find myself wanting, turning to art to tell me what I should think morally about the universe.

1:17:48I 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 11, we can move on.

1:18:08Jeff:Popes are bad, so let's turn them upside down in baptismal fonts. Yeah, right. It'll be funny. Yeah, the variety, the inexhaustible variety of Dante's judgment is maybe the thing that, talk about world building, like a latticework, like the coat rack he cares about is in that, well, we can get into it when we eventually get 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? No, I just want to say, I think 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.

1:18:47Jeff: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 being, just being able to recognize like this is a Gatsby sort of archetype.

1:19:32Jeff:This is a Nick Haraway kind of archetype is really valuable. Like, 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 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. Yeah. And you can also correct the reference, right? You can see how it's maybe a facile or surface-level reader understanding. I think that ends with us today. Bookriot.com slash listen. We can find the show notes there.

1:20:08I don't know that we have a spoke email yet, but we always can find us at podcast at bookbriot.com. 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 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 them.

1:20:27Jeff:The master list for this is like 400 books long. Rebecca, thank you so much. Yes, and Zero to Well Read is a proud member of the Airwave Podcast Network.