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Jack Wilson
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Jack Wilson
Hello, the 25 greatest books of all time. What are we even doing? Mike Palindrome joins us for a discussion today on the history of literature. Okay, here we go. Welcome to the podcast. I'm Jack Wilson. It's nice to have you here. It was a great idea. When I started, it was 20, 25. That's a couple of nice round numbers. And halfway through the year, I thought, let's do something to celebrate. How about 25 books? The best 25 books of all time. The greats. Why not? Well, here's a reason why not. Who gets to choose such a list? Me. I would ordinarily rise to the challenge, but I thought, well, is that really great for listeners where they get to hear all about Boswell's Life of Johnson again and James Joyce's the Dead again, and on and on? Me, me, me, me, me. Chekhov, you know, all my favorites. So I thought, well, I'll find a list. Find one that others have done. But what list do you choose anyway? You know, any kind of selection is going to be subjective. So I go through all of this with Mike, how I wound up with the list that I used. So I won't repeat it here, but suffice it to say, it's a list that raises as many questions as answers. The 25 greatest books of all Time. I found a list and I used it. I'll explain why, and Mike and I will go through some of the shortcomings. And there were. I kind of stopped at the top two because I wanted to do special episodes for those. So I will announce those, but I haven't yet determined the order. Figured I could tweak that list that I used a little bit if I wanted. But Mike confirms my thinking. We will announce the top two in this episode. Okay. A list that raises as many questions as it answers. Is that the nature of all lists. Well, not really. You can have lists that are fairly well defined, the 25 most common elements in the universe. For example, you could have a list like that. You might be wrong, but it's not in dispute. You can measure, you can assess where you're wrong. But for something like books and what greatness is and which book is great, that's not really measurable. You could try to measure it by some criteria. The most sold or the most popular. The longest. Like the longest lasting popularity. Anyway, your selection of criteria is already subjective. The most meaningful. What does that even mean? So. And yet we love lists. I'm not a big fan of Harold Bloom, but when he makes a list, I read it. I might disagree. But I also discover, I challenge, as my hero Dr. Johnson might say, it calls forth all my powers. So Mike will be here soon, and then we'll do a My Last Book with Cass Sunstein. There's someone who was very decisive about the last book he would choose. And spoiler alert, it's not one from our top 25 something new. But first, there's a literary controversy that I wanted to share with you. I enjoyed this. We've been reading some T.S. eliot lately, and we fell into a little rabbit hole of somebody who misunderstood T.S. eliot and maybe shouldn't have. I love this kind of repartee among literary giants. In this one, it's T.S. eliot taking on Henry James and Gore Vidal years later coming to James's defense. But was Gore Vidal inventing a controversy that wasn't actually there? Let's hear the story. Does anybody here. Anyone here ever here, as if we're all in one big room together. Raise your hand if you. I shouldn't say anyone here. I should say, have you. Have you ever watched the show Three's Company? There was a joke in the 80s after Three's Company had been the number one show for years. The joke used to be, oh, yeah, Three's Company. Did you ever see the episode where there's this incredible misunderstanding? And the joke was. That was the joke every time. That was the premise of every episode, that somebody would overhear something, mishear it, maybe the landlord, Mr. Furley or Mr. Roper. They would misunderstand something and things would turn farcical. So here we have a misunderstanding like that. I guess in our analogy, T.S. eliot is our Jack Tripper, and Henry James is going to play the part of Suzanne Summers, Chrissy, I guess her name was, and Gore Vidal. He's coming in as Mr. Furley, the nosy landlord. Played by Don Knotts. And this is the kind of trenchant literary analysis you can only hear at the History of Literature podcast, people. Anyway, let's hear Gore Vidal. This is in the New York Review of books from 1986. I have never understood T.S. eliot's Wisecrack that Henry James had a mind so fine that no idea could violate it. In James, one is always aware of a highly subtle intelligence with all its changing biases and viewpoints as it considers everything from Communism to. To D.H. lawrence. I, on the other hand, have never detected much in the way of ideas, as opposed to moods or prejudices in Eliot's curious, neurotic commentaries. But then Eliot ended a mere Christian. James ended an artist, end quote, A wisecrack, Vidal says. And then he kind of basically says he prefers Henry James to T.S. eliot. And he doesn't get Eliot's wisecrack. He's implying that Eliot isn't a thinker on a par with James, and maybe that Eliot couldn't quite get James, that he insulted James. He overlooked Henry James's intelligence. He dismissed a superior mind with a wisecrack. David Womersley, an upcoming guest on the show, pointed out in his book that there's a context of the quote where it's clear that Vidal is misreading T.S. eliot. I'm going to abbreviate the full context of the quote a bit here. This is what TS Eliot actually said about Henry James. James, critical genius comes out most tellingly in his mastery over his baffling escape from ideas. A mastery and an escape which are perhaps the last test of a superior intelligence. He had a mind so fine that no idea could violate it. In England, ideas run wild and pasture on the emotions. Instead of thinking with our feelings, a very different thing. We corrupt our feelings with ideas. We produce the public, the political, the emotional idea, evading sensation and thought. Mr. Chesterton's brain swarms with ideas. I see no evidence that it thinks. James, in his novels is like the best French critics in maintaining a point of view, a viewpoint untouched by. By the parasite idea. He is the most intelligent man of his generation, end quote. So, in other words, Vidal was looking at this snippet. He had a mind so fine that no idea could violate it. And saying, huh, Elliot must think James is dumb. And instead what Elliot is saying is that he's talking about ideas the way we might say something like cliches, the way we might say, oh, he can't think an original thought. He's just got all of these prepackaged ideas. That are running around his mind. And what Elliot admired was that James's thinking could not be violated in the sense of being attacked or seized or taken over or abused, where the ideas become a crutch or a replacement for thought. And you don't need to think your way into something new. You settle into a little cubbyhole that's already been thought for you. Sometimes we say, sometimes we say perceived, no received ideas or conventional wisdom, except maybe on a scale of talking about politics or systems of thought. That cubbyhole that you're in is an idea. Capital I. James, in other words, had an intelligence that could absorb those ideas, but go on thinking. His intelligence did not settle. And it's clear Vidal didn't read the whole paragraph, because he says in there, he says it's the last test of a superior intelligence, and James passed it. And he says he's the most intelligent man of his generation. So clearly he's not saying he's too stubborn to think of an idea. So. But I'll miss this. It's a nice quote, very memorable phrase, idea mind. So, fine, no idea could violate it. But it's easy to misread if you're just reading one sentence instead of the whole paragraph. And luckily, in 1986, readers of the New York Review of Books were ready to defend Eliot's remark. They knew even the lordly Gore Vidal could be educated. And I mean that in a couple of ways. Both that people were available to educate him by pointing out that he had taken this out of context, but also that Gore Vidal himself was not above being educated, which he remarked upon in his own witty and, one might say, wisecracking way. So his review comes out in November. By December, the New York Review of Books was running this letter. Quote to the editors. T.S. eliot's supposed wisecrack about Henry James is actually a compliment. Context Herewith, I think Mr. Vidal might enjoy it. And the author of the letter then quotes the passage that I quoted to you, signed Eleanor Cook, Victoria College, Toronto, Ontario, Canada. Gore Vidal replies, although, like the late Lord Mountbatten, I have never been wrong. My memory is no longer infallible, to put it mildly. And then he goes on to say that he's in Eleanor Cook's debt for quoting Elliot in full, acknowledges his mistake, and makes a few more jokes about Eliot, and that's that. All of this, this exchange, by the way, this is the kind of thing that used to blow me away. I started reading the New York Review of Books at college. I. I used to pick it up in the main reading room at Harper Library at the University of Chicago. There was a little area with comfortable chairs and all these newspapers and magazines, and somehow it was sort of a place to take a study break from the Kant or whatever you were toiling through at the tables. Somehow I stumbled across the New York Review of Books, which I've now subscribed to for decades, but it blew me away. Back then. How did people know all this stuff? How did they know enough to misread someone and correct a misreading and then politely acknowledge the point with a witty remark? How? There was no secret. They just read books. There's stuff in there to know and to learn. You just have to open the covers and read, and you have to choose the right things to read. Which is where a list of 25 greatest books of all time comes in. They might not be the 25 greatest, that's subjective. But I'll tell you this, they are great books, each and every one. There are no skips on this list. Mike Palindrome after this. Hey folks, when I started this podcast, it seemed like I had to figure everything out all on my own website hosting platform, scripts, recording, editing. When you're trying to build something new, your to do list can quickly become overwhelming. 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Pepsi wild cherry and cream treat yourself. Okay. Joining me now is our old friend Mike Palindrome, the president of the Literature Supporters Club who wears the term highbrow like a badge of honor. Mike, welcome back to the history of Literature.
Mike Palindrome
Thanks, Jack.
Jack Wilson
So I'm not sure you've been as fired up about a topic since the episode on whether Bob Dylan should have won the Nobel Prize. Are you ready to go?
Mike Palindrome
Yes, I am.
Jack Wilson
So I wanted to give a little bit of background about the list. This was halfway through the year 2025. I was looking for ideas for little things I could insert into the podcast, different content generation ideas. And I thought, well, here we are, 2025, nice round number. Why not do a top 25 for the year 2025? And then I thought, well, if I just choose my favorites, I'll probably just be repeating myself because those are the books that I talk about all the time on the podcast anyway, so I should branch out and see what other people have chosen, try to find some objective list. And I thought, well, whose list am I going to use? Even selecting a list would be subjective because every list has got some bias to it. If I chose a particular author or a particular newspaper or something, that would be kind of biased. So I found on the web this list of lists. It's kind of like the rotten tomatoes for books. And it compiled over a hundred lists of great books or great novels or reader surveys of their favorite books or lists published by places like the BBC or Penguin or places like that. And then they weighted the list according to some criteria. And I thought, okay, fine, we'll use this list. But then as I was going through, you know, I just pulled the list and pasted it into a document. And then as I was going through the list and really, really thinking about it, I started feeling like it was a pretty good list, but not great. And it has some major flaws that I didn't notice at the beginning, probably due to the methodology. So before we begin, and we're going to look at each of these selections on this list of 25, but before we do that, do you have any general comments about the list, things that you noticed?
Mike Palindrome
I have so many comments.
Jack Wilson
Okay, start us out.
Mike Palindrome
You know, I was thinking about how the predominance and popularity of lists generally in our society, and I kind of blame US News and World Report for starting it all with the college list.
Jack Wilson
College list, yeah, yeah.
Mike Palindrome
This whole idea that, like, is Johns Hopkins ranked three places in front of Cornell, like, and I used to ask, do we? Do we effing care? And apparently we do. We do care. We care about. Did Johns Hopkins move up the charts last year? Have they held their place?
Cass Sunstein
I mean, Yep.
Mike Palindrome
There is something that lists what I think of as they keep allow us not to think and feel justified in
Jack Wilson
not thinking and make us feel comfortable with a kind of false sense of definition. If you have a top 25 list of books you can kind of scan it and say, well, I've read 17 of these, so that's eight to go and I'm doing pretty well. Or, you know, it gives you this false sense of security, that there's something that is really hard and complex, but somebody has nailed it down.
Mike Palindrome
But the flip side to that is that the sports obsessed side of me loves the idea and the cruelty of one team besting the other. And like I said, think of Major League Baseball. You know, most generations grew up with the wild card, but you and I were probably the last generation without a wild card. And there were two divisions to each league. The American League had two divisions. The National League had two. And if you finish second, there was no wild card place. You finished second by a game.
Jack Wilson
Right.
Mike Palindrome
And to me, that really, you know, I perversely think it's great. So if you want to rank things, I'd probably play the game too, if I was asked to rank.
Jack Wilson
But look at college football. I think that is worse than it used to be. It used to be you could have a great season, maybe finish nine and two or something, and then you'd win a bowl game, maybe you'd win the Rose bowl if you were in the Big Ten or the Pac 10, and you'd feel like, this was great. We had a great year and we finished on a high. We won the Rose Bowl. And then they said, well, no, we kind of want to have a national champion and we'll. We'll make this playoff games. And it ends up being. Everybody feels like a failure except for the very final team standing. And I think it's kind of diluted the fun of college football.
Mike Palindrome
Yeah, I mean, I, again, I blame US News like War and Peace versus Anna Karenina. Is there really. Is there really anything worth talking about there?
Jack Wilson
I mean, here's the one thing that I thought is kind of valuable about this, which is sometimes you'd hear somebody say something like, oh, Patrick Ewing, he. He must be a top 10 player of all time in the NBA. And then you kind of say, well, okay, but who's. Who's ahead of him? And you start naming players. Michael Jordan, LeBron James, clearly and well, Larry Bird, Magic Johnson. And you get to 10 pretty fast. And then you realize, oh, what was I talking about? Patrick ewing. Maybe he's 20 or higher. You know, you have to. So it kind of does give you a sense when you're saying something like, you know, catch her in the rye. This must be the. This must be in the top three books of all time. And then when you actually make your list, that didn't even end up making my top 25.
Mike Palindrome
Yeah.
Jack Wilson
So a couple other things that I noticed about this list as I was going through it, and it's probably due to the methodology of a lot of these being reader surveys, is most people don't read thousands of books, and they probably don't even read hundreds of books. Maybe they read 10, and, you know, 10 great. 10 books that could be considered great. And five of those are probably assigned to them in high school or college. So books like the Great Gatsby and the Catcher in the Rye and the Grapes of Wrath, books like that can really overperform just because people aren't going to vote for a book that they haven't read unless they have some reason to believe that it's great in some way. So you end up getting, well, this is the best book I read. And you kind of reach back and you remember, well, we did. I remember that year that we read this book in high school. And that ends up being higher on the list than it probably would be if you asked some great critic to come up with a list of top 25.
Mike Palindrome
Yeah, I had the same thought. I mean, I was like, why not make a list of the top 25 books you were forced to read, like Of Mice and Men,
Jack Wilson
Animal Farm. Yeah. The other thing is, people seem to think that a great book has to be a novel. I mean, on the top 25, there's no Shakespeare, it's novels, and then the Odyssey and the Bible. That's it. There's no poetry other than the Odyssey. There's no short stories, there's no plays. There's no nonfiction or other religious books other than the Bible. Like, that feels like a huge absence to me. And people, you know, if you were really making a list and you had to pull a bunch of scholars for the most influential books or that kind of thing, you'd probably have some books of philosophy on there. You'd have Darwin. You'd have a lot of candidates that even seem to really get recognition just because people are thinking, great book, must be big, thick novel.
Mike Palindrome
Yeah. Le Monde, the French newspaper, does a ranking of the top 100 books and that I think Kant is always, like, in the top 20. They redo it every year.
Jack Wilson
And another thing I noticed is it's tricky for authors. It would be interesting to rank the top 25 authors because Dickens, for example, is not on here. He probably kind of split his own vote. There's probably four or five books that could have made it on here. If he had one that stood out among all the others as being the very best, that might have been higher. He might have been up there. Or Virginia Woolf is another one. I don't know which of her books. She probably had three in the top 50 or something. But to make it into the top 25 is harder. If you're not sure if it should be to the lighthouse or Mrs. Dalloway,
Mike Palindrome
I think it's one of the. There are some glaring misses to the list, but definitely to the Lighthouse for me.
Jack Wilson
Yeah. Okay, so I'm going to talk about the conversation we had leading up to this, because I could tell that the list, as you saw it, was steering you in a very particular direction when we started this. So the reason why I wanted to do this episode is because I have revealed numbers 25 through number three. I've left two that I didn't have time to do in 2025. And I also kind of wanted to give them a longer treatment than just part of an episode. I wanted to do a full episode, or maybe I haven't decided yet. Maybe I'll do multiple episodes and that kind of thing. So. But I did want to talk to you about the list because I thought that would be fun. So I. In setting this up, I texted you and said, okay, 25 through 3, I'll send you that. I'll let you guess the last two, which I figured you'd do right away. And then. Oh, and also I decided I could pick one and two. I wanted to get your thoughts on which one should be one and which one should be two. I haven't adjusted the list in any other way except once I screwed up and I did one too early, and then I didn't want to rerecord the episode, so I just flipped the order of two. And then I regretted it because it ended up putting Moby Dick behind the Sound and the Fury. And I thought, no, Moby Dick is a better book than the Sound and the Fury. So I didn't tamper with the list otherwise. But I did think, well, for number one and number two, we can talk about that. So I said to you, why don't you guess the top two? I'm sure it'll be easy, and then we'll talk about it. And I think the problems that we've talked about with the methodology of this list lulled you into a lapse. You guessed one of the top two right away, and you never did guess the other one. You guessed a lot of other books And I could tell you were trying to think like the masses. You were guessing a lot of assigned reading books, a lot of high school type books. And you started out and you said, okay, Ulysses and Don Quixote, which Don Quixote is already on the list. You must have missed that. But Ulysses was correct. And then you said, no, Magic Mountain. And you had six question marks after that. I'm not sure you were serious if you really thought that was going to be on there or not. You know that that's a. An underappreciated book, one of your favorites. Then you said, where's the fan notes? Which I know you've been reading recently. Frederick Exeley. I'm going to chalk that up to recency bias. And then you guessed to the Lighthouse, David Copperfield, and Brave New World. Brave New World is like one of those assigned reading kind of books. And we've already talked about Wolf and Dickens and some of the problems there. It wouldn't surprise me if Brave New World had made it onto the list. Like, it wouldn't surprise me if Of Mice and Men were on here or Animal farm or maybe 50 years ago, the Scarlet Letter probably would have been on here, because those, like I said, those are books people tend to have assigned to them. Then you guessed Paradise Lost, which was a really good choice that probably should be here, but with the bias against poetry, doesn't make it. You guessed Tales of a Fourth Grade Nothing, which I would consider it. I'd love that book. But no, that's not it. Then you said something pulpy. And then at this point I'm saying to you things like you're going to smack your forehead when you hear the answer. You guessed Tom Sawyer, which is another book that maybe is more known than respected. You guessed the Iliad, which probably should be on here. And you guessed A Christmas Carol, which is Dickens again. Then you guessed the Old lady who Swallowed a Fly. And I could tell at that point you were getting desperate, so I gave you a hint. I said, as a Francophile, you should be guessing this one. You were ready to resign as president of the Literature Supporters Club. I talked you into staying. And finally I had to tell you that the other book, along with Ulysses and the top two, is Proust, either In Search of Lost Time or Remembrance of Things Past, however you like to say the title. And then you assigned yourself an F. But I'm going to say you did Ms. Proust, but you got Ulysses right away. And I'm a generous grader, so I'm going to give you an F plus.
Mike Palindrome
I was trying to think, like the list. Yeah, I was trying to. Yeah. So I started to think of, like, well, what's missing on this list? What are some personal favorites? And also what are some irrational personal favorites. And I think had I stuck to the personal favorites, I would have come up with Proust pretty quickly.
Jack Wilson
Yeah.
Mike Palindrome
Yeah.
Jack Wilson
But, like, To Kill a mockingbird is number 17. Yeah. That's not a book that a serious critic would name that high. But when you see that it's number 17, then you think, oh, well, you know, what's. What's number one going to be? The Great Gatsby. You know, it is. Which is very high. So. Okay.
Mike Palindrome
I thought the Red Pony. Thank you.
Jack Wilson
Okay, so let's go through the list. We'll start with number. Let's do these in groups of five, and I'll read out the batch of five, and then we'll talk about the different books, the individual books in that group. So 25. The Grapes of Wrath by John Steinbeck. 24. The Odyssey by Homer. 23. Madame Bovary by Flaubert. 22. The Stranger by Camus. And 21. The Trial. What do you think of these choices being on the list of top 25?
Mike Palindrome
I mean, I think the Grapes of Wrath, there are a number of books on this list that I consider YA novels. I would pick east of Eden over Grapes of Wrath.
Jack Wilson
Yeah.
Mike Palindrome
I do think that people like to recognize books that they've read. And I don't know what percentage of this country has read Grapes of Wrath, but it must be, like, high. Very high.
Jack Wilson
Yeah.
Mike Palindrome
Maybe at least 5% has read grapes of Wrath.
Jack Wilson
Yeah. And it's got. Maybe they've read excerpts from it. It's got that famous sort of speech by Tom Joad, But I'm guessing it's just a lot of people read it when they were in junior high school or high school, and they just remember it, and they probably loved it. And it's. It's. It's a great book. It's just. It's that Patrick Ewing thing. He was a great player, but when you start talking about the other candidates, it just isn't. It just isn't going to make it into the. Into my top 25. I have a list of books that I think belong here. And. And there's maybe 10 or 12. And the grapes of Wrath is one of the first to go.
Mike Palindrome
I'd replace the Trial with Kafka Short Stories. Back to what you had said earlier.
Jack Wilson
Yeah. And Metamorphosis.
Mike Palindrome
Yeah.
Jack Wilson
I was really Surprised. That, to me, just showed that people must know the Metamorphosis and must have read it as often as the Trial. I think it really is. They're thinking, well, that can't be a great book because it's so short. But it's not that. I mean, it is a novella, but it's not. Yeah. Metamorphosis and Other Stories. And then include the Hunger Artist. That clearly could be in the top 25, but doesn't have to be the Trial.
Mike Palindrome
I did like that they included foreign novels like the Stranger and Madame Bovary, because sometimes I see a list and there isn't a single foreign novel other than War and Peace.
Jack Wilson
Yep. And the Odyssey I am including in the top 25 along. I'm going to kind of cheat, I think, and say the Iliad and the Odyssey and just say Homer. But definitely that book is so good and so important that it belongs. So I would definitely keep Madame Bovary and the Odyssey, at least out of this batch of five.
Mike Palindrome
Yeah. I keep the Stranger, too, because I think the Stranger was kind of a groundbreaking book when it first came out. And it's still red today.
Jack Wilson
Yeah. Okay, so let's look at the next five. Number 20, Adventures of Huckleberry Finn. 19 the Brothers Karamazov. 18 the Bible, 17 To Kill a Mockingbird, and 16 Lord of the Rings.
Mike Palindrome
I'd replace the Bible with Herodotus. I mean, if we're looking for varieties
Jack Wilson
of stories, well, some people are probably looking for the word of God.
Mike Palindrome
Yeah. And this grouping, other than Brothers Karamazov, to me, just really just smacks of ya.
Jack Wilson
Yeah. Huck Finn, To Kill a Mockingbird for sure. It is a great novel. I don't mean to disparage it, but in terms of just, you know, the greatest books of all time, I don't think it. I don't think it quite measures up to that. The Bible is weird to be on here because it kind of made me. It's so unusual among all these other novels that it seemed like, well, if you're gonna. I'm guessing this is just because this was an average. There's probably a lot of lists or a handful of lists that named it number one. And then it seems like you'd either have it number one or not at all. And then that somehow averaged out to number 18. But it's a little weird to say Lord of the Rings, To Kill a Mockingbird, the Bible.
Mike Palindrome
Yeah. I think the other thing that I object to in this grouping is that this is often the case with ya. Is you're reading for kind of a moral lesson and you're reading for the substance of it. Like, oh, I want to learn about trials and, you know, let me read To Kill a Mockingbird.
Jack Wilson
Yeah.
Mike Palindrome
And I want to learn about slavery. I'll read Huckleberry Finn. And so, yeah, this. And I, I struggle with this because on the one hand, you know, I want more people to read fiction, but on the other hand, it kind of drives me crazy that the standards have become so, like, democratic. Like, I mean, where's an infinite Jest on this list? But for that matter, like, where's Midnight's Children? I mean, these are, I guess, so called difficult books.
Jack Wilson
Right.
Mike Palindrome
Because the plot doesn't clang you over the head.
Jack Wilson
And the theme. Yeah, the theme, you might say, well, infinite jest, you know, what is that about really? Huck Finn is anti slavery and is about racism and To Kill a Mockingbird. Same thing. And those are just when people are. Whether it's because people are reading it or the people who are filling out the survey, you feel like, well, a great book should, should do something edifying or should change people's minds for the better.
Mike Palindrome
Yeah. I will say though, that everybody should read every book on this list. So. Yeah, that's true. That's the part of me that just wants people to read more fiction. And there's something incredible to be learned by reading the Bible.
Jack Wilson
Yeah, yeah.
Mike Palindrome
I'm talking about like just storytelling, so.
Jack Wilson
Yep.
Mike Palindrome
And the shifts of style. I mean, that's why I thought immediately of Herodotus. The focus of each of the episodes in Herodotus is, you know, really different. So it kind of challenges you to get out of your conventional modes.
Jack Wilson
So.
Mike Palindrome
Yeah. So I'll say that for this list, generally, in defense of this list.
Jack Wilson
Yeah. Oh, yeah, yeah. If you had this as your list of 25 books I'm going to read this year, you'd have a great year. I mean, you'd learn a lot and you'd have a nice mix. You could do a lot worse than this list. Okay, let's look at the top 15. So counting down 15, Wuthering Heights. Emily Bronte. Lolita is number 14. Nabokov. Number 13 is War and Peace by Leo Tolstoy. Number 12 is Pride and Prejudice. Number 11 is Crime and Punishment. Dostoevsky.
Mike Palindrome
I love this block. I think other than Wuthering Heights, which I'm a Jane Eyre person, but I have been thinking of trying Wuthering Heights again. Heathcliff and Catherine just kind of drove me crazy and I Couldn't finish the book. But I've met more people who were Wuthering Heights rather than Jane Eyre.
Jack Wilson
Yeah, Wuthering Heights. I mean, I love Jane Eyre, too. It is weird that Jane Eyre is not on this list and that this is the only book by abrante on here. But Wuthering Heights is so weird and out there and intense. And I can see where it makes a good claim for itself as being deserving on a list like this because of all of its unusual qualities. Jane Eyre is just very, very well done. And it could probably fit right in here, right in this block. I mean, Lolita. I'm not sure what to think about Lolita. I'm starting to worry about Lolita a little bit. I could see removing it from the list or moving it down, but there is something about it that is. I don't know. The jury is still out, I think, a little bit.
Mike Palindrome
Yeah, I reread it recently and the disturbing parts are incredibly disturbing.
Jack Wilson
Yeah. Yeah. And I'm not sure why do we have to have it on here. It could be a lot lower on people's lists. If you see a list and you see lolita is number 14, you almost have to read it. And maybe it could be more of a niche, more of a specialty, and hopefully people would be reading it for the right reasons. Right, okay. But, yeah, I mean, look at the books on this list. Pride and Prejudice, War and Peace. That's a really. Those are really good examples. There's probably a lot of people who would say, what? Those didn't make it into the top five. But when you hear some of the books we still have ahead of them, it's hard to crack the top five. So here we go. Number 10, Anna Karenina. Number nine, Don Quixote. Number eight, Moby Dick. Number seven, the Sound and the Fury by William Faulkner. And number six, 1984 by George Orwell. So I think we can start talking now about there's books that we maybe want to move up or books that didn't make it onto the list that we would add. Are we seeing any in this group that you think could be moved down or removed altogether?
Mike Palindrome
Yeah, you know my feelings about Don Quixote, but you would have to include
Jack Wilson
it on a list. Right. So you'd maybe add it if you were doing a list. Maybe you'd have it at number 25 or something.
Mike Palindrome
I was thinking. I was thinking a 99, but in 1984, I. Yeah, I actually think Orwell's essays or down and on in London and Paris are better books, but they're certainly, in any case, not ahead of Moby Dick and Anna Karenina.
Jack Wilson
Yeah, right. That's one where. 1984. I don't know if that made my Revised list of 25 again. I know why it's here. It's probably. It might be the most. A book affected me when I was in high school, and if I had stopped reading then, and I had gone on and become a doctor or something, and only, you know, just kind of stopped reading literature, I don't know if I'd have been a doctor. But you know what I mean? If I had just. If that had been kind of it, I might have looked back on it and said, well, if I'm filling out this survey, 1984 has got to be on there. That's one of the best books I've ever read. It is a great book. The Sound and the Fury. I just. I'm startled. I'm astonished that it's up here. Number seven, ahead of War and Peace.
Mike Palindrome
Yeah.
Jack Wilson
I just don't see it. I mean, I don't think Faulkner would have ranked it ahead of Anna Karenina.
Mike Palindrome
Yeah.
Jack Wilson
We kind of skipped past something, which is that there were only two authors who had two books on the list, and that was Tolstoy and Dostoevsky. Certainly those four books that we're talking about, Brothers Karamazov and Crime and Punishment and Anna Karenina and War and Peace, they're very deserving. But it does feel like somehow they managed to avoid what seems to have struck Homer, which is, well, you can have the Odyssey or the Iliad, but not both. Yeah.
Mike Palindrome
I mean, I think because they're so different. I think most people have read both by Dostoyevsky and both by Tolstoy if they read one. Whereas someone, like, who reads Dickens, they're just like, well, I read Bleak House, so I'm not going to read Tale of Two Cities.
Jack Wilson
Right, right. Or I wonder if Jane Eyre didn't make it because people thought, well, there's got to be a book by a Bronte on there. Yeah, or Pride and Prejudice. You know, why not Persuasion or Sense and Sensibility? It's like, well, this is my favorite of Jane Austen's book. So I'll put this on the list, and then I can move on and look at other authors and other books. So let's take a quick break, and then we'll come back with our top five, and we'll do our revisions to this list.
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Jack Wilson
Meal and Hunt Tricks Meal have just dropped at McDonald's. They're calling this a battle for the fans. What do you say to that, Rumi?
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Jack Wilson
It is an honor to share.
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Jack Wilson
It is our larger honor. No, really, stop. You can really feel the respect in this battle. Pick a meal to pick a side and participate in McDonald's while supplies last. Foreign. Okay, we're back. So, Mike, we're up to the top five. Things kind of fall apart here for me a little bit, but. Yeah, let's see. Okay, so number five, 100 Years of Solitude.
Mike Palindrome
Yeah.
Jack Wilson
Number four, the Catcher in the Rye. J.D. salinger. Number three, the Great Gatsby by F. Scott Fitzgerald. Number two is Proust and number one is Ulysses. Or we could say number two is Ulysses and number one is Proust. What do you think of the top five?
Mike Palindrome
This is the weakest batch. I mean, yeah, 100 Years of Solitude is a great book.
Jack Wilson
Yeah.
Mike Palindrome
It belongs in the top 20, I would say. But Catch and the Rye and Great Gatsby. Yeah, May maybe Great Gatsby in the top 20, but yeah, catcher in the
Jack Wilson
Rye, I'm moving that one. That. That seems like it affected people personally in such a personal way.
Mike Palindrome
Yeah.
Jack Wilson
But I don't know if it is anymore. That's the other thing. You know, if this is just if. If a lot of these lists were done in the last. Over the last 20 years, let's say. And you know, we might be moving on a little bit from the Catcher in the Rye. I don't know that people are reading it and finding it quite as meaningful as they did in the 80s and 90s.
Mike Palindrome
I mean, it's a book everybody knows. So, like I was thinking as I was going through this list, like, have you ever met someone who's read X book? It's been a Long time since I've met someone who's read Glass Bead Game or the Man Without Qualities, which I think are two fantastic books. But I find that everyone in the world knows Catcher in the Rye.
Jack Wilson
I had a friend in high school who, at the end of high school, he said, I've never read a book. He had never finished a book because he would read what he needed to read for the assignment. And we never, you know, he just. He was watching TV and doing other stuff. It just didn't. It just wasn't a thing that he could do to completion. And then he called me up when I was in college and he said, I read the Catcher in the Rye. It was awesome. You know, I loved it. And it was. There is something about that book. It's a book for people even who don't really like books or who don't. It's the one that can grip them with the style and the. And the ideas and the narrator, I think.
Mike Palindrome
Yeah, yeah. I think it was meant for a very broad audience. It was meant for adults, I think. I remember reading the Salinger was surprised that it was being taught in high school.
Jack Wilson
Yeah. Right.
Mike Palindrome
And like Great Gatsby, this goes back to my personal favorites, I think. You know, this Tender Is the Night is my favorite of Fitzgerald's.
Jack Wilson
Right, right. And if we're doing the great books and not the best known books, why not Tender Is the Night? Although there is something kind of perfect
Mike Palindrome
about Gatsby, I think it's maybe the first of its kind. There's been so many novels that have been influenced and inspired by the Great Gatsby. So. Yeah, I started thinking, I don't know if you remember this, but Deadport Society, Robin Williams's prep school teacher's character, the first day of poetry class has them open up their textbook and there's something called the Pritchard scale of a poem. I don't know if you remember this.
Jack Wilson
Yeah, yeah, yeah.
Mike Palindrome
And it ranks poems by graphing perfection on a horizontal axis against importance on a vertical axis. And he has them tear the page out and just dismiss that. And I think of this often because for people, perfection, meaning aesthetic perfection, poetic perfection. I think more and more our society is just dismissive of perfection and focused on importance.
Jack Wilson
Yeah. Well, this list is kind of a bit of a rip off the page thing. I think Wuthering Heights being here and Jane Eyre not being here is. Is choosing the unruly rather than the perfect.
Mike Palindrome
Yeah. I mean, putting Ulysses is always, you know.
Jack Wilson
Yeah. And going with the Great Gatsby at number three is kind of choosing perfection over the unruly. With Tender Is the Night probably being a stronger novel, but being harder to grapple with. It has more aesthetic imperfections. You know, it's sort of more ambitious, and it's also less contained and less orderly.
Mike Palindrome
Yeah.
Jack Wilson
Okay. So are you okay with Ulysses and Proust being 1 and 2 or 2 and 1?
Mike Palindrome
Yeah. I mean, I would always vote for the French guy.
Jack Wilson
Yeah. Okay, so let's. Let's save that discussion. Or I guess maybe that's enough. You would take Proust. You'd put that as number one and put Ulysses number two? I think I would as well. So let's not. Oh, go ahead.
Mike Palindrome
Yeah. I was going to say, ironically, I think the longer work is a more accessible book.
Jack Wilson
Yeah, yeah, it kind of is. You don't need to know as much outside of the book.
Mike Palindrome
Yeah, yeah.
Jack Wilson
You know, Ulysses, I think you. You can read it, and I'm sure there will be people who will say, well, that's not true. I read Ulysses. I loved it. You just kind of go through the passages where you don't really know what's going on. You don't need to read it with an annotated guide or anything like that. But Proust is more. He gives you his universe. He's not. You don't have to read Proust with footnotes the way you need to read Ulysses to kind of grapple with what it is that Joyce is talking about.
Mike Palindrome
Yeah. Green.
Jack Wilson
So let's talk about some absences. Why don't we just name a bunch of things that didn't make it on here before we talk about which books we would remove to make room for them? We've talked about Virginia Woolf. It's hard to believe that there is a list of top 25 books that doesn't have a book by Virginia Woolf on it. I was shocked that Middlemarch didn't make it on here. I thought given the. Given this list and people putting things like Wuthering Heights and Pride and Prejudice and Anna Karenina and Moby Dick and, you know, all these 19th century novels, and for a lot of people, Middlemarch is their favorite 19th century novel. I guess it's just too small of a group of people who ascribe that to it.
Mike Palindrome
I think it's such a glaring miss that this list can be torn up like this. This is the equivalent, and I forget what David Foster Wallace says of using a Stradivarius to hammer nails.
Jack Wilson
Okay. I would. I. You had Magic Mountain with six Question marks. I would have Boswell's Life of Johnson with six question marks. Yeah, that, you know, kind of shocking. No Henry James on here. But that is probably one where he would be dividing up his. His votes among 10 different books. I'm not sure. Portrait of a Lady, maybe.
Mike Palindrome
I would vote for Portrait of a Lady. I mean, the fact that there's no Henry James, George Eliot or Virginia Woolf, again, he just. This is very bad.
Jack Wilson
Or Charles Dickens.
Mike Palindrome
Yeah, yeah.
Jack Wilson
A couple of other huge. Mrs. Dante, Divine Comedy.
Mike Palindrome
Yeah. Well, I guess that was no poetry.
Jack Wilson
No poetry. And I guess Shakespeare, I would say even if you cheated and said Shakespeare's collected works, you could have it on here. Hamlet, you would think might have made it on as something that everybody read in high school and all that. I think people just thought, oh, that's not a book, that's a play.
Mike Palindrome
Yeah.
Jack Wilson
Chekhov's short stories. I would have for sure. There's no short stories on here. Which feels like. I mean, Chekhov would be the one. If you're going to have any.
Mike Palindrome
Right.
Jack Wilson
So did you have any others?
Mike Palindrome
I had a bunch. A Dance to the Music of Time. David Copperfield, Blood Meridian.
Jack Wilson
Oh, yeah.
Mike Palindrome
Beloved.
Jack Wilson
Oh, Beloved. Yeah, yeah, that was on my list, too. That's crazy that it's not on here.
Mike Palindrome
Yeah. Sons and lovers, catch 22. If we're gonna put in Catch her in the Rye, I mean, boy.
Jack Wilson
Yeah. So the Scarlet Letter, I mentioned, there's no T.S. eliot. I thought maybe the Wasteland would get on here, I guess. No poetry. And then there's a whole bunch. If you think a little bit. Once you get out of the framework of this list, you think of other countries and you have. I mean, if you have the Bible, if you have the top 25 books of all time, you could have the Quran, you could have the Art of War, you could have the Upanishads. You could have the I Ching, Herodotus, you mentioned Thucydides could be on here. The Dream of the Red Chamber, you know, there's. There's tons. Basho's Haiku, I would want on here. Frankenstein.
Mike Palindrome
Oh, yeah.
Jack Wilson
You know, and then there were a few. I was kind of surprised. I was surprised. Given the list, I was surprised on the Road wasn't on here. Or maybe Les Miserables. You know, there's books that kind of. Everybody knows or thinks of as being big and important. A lot of people love the Count of Monte Cristo. I've seen that mentioned in a lot of stuff lately. Baudelaire would be kind of A good choice to make it on here. So there's a lot that we'd have to get rid of, though. So did you make a list of the ones you would cross off to make room for all these others that we've just mentioned?
Mike Palindrome
Yeah, I mean, I probably cross off Catch on the Rye, 1984. Yeah.
Jack Wilson
To kill a Mockingbird, To Kill a
Mike Palindrome
Mockingbird, Lord of the Rings, the Bible, Huck Finn, Grapes of Wrath, the Trial, maybe even the Stranger. I'll say these lists don't annoy me as much as they used to because I think I've just seen so many of them.
Jack Wilson
Yeah, right.
Mike Palindrome
Sometimes I'm pleasantly surprised. Like, I'll see a list that has Berlin stories by Christopher, or if you would like, a top 100.
Jack Wilson
Yeah. Or a list that's made by, like, an author or a critic for the BBC or something. And then it's kind of. Then you get a little more idiosyncratic. And, you know, it kind of reminds me, I used to look at lists that would rank Beatles songs, and you look at a couple and you see someone chose Revolution number nine and in the. You know, as number two or something, and you think, oh, come on, how could you? You know, you've. You've got that ahead of hey Jude and Yesterday, you know. But then when you read. After you've read 50 lists like that, you're kind of glad that somebody did put it as number two and made the case for that and said this was. This was really something to put this on a. A big album by a group, you know, the most popular band of its day of all time, really. But, you know, they were the number one band in the world, and they put something totally experimental on their album, and that was a big deal that. That changed the way people thought about music and. And thought about pop groups and what you could. What you could get away with. And it opened people's minds to possibilities and all of that. So it's kind of like, oh, okay, that's. You make the case for it. But I wouldn't want to be stuck with only one list where Revolution number nine was number two. And I was trying to hand somebody a list of. Here's the Beatles songs you should listen to if you haven't heard them before. Right.
Mike Palindrome
I did like that. Everybody on the list is dead. Yeah, that was good.
Jack Wilson
Yeah. There is a real bias toward the 19th century. I think, even now, if you redid this in 20 years, and every list was something that had been done from now until 2046. Beloved would be on here for sure. And probably the Grapes of Wrath and things like that would just fall out naturally because they're too black and white. We're moving too far ahead of them. So anything else? Maybe we've covered this. I feel like. I feel like we did a pretty good job. Oh, I did make a new list. Yeah. Yeah. Because I was trying to make sure, you know. You want me to read it?
Cass Sunstein
Sure.
Jack Wilson
Okay, so my new list. Number one, Shakespeare's Collected Works. A bit of a Cheat. Number two, Proust. Number three, Dante. Four, Homer five, The Bible six. Plato's Republic and Other Dialogues. I thought we'd just include all of plato, I guess. 7. Paradise Lost 8. Ulysses, James Joyce. 9. Moby Dick 10. Aristotle. Just include all his collected works on there. 11. Don Quixote 12. War and Peace 13. Chekhov Short stories. 14. Anna Karenina 15. Middlemarch 16. Boswell's Life of Johnson 17. Pride and Prejudice 18. Madame Bovary 19. 100 Years of Solitude 20. The Brothers Karamazov 21, Beloved 22. Crime and Punishment 23. The Scarlet Letter 24. Huck Finn 25. Wuthering Heights. And then I've got 26 through 30 is Virginia Woolf, Henry James, Dickens, the Great Gatsby and the Lord of the Rings.
Mike Palindrome
Yeah, I like it better.
Jack Wilson
Right. I could have snuck the Magic Mountain on there just to get your. To get a more. A bigger thumbs up from you.
Mike Palindrome
I think it'd be interesting if they would say whatever they base their lists on. It showed the average age when someone read something because I think for you and me, we're voracious readers. So by the time we're in our 30s, we've read all these which makes it kind of a. Safer picks than to put books that people don't like. I, I doubt anyone's read A Dance to the Music of time in their 20s.
Jack Wilson
Yeah, right.
Mike Palindrome
You know, or you know, the Magic Mountain. It's unusual. You know, it's. I think there is something about trying to capture people. It's the whole like parent. All parents want their kids to read fiction, but when they, when the parent, the parents themselves don't. And they don't many of them and they don't set a good example. And this idea that all you need to do is read fiction up until you graduate college. Lists like this sometimes remind me of that. Like they don't want to put books on here that adults have to have read will more likely have read in their 40s and 50s.
Jack Wilson
Well, who do you think would be let's say you had to choose. Instead of choosing a book or an author, you were choosing a person to make a list. Who do you think you would choose first, all else being equal? A 30 year old or a 60 year old?
Mike Palindrome
Oh, I mean, I would, I would always choose the older person.
Jack Wilson
Just figuring they've read more and they've had more time to process and absorb and rank.
Mike Palindrome
Yeah. And, you know, I wouldn't mind getting somebody who is a combination of pretentious and arrogant.
Jack Wilson
Yeah, yeah.
Mike Palindrome
Like those Criterion lists where they ask like Lars von Trier to pick his 10 favorite movies and they're none of you. We've never heard of any of them.
Jack Wilson
Right.
Mike Palindrome
And I kind of enjoy that, you know.
Jack Wilson
Yeah, I kind of do too. And I kind of feel like if you're too nice and too democratic and not opinionated enough, you end up choosing a lot of books because you think it's almost like you're. It's almost like you're a high school teacher planning a course guide and knowing, well, if I pick too many things that are too difficult to read, I'm going to lose my students, I'm going to lose the class. So I've got to pick things that people are going to like to read and that they'll get something good out of it. So you end up with a book like Huck Finn and the Catcher in the Rye and you'd have, you know, like it was. I wasn't, when I was talking about the books that were on the list from 25 to 3, I wasn't going to come in there and rail against To Kill a Mockingbird. And I wanted to give it credit for doing what it did. It's like a. It'd be like a movie like the Titanic or something like that where it's like, well, it's a great popcorn movie and it put people into the theater. Maybe it's not a good comparison because Titanic was kind of sheer entertainment and To Kill a Mockingbird has a really strong social message, but you know what I mean? It kind of felt like, well, this. Okay, good for. Good for To Kill a Mockingbird. I'm glad it made this list of top 25. Same with the Grapes of Wrath. Good for John Steinbeck. We kind of trashed him in our John Steinbeck episode. But I'm good for him. I'm glad this book is doing well and made it into the top 25.
Mike Palindrome
Maybe we should make lists that, you know how these things online on Substack, it tells you this is a six minute read. Maybe we should make a list. The top 25 books you can read in a week.
Jack Wilson
Yeah.
Mike Palindrome
Top 25 books you can read in a month. The top 25 books you can read in a year.
Jack Wilson
Yeah.
Mike Palindrome
It'll take you a year.
Jack Wilson
I've noticed that in the Criterion. I just subscribed to the Criterion Channel and I've noticed, you know, they'll have categories and they'll say things like the, you know, in January, they have the Fresh Starts collection. And that was. Had Sleepless in Seattle in it and Lost in America. And you're sort of, I think, thinking, oh, new Year, I'll have a fresh start. And there'll be a movie in that theme. Or they have the Julianne Moore collection and it's movies that Julianne Moore is in. And then they'll have, you know, and then all the. The big ones, French New Wave and stuff like that. And then they'll have. They have categories like under two hours, under 90 minutes, under 60 minutes, under 30 minutes. And you just think you're trying to catch people who say, got about an hour to devote to cinema today. Or, I'm getting a little tired. I'll just put on something that's 30 minutes. And it's very helpful. And. Yeah, I think we could probably do that. You know, this is. Maybe we could get more granular and say, like, this is. Here's a list of 5 books you could read on the train, on your commute. And, you know, we probably wouldn't have. I don't know, we probably wouldn't have Proust on there or Ulysses, but maybe we'd have Chekhov.
Mike Palindrome
Yeah. I mean, you can read Waiting for Gato in one sitting, you know.
Jack Wilson
Yeah.
Mike Palindrome
That would be probably like my number one. One sitting book. Can't get up until you finish it. Yeah. Or, you know, Cherry Orchard. Like, you know, you can read Cherry Orchard in one setting.
Jack Wilson
Yeah. Or the Metamorphosis.
Mike Palindrome
Yeah.
Jack Wilson
The possibilities here are endless. Okay. Well, anything else? Before we sign off here, we should
Mike Palindrome
do a list of books by people under, you know, 40. I think that, you know, those 40. Under 40. I always curious how those age. You look back and you're like, a bunch of these people. Really didn't produce much after 40. After 40, right.
Jack Wilson
Yeah. Yeah. I think it would be. I think our. I think most of these books would be by people who were under the age of 40.
Mike Palindrome
Yeah, that's true.
Jack Wilson
Right. I mean, it's. It's there. It's kind of a young man's game to write great books. Apparently.
Mike Palindrome
Yeah,
Jack Wilson
that would be an interesting thing to check out. One thing I didn't look at my list of 30 or 25 that I made here is how many were by women. I think at least 5, which is pretty good given. Ideally, it would be at least half, but given that we're talking about whole centuries of where women were not allowed to be educated or be author. You know, like, I've got Shakespeare and Homer and the Bible and Dante, and they're just going to tilt things toward the men just because of history. So I did the best I could. The other thing is, we didn't even mention this, but it's a huge anglophone bias to this list. I'm sure if we were two people who were in China or Japan or something, we would have a completely different take on which of these books would make it into the top 25.
Mike Palindrome
Right.
Jack Wilson
Oh, Borges. We didn't mention him.
Mike Palindrome
Oh, yeah, yeah.
Jack Wilson
I was just thinking if we were in South America, we'd probably have a whole different list, too.
Mike Palindrome
You know, be a good list. Is list Top 25 favorite books by writers, because I think we both have a sense, like, Borges would be easily in the top 10.
Jack Wilson
Yeah. Or you mean like writers favorites.
Mike Palindrome
Yeah, yeah, yeah, yeah, yeah.
Jack Wilson
Right.
Mike Palindrome
I mean, Proust might be number one on that list, too.
Jack Wilson
Yeah. Yeah, it might be. I wonder if Ulysses would drop.
Mike Palindrome
Probably Ulysses would definitely drop. I think books like Lord of the Rings and To Kill a Mockingbird wouldn't have a sniff of the top 100.
Jack Wilson
Well, it depends on which writers you're asking. If you include genre writers, Lord of the Rings is probably going to do really well. That's like such an OG. And if you include romance writers, Pride and Prejudice is probably going to be in the top three.
Mike Palindrome
Yeah, no, I will put that in the top 20.
Jack Wilson
Yeah.
Mike Palindrome
You know.
Jack Wilson
Yep. Yeah, it was 17 on my list.
Cass Sunstein
Yeah.
Jack Wilson
Okay. Well, this was fun. And now I am. My batteries are recharged. I can't wait to figure out what I'm going to do for Ulysses and what I'm going to do for Proust in honor of those two books finishing in the top two of our list of the greatest books of all time. And it was very fun to talk to you about the problems with the list and the possibilities for making a new and better list. Mike, as always, thank you for joining me on the history of literature.
Mike Palindrome
Thanks, Jack.
Jack Wilson
And finally today, Cass Sunstein was here to discuss how to become famous. After he and I talked about. About that, I asked him to choose a book that would be important to him. So important that he would select it as the last book he would ever read. Would he take one from our top 25 list? I think I've already told you that he didn't. Lots of other guests have done so I'm used to hearing that. I'm used to hearing those in the top 25. But he had an interesting choice and he chose it with no hesitation. Lets listen. Okay. We're joined now by Cass Sunstein, professor of law and author of the book how to Become Famous Lost Einstein's Forgotten Superstars and How the Beatles came to be Cas. This question comes from a listener who asks, what do you want your last book to be? This will be the last book you will ever read. You can either choose one that exists or describe one that has not yet been written.
Cass Sunstein
It's Possession by As Byatt, which is my favorite novel ever and I've read it six times but I'd love to read it a seventh time. It has all the world in it, heightened the best romance you could imagine. A lot about aspirations and connections and missed connections and reconnections and what matters most in human life.
Jack Wilson
Yeah, that's a great choice. I feel a lot of people who have answered the question have chosen things either from their childhood or kind of when they were first coming of age. But I'm guessing that book must have come out when you were maybe in almost mid career. Did it feel like it was the book you had been waiting for?
Cass Sunstein
Well, I'd say it hit me like a time of bricks in the best way.
Jack Wilson
Yeah.
Cass Sunstein
I read it in a. In a fever. Possession creates a fever, I think for those who are receptive to it. And I think something the Time Traveler's Wife is more like a book I was waiting for. And I really love it. I'm thrilled by its existence. Forgive me, Andrew Niffenberger, your book is fantastic, but Possession is the one I choose deeper.
Jack Wilson
Right. Okay. Well, we talked about fame when you were here before and it feels to me like that's a book that could use a bit of revivifying. It doesn't get talked about nearly as much as it did in the first five or ten years after it came out.
Cass Sunstein
Yes, I think that biat's Possession is better than anything written by Joyce or Dickens. And I dearly love Joyce and Dickens.
Jack Wilson
Well, we did talk about the importance of having a champion and so maybe that will be maybe this when this comes out, it'll be the first step in our re championing of as by its possession.
Cass Sunstein
That would be an honor.
Jack Wilson
Okay, Cass Sunstein, thank you so much for joining me on the history of literature.
Cass Sunstein
Thank you. Great pleasure.
Jack Wilson
Okay, that's going to do it for this episode. I'm thankful to Cass Sunstein and to Mike Palindrome, both University of Chicago folks, and to Harper Library. Do you see how proud you should be of your alumnus Jack Wilson? Who else can take something as intelligent as Gore Vidal talking about T.S. eliot and Henry James and turn it into a discussion of Three's Company? Oh, man, what can I say? Maybe it's that theme song. Come and knock on our door. What an earworm. And what a nice sentiment. Come and knock on our door. Yes, we've been waiting for you. That show must be the most California show ever. That apartment, that condo that they were living in. Although Chips California Highway Patrol was pretty California too. Oh, I tell you what, people, the 80s are my era. You know that. But the 70s were a pretty great time to be alive, too. I'm Jack Wilson. Thank you for listening and we'll see you next time.
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Date: April 2, 2026
Host: Jacke Wilson
Guests: Mike Palindrome, Cass Sunstein
In this episode, Jacke Wilson tackles the ever-controversial task of listing "The 25 Greatest Books of All Time." Joined by Mike Palindrome, president of the Literature Supporters Club, Jacke scrutinizes the process of creating such a list, the inherent subjectivity behind it, and its cultural significance. The conversation is a lively, critical—and frequently humorous—exploration of what makes a book “great.” The episode concludes with guest Cass Sunstein sharing his personal "last book" pick, diverging from the lists entirely in a moving, original way.
Jacke introduces the episode’s theme: Investigating the "25 Greatest Books of All Time." Rather than just picking his personal favorites, Jacke decided to use an aggregate list sourced from over 100 prominent literary rankings (BBC, Penguin, various reader surveys, etc.).
The T.S. Eliot/Henry James/Gore Vidal Anecdote (05:35–15:00)
Jacke and Mike on the Ubiquity of Lists: (e.g., college rankings, sports) and whether they offer comfort or shut down critical thinking.
Mike: "Lists... allow us not to think and feel justified in not thinking and make us feel comfortable with a kind of false sense of definition." (19:14)
Paradox: Lists are both intellectually lazy and, for the “sports-obsessed side of me,” perversely satisfying (20:29).
Flaws in Book Lists:
Mike: Notes positive inclusion of foreign novels (e.g., Madame Bovary, The Stranger) compared to some lists.
Discussion:
Discussion:
Discussion:
Discussion:
Discussion:
On the Function of Lists:
"I think that lists...allow us not to think and feel justified in not thinking." – Mike (19:15)
On List Fatigue:
“These lists don’t annoy me as much as they used to because I think I’ve just seen so many of them.” – Mike (57:01)
On What Makes a Book ‘Great’:
“You have to choose the right things to read—which is where a list of the 25 greatest books of all time comes in... But I'll tell you this: they are great books, each and every one. There are no skips on this list.” – Jacke (15:12)
On Ulysses vs. Proust:
“The longer work is a more accessible book. You don’t need to know as much outside of the book.” – Mike (51:23)
On Literary Democracy:
“This drives me crazy that the standards have become so, like, democratic...where’s an Infinite Jest on this list?” – Mike (36:15)
On High School Canonization:
“To Kill a Mockingbird... That’s not a book that a serious critic would name that high.” – Jacke (30:50)
This engaging, opinionated episode is a master class in how subjective, debatable—and necessary—literary lists are to spur conversation and re-examination of the "canon." Jacke and Mike’s rapport is sharp and funny, questioning why some books persist at the top and others are perennially overlooked. The inclusion of Sunstein’s very personal “last book” reminds us that no ranking can wholly capture what books mean to individuals.
Summary prepared by: [Your Podcast Summarizer Bot]
For listeners who want the wit, deep-dive, and surprises of Jacke and his guests—with a healthy dash of debate and literary inside jokes, this episode delivers.