Jordan Klepper's Reading List (From Ryan Holiday)

After their conversation for The Daily Stoic Podcast, Ryan gave Jordan Klepper, comedian, writer, and correspondent on The Daily Show, a few book recommendations at The Painted Porch. Follow Jordan on Instagram @JordanKlepper and check out his upcoming live show dates on his website https://www.officialjordanklepper.com/📚 Books Mentioned:Buckley: The Life and the Revolution That Changed AmericaLetter to the FatherA Marriage at Sea: A True Story of Love, Obsession, and ShipwreckDead Wake: The Last Crossing of the LusitaniaI Survived the Hindenburg Disaster, 1937How to Be Perfect: The Correct Answer to Every Moral QuestionMontaigneThe Plague: A new translationOutdoor Kids in an Inside WorldMoby-DickIn the Heart of the Sea: The Tragedy of the Whaleship Essex🎥 Watch Jordan Klepper's full episode on The Daily Stoic Podcast: https://www.youtube.com/watch?v=utF8yGyWpEgSPECIAL OFFER exclusively for podcast listeners 👉 Go to dailystoic.com/spring and enter code DSPOD20 at checkout to get 20% off the Spring Forward Challenge! Challenge yourself to spring forward and become the person you aspire to be. The Spring Forward Challenge starts March 20, 2026. 🎙️ Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and Facebook 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:14Ryan Holiday?

  You would not think that a thousand-page biography of William Buckley would be... Were you fucking with me? You're fucking with us, a thousand pages? It's incredible. Really? Incredible. Yeah? Yes. Like, first off, just because it's like this arc of history that's fascinating, and he, all these different, like James Baldwin's in there. He, I mean, he was the first person to publish Joan Didion. Is that right? Yes, he wrote for the National Review. But, yeah, so it's this arc of American history that is fascinating. So basically, he fondly recounts, he was not invited, but his brothers, at the direction of their father, go burn a cross on somebody's lawn.

• 0:56Ryan Holiday?

  Like, his father's profoundly anti-Semitic, family racist, just a reactionary bigot. And then, so when you understand that, then when you understand, when you understand William Buckley, you're like, oh, he's, he's actually doing this thing that's kind of endemic to the conservative movement, which is like, people have these opinions, these instincts. How do we intellectualize that? It's a way of creating like an intellectual cover for these sort of like primal, like emotional prejudiced ideas. Like, so there's the arc of that in his life. And then, he starts by writing a book

• 1:38Ryan Holiday?

  about liberal overreach on college campuses that his dad pays for. Is that right? Yeah. His dad was like an oil speculator. Okay. Then he is a speechwriter and advisor to McCarthy. And then next, he is this sort of Machiavellian genius behind, like, all these pivotal moments. It's fascinating. Really? You will realize that, oh, if you just change a couple of these names, it's the same things happening again. Yeah. But, but like, I, I think the Free Press, which I like for some stuff, is a similar role, where it's like, part of what it does, though, is...

• 2:24Ryan Holiday?

  Is create kind of intellectual cover for things that people want to believe. Like realizing that like, we tend to think of propaganda and misinformation as like inserting false ideas. And actually, its job is to give you reasons to believe what you already believe.

• 2:44Speaker 01

  Yes, give you, give you a way to not look like an asshole in conversation.

• 2:47Ryan Holiday?

  Yes, yes. And kind of gives you this, it's like, okay, so the Wall Street Journal is this part of the hierarchy. And then all the way down to like, you know, Charlie Kirk was in there somewhere. And then the Gateway Pundit is down here, but they're all doing this thing and they have various levels of funding. And it was, it was interesting to me to watch like how people sought him out, just like Charlie, like Charlie Kirk is this average kid who wants to go to college and some billionaires like, you're good at this, let me pay you to do that thing. And this basically is the same thing that happened to Buckley.

• 3:18Speaker 01

  Really?

• 3:18Ryan Holiday?

  And then I'd experienced that with, when my stuff started to get popular.

• 3:22Speaker 01

  Yeah.

• 3:22Ryan Holiday?

  I would get invited to these conferences and I could see they were, they were like evaluating me to be like, do you ever need anything?

• 3:32Speaker 01

  Like.

• 3:32Ryan Holiday?

  How could we get this out to more people? There's a, which the left doesn't have, it tends to be, I think, more organic. But this process of like, oh, um, this person has a way with audiences and they're fellow travelers with what we're saying. How do we bring them into the ecosystem?

• 3:51Speaker 01

  I mean, that's like, I feel like Peterson's an interesting example. Is that right? With those early Peterson, like, oh, I get this. That's a lot of sense.

• 3:58Ryan Holiday?

  I met him at some of those conferences. I met him at an entrepreneur conference and then the next thing I saw him was at a Coke thing.

• 4:04Speaker 01

  Yeah.

• 4:04Ryan Holiday?

  You know? And it's a process. Yeah, you gotta read this. Oh my God. It's, you're gonna, you gotta read every page.

• 4:11Speaker 01

  I come down to Texas and I lead with a thousand page biography on William F. Buckley.

• 4:15Ryan Holiday?

  It might be an audio book for you then, but I'll show you my office in a second. You'll see how the notes factor comes.

• 4:21Speaker 01

  I haven't even finished a Gore Vidal book, if I'm being totally honest.

• 4:24Ryan Holiday?

  I don't know if I do that.

• 4:26Speaker 01

  This is great.

• 4:27Ryan Holiday?

  Is there anything you've been reading?

• 4:28Speaker 01

  What have I been reading? So I've been. I just actually picked up the Pinchon book on the way here. So I've been reading that.

• 4:34Ryan Holiday?

  Okay.

• 4:34Speaker 01

  I have been, I picked up some writings by Camus. I like, I like me that myth of Sisyphus.

• 4:39Ryan Holiday?

  Have you read The Plague?

• 4:40Speaker 01

  Yes.

• 4:41Ryan Holiday?

  I just reread The Plague and it's another one where you're like, oh, this is, explains everything.

• 4:47Speaker 01

  Oh, that, yeah.

• 4:48Ryan Holiday?

  I have this sort of theory about like dark energy, that there's this dark energy in humanity and it goes from issue to issue, era to era.

• 4:56Speaker 01

  Yeah.

• 4:56Ryan Holiday?

  And that you realize like, oh, it's not about the plague at all. Plague is about dark energy.

• 5:00Speaker 01

  Yeah.

• 5:01Ryan Holiday?

  Cause the plague is about Nazism.

• 5:02Speaker 01

  Yes.

• 5:02Ryan Holiday?

  Uh, as a metaphor, but he's at the end, he's like, the plague just goes on to the next thing. We think we beat it, but we didn't. It just goes to the next thing.

• 5:10Speaker 01

  I think Camus was a fun one to read right now.

• 5:12Ryan Holiday?

  Yeah.

• 5:13Speaker 01

  I feel like that, that absurdist point of view feels, feels good. I was also reading Kafka because of that.

• 5:17Ryan Holiday?

  Ooh, uh, did I give you, did I give you this Kafka parenting book?

• 5:21Speaker 01

  Nope.

• 5:22Ryan Holiday?

  Cause I remember I gave you some parent, you just had.

• 5:25Speaker 01

  Yes, just had it and you gave me the self, uh, what is it?

• 5:28Ryan Holiday?

  Self-driven child?

• 5:29Speaker 01

  And this was great.

• 5:30Ryan Holiday?

  Did you like that?

• 5:31Speaker 01

  You gave me these two. Both of these are great.

• 5:32Ryan Holiday?

  Okay.

• 5:33Speaker 01

  This makes me wanna.

• 5:34Ryan Holiday?

  After a kid is in an inside world?

• 5:35Speaker 01

  Yes, it makes, this is helpful for New York.

• 5:37Ryan Holiday?

  Okay. Oh yeah, sure. Um, okay. This is Kafka wrote this.

• 5:42Speaker 01

  Oh my gosh, I read about this letter. I read about this and it's brutal, right? It's like a brutal.

• 5:46Ryan Holiday?

  Super brutal. His father was kind of like William of Buckley's father, which is like one of those overbearing, powerful people and you can sort of go two ways, you know, and he, he sort of goes in the other direction. And then he writes this letter sort of dumping out all his feelings about it. It's beautiful and haunting.

• 6:04Speaker 01

  He is lovely. And I feel like his short stories now, where things feel like they don't make sense in some ways. He taps into that in such a nice way.

• 6:13Ryan Holiday?

  Yeah.

• 6:24Ryan Holiday?

  I have many shipwrecked books for you.

• 6:26Speaker 01

  Is that right?

• 6:26Ryan Holiday?

  So this one just came out. It's called The Marriage at Sea.

• 6:28Speaker 01

  What is this?

• 6:29Ryan Holiday?

  This couple is sailing from England to New Zealand.

• 6:32Speaker 01

  Uh huh.

• 6:33Ryan Holiday?

  And in real life, a whale breaks their sailboat apart.

• 6:37Speaker 01

  That's my shit.

• 6:37Ryan Holiday?

  And they spend like, uh, three months in a raft and it's, it's like about their marriage. It's a husband and wife just stuck in this raft. It's crazy. At one time they're in the Pacific. So it's like full of light. At one time they, they catch a giant sea turtle and they tie a rope to it and they, they try to like harness it, like to see if it can pull them.

• 6:54Speaker 01

  Yeah.

• 6:56Ryan Holiday?

  But it's amazing.

• 6:58Speaker 01

  This is.

• 6:58Ryan Holiday?

  That one's good.

• 6:59Speaker 01

  I got obsessed with Moby Dick. That's probably my favorite.

• 7:02Ryan Holiday?

  Okay, well, have you written The Heart of the Sea?

• 7:03Speaker 01

  Yes.

• 7:03Ryan Holiday?

  Okay.

• 7:04Speaker 01

  Amazing.

• 7:04Ryan Holiday?

  Uh, that's one of the all time greats.

• 7:06Speaker 01

  I called the Melville Estate and they let me write at his desk for a couple of days.

• 7:10Ryan Holiday?

  What?

• 7:10Speaker 01

  A pilot, yeah. Pilot didn't go anywhere.

• 7:12Ryan Holiday?

  You were writing a pilot about?

• 7:13Speaker 01

  I was writing a pilot and I needed to get away from home. And I was like, I just need to go, I want to go up to the Berkshires. And I called him, I'm kind of a lark. I was like, you know what? I know you do some writer stuff here and there. I was like, hey, hoping they're like a Daily Show fan.

• 7:26Ryan Holiday?

  Was there any good energy in the?

• 7:27Speaker 01

  Great energy. I think, but you know, if I'm being totally honest, the energy is I didn't dare look at my phone for a second in that room. Like, I felt so guilty not being productive. I was productive for two straight days.

• 7:39Ryan Holiday?

  Interesting. Uh, this Walter Lord has a book about the Titanic that's amazing.

• 7:44Speaker 01

  Oh, really?

• 7:45Ryan Holiday?

  But then Eric Larson has one about the sinking of the Lusitania. Which, which one is more your style?

• 7:50Speaker 01

  Oh, wait, the sinking of the, oh, wait, what is that? I don't know the Lusitania.

• 7:53Ryan Holiday?

  Lusitania is the sinking of the American ship that basically brings us into World War I.

• 7:59Speaker 01

  Give me that one.

• 8:00Ryan Holiday?

  All right, I'm wearing this hat. Down it.

• 8:03Ryan Holiday?

  Dead weight.

• 8:04Speaker 01

  Look at this.

• 8:04Ryan Holiday?

  I gave Vista at Helms when he was here. This is about zeppelins.

• 8:08Speaker 01

  What zeppelin?

• 8:11Ryan Holiday?

  Which, which is, in retrospect, the dumbest idea that humans have ever had.

• 8:16Speaker 01

  I think so, right? But, but a fun idea? I mean, I imagine this.

• 8:19Ryan Holiday?

  But they kept cra- it's, I described this book as the definition of the triumph of hope over experience. Cause they would just, every single one horrendously crashed because it is a balloon filled with highly flammable gas. Powered by an engine.

• 8:44Ryan Holiday?

  This, this one, like, this is the, the famous British one.

• 8:46Speaker 01

  Yeah.

• 8:47Ryan Holiday?

  It had a smoking room inside the zeppelin.

• 8:50Speaker 01

  Amazing.

• 8:51Ryan Holiday?

  That again.

• 8:54Ryan Holiday?

  Men, people were lighting lighters and matches.

• 8:59Speaker 01

  They brought on a fire eater every time to come in. What I love is like the Gipper State Building has the the dock point. Yeah. And they're like, oh, one stop there.

• 9:08Ryan Holiday?

  Well, so the crazy thing about, they talk about this in the book. So like, okay, so you tie up a balloon to this pointy needle. All right. Um, okay. What happens when it gets windy as it often does?

• 9:22Speaker 01

  Yeah.

• 9:23Ryan Holiday?

  It, no amount of ropes are gonna secure this giant balloon.

• 9:27Speaker 01

  Yeah.

• 9:28Ryan Holiday?

  And then the people are in it, like, or whatever. It's still, whatever. So it was just the dumbest fucking idea you could possibly.

• 9:34Speaker 01

  The idea of a, like, how long was that?

• 9:37Ryan Holiday?

  Like forty years. Like it

• 9:39Speaker 01

  Really?

• 9:39Ryan Holiday?

  It lasted a lot longer than you would think it would.

• 9:45Ryan Holiday?

  It's incredible. Uh, cause he, he wrote a book about snafus, like about

• 9:49Speaker 01

  Oh, yeah, I read his book. Yeah.

• 9:51Ryan Holiday?

  Stupid things he would have done. That struck me as like just the definition of human stupidity. It's incredible.

• 9:57Speaker 01

  Give me a philosophy thing. I'm liking it. Uh, Byung Chul Han, are you reading his stuff?

• 10:01Ryan Holiday?

  No. I don't even know what you just said.

• 10:04Speaker 01

  Okay. Korean, German, does a lot of like tech philosophy right now.

• 10:08Ryan Holiday?

  Ah, Michael Scher wrote a book about moral philosophy. Did you read that?

• 10:12Speaker 01

  No.

• 10:12Ryan Holiday?

  Good.

• 10:12Speaker 01

  Really good. I bet.

• 10:13Ryan Holiday?

  It's awesome.

• 10:14Speaker 01

  Very good. I feel like, yeah, funny guy writing a smart book like this is gonna make me so jealous.

• 10:18Ryan Holiday?

  Yeah.

• 10:20Speaker 01

  I bet that book's fucking great.

• 10:22Ryan Holiday?

  It's really, it's really good. It's, it's funny and good.

• 10:26Speaker 01

  These prints are so nice.

• 10:27Ryan Holiday?

  Oh, I love this little series. And then we'll do this, um, Montaigne book that I've been reading about. He's talking about

• 10:33Speaker 01

  Zwick, wait, Zwick, I wrote, he's

• 10:35Ryan Holiday?

  The World of Yesterday.

• 10:35Speaker 01

  Yes.

• 10:36Ryan Holiday?

  So he's like the most famous novelist in Europe.

• 10:39Speaker 01

  Yeah.

• 10:39Ryan Holiday?

  Chased out of Germany the second time.

• 10:41Speaker 01

  Yes.

• 10:41Ryan Holiday?

  And then he ends up in, in Brazil, I think Brazil, and he rediscovers Montaigne, the, the French singer. And then he realizes, oh, Montaigne is writing in the middle of the religious wars of the 16th century. So it's like, he's not just exploring philosophy for its own sake. He's turning inward because the world is tearing itself apart. He's saying that the hardest To do is to to remain human in inhuman times. Montaigne was all about intellectual humility in a time when they're burning people alive for being heretics. And so how do you? How do you maintain intellectual humility when it's not just out of style? Yeah. But the opposite is the case. Wow.

• 11:26Ryan Holiday?

  It's amazing. Wow. So good. Wait, because Zwig was like a 50s writer, right? No, no, no. He was popular during the First World War. So first half of the 20th century. So this was. He wrote a bunch of novels, which are not that popular. And then he wrote a couple of biographies. Yeah, Wes Anderson loosely based one of his movies. I didn't know that. Because blast one. But The World of Yesterday is a beautiful. Is it? Yeah. And haunting, but this is, he would do these little biographies. Like he wrote a really good biography of Marie Antoinette. That's good. Right. We have one of Magellan that he wrote. Really? But the Montaigne one is his best one. Oh, I love that.

• 12:07Ryan Holiday?

  Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please spread the word. Tell people about it. And this isn't to sell anything. I just wanted to say thank you.