The Year of Pynchon feat. Devin O’Shea (Premium E290)
Devin O'Shea guides us into the world of acclaimed novelist Thomas Pynchon, whose cryptic, sprawling narratives echo the chaotic info deluge of contemporary digital culture. With Paul Thomas Anderson's newest Pynchon adaptation, One Battle After Another, hitting theaters in September 2025, and Pynchon himself releasing a fresh novel, Shadow Ticket, in October, it’s time to unpack what makes Pynchon uniquely relevant today.
From the hippie noir mystery of Inherent Vice to the critically-panned Vineland, we explore why this reclusive author has captivated (and frequently frustrated) readers for decades. Along the way, we discuss the complex relationship his work has with history, conspiracy, technology, and power.
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Comments (111)
I really enjoyed this and it made me wish I was better at reading. I've never managed to take Pynchon but I will try and I might also watch Under the Silver Lake again which now feels like it has Pynchon elements. Thanks.
We need a Philip K Dick picks episode.
The same thing happened when Pavement came out with Wowie Zowie...
Jake said “the same thing happened when…” and I instantly knew a Weezer reference was coming.
Great to hear the great folk musician Richard Fariña mentioned. Worth checking out his song Children of Darkness (also surprised that your guest didn't mention that Richard was also Joan Baez's brother in law; married to Mimi Farina nee Baez. https://www.youtube.com/watch?v=bZDLNUoliyU
This episode was really cool and interesting! As a guy from Chile, I've never been able to go through Pynchon's style. Big fan of mccarthy, Faulkner and the likes, but Pynchon feels a little to "gringo" and hard to figure out. I'll give it another chance after this episode
even as a gringo, i found pynchon too much. i will try to get into his work again tho
I've watched Inherent Vice three times. Each time I got really baked during viewing, by the end of the film I was Joaquin Phoenix, like him, I was also really, really, confused. Every time I forgot all of the film, but felt that it was a good film, so I watched it again and it happened again. I will do it again.
LOTION multinational corporation mentioned
Live Agar
Extremely deep dive!! Great episode!!!
If you liked the Greek Mythology and like musicals, check out Hades Town.
Seconded. Just recently saw it and it was amazing!
Great Ep. I'd like to follow up with the audio essay Devon mentioned but i can't seem to scrub to it. Anyone remember the name?
It’s the podcast Death is Just Around the Corner, hosted by Michael Judge. He has several Pynchon episodes, including a great series on Gravity’s Rainbow. I think the ep mentioned here was called Thomas Pynchon and the American Reconquista.
The gnosticism mention in this episode reminds me: for a future episode, I hope you find someone to tell you about the ridiculously numerous and deep references to gnosticism, esotericism, and literature in Genshin Impact. You might need to find an additional person who can explain the Chinese mythology, philosophy, and literary references.
Loved this episode. Great deep dive!
Great ep. Also true: the pronunciation of Eurydice here has destroyed me psychically.
Wtf is this? This guy is boring
I hate to be that guy, but German southwest Africa is actually today Namibia, and the genocide was committed against the Herero and the Damara/Nama peoples. The reason people began to talk about it in the 90s was due to the finding of photographs from Shark Island. It is a compilation of horrific crimes against humanity and was the real prep for the Holocaust.
Thank you for commenting this! I was going to bring it up as well, but instead, I might piggyback on your comment if you don't mind. First, the Damara and Nama people are separate people and the Nama are the ones who were specifically targeted and imprisoned on Shark Island. I have no doubt that Damara and others were probably horribly affected by the genocide (not like Germans probably bothered to learn the difference!), there was no official order against them. To add a little more detail to your comment, the Nama and Herero both had extermination orders from von Trotha and through him allegedly from the Kaiser himself. A lot of officers from the GSWA went on to be prominent Nazis. The Shark Island photos alone weren't the only thing that changed in the 90s. Namibia got independence in 1990 and the survivors and decedents were finally able to organize and demand international attention for what happened. Loved the episode and glad to see other folks in the comment knowing about Namibia! Land of the Brave!
I was a little surprised the term Jive-Ass had to be explained. I hope everyone uses it in a sentence sometime soon.
Inadvertently listened to this whole episode at 1.25x speed, it was stressful
It happened to me the other day with a If Books Could Kill episode, and Michel Hobbes sounded absolutely unhinged
Really liked this episode. Learned a lot. I know people who really like Moby Dick but I don’t trust a single one of them. Herman Melville’s books are so fckng boring. And to have his book in the same paragraph as James Joyce and Faulkner is mind boggling to me. But I mean thats just my opinion that I wanted to share. If you like Moby Dick, like one of those “ive read it multiple times” type of people - thats totally cool. You and the guy who shot up Virginia Tech are both tooootally cool. :-p
I started reading it last year, and I was surprised at how great the prose was and how easy to read *most* of it was. I really enjoy the way Melville writes, and most of his chapters are very short, which makes it easy to just knock out another full chapter after you finish one. Once in a while, though, he has chapters that are a lot longer and might be about different types of whales or details about life on a whaling vessel, and while I did find a lot of that interesting, I often read before bed and I would fall asleep in the middle of those chapters, start the chapter over the next night, and fall asleep again. I eventually realized it was really overdue and I needed to do something else at the library, so I had to return it, but I did enjoy most of the experience so far and will try picking it up again soon.
I GASPED at how predictable Jake was in this one. Still litigating Pinkerton’s legacy after all these years
Jake said “the same thing happened when…” and I instantly knew a Weezer reference was coming.
Loved the ep, looking forward to digging back into some Pynchon after a long time away. Great discussion of the writer’s themes. Forgive the pedantry but Eurydice isn’t pronounced like “euro dice”. It’s more like “you RID uh see” 👀
Adding the payments for each book was really eye-opening; thinking about the now trillions of dollars dumped into LLM’s and generative AI, technologies specially engineered to impoverish culture and education, what an incredibly flourishing we could’ve seen if that money had gone towards funding human artists, writers, teachers. Could you imagine a society that had even the tiniest fraction of that capital put into public arts? Goddamn.
Bleeding Edge Erasure, tbh
+1 for Bill Watterson's genius 🙌
Should not have listened to this while jet lagged on a 3 hour drive, David’s voice is too soothing
I love Devin’s episodes a lot. Thanks.
Honestly, Jake's stories have a lot in common with Pynchon.
Fuck yeah!!! Crying of Lot 49 is probably my favorite American novel.
I always loved that Gravity's Rainbow has some of the Christian pablum they had Werner Von Braun say for it's epigraph, only to start with the horrors he wrought the second you turn the page and start the story properly
I love how the first thing that pops into Jake’s head for like something a Nazi would do is watching Indiana Jones but rooting against Indy.
Y'all are on a streak of very good episodes right now
Lmao, I just wanted to point out, the name Takashi Fumamota they mentioned near the end of the episode, in Spanish it means weed-smoker, as in Fuma means to smoke, and mota is slang for weed
Yeah, Fumamota is not an authentic Japanese name. It's possible to create it as a name, but considering that most family names in Japan are pretty limited, it's exceedingly rare at best. I have no doubt he meant it as a pun.
Devin all day everyday, love this guy
It's a tribute to Jake, Julien, and Travis that they've managed to attract such smart people as guest hosts.
Why do middle class straight white men heart DFW? 🥱
I read infinite jest when I was like 21 and my most lit bro opinion is that it is an incredibly profound book. It is taxing and needlessly convoluted, but once you get into the meat of the book about 300 pages in it really gets good. I get why it’s not everyone’s cup of tea but as someone who can be broadly classified as similar to DFW I had never read such personal experiences with depression and addiction and it was a novel I thought about daily for many years. I do think his shtick wears thin and I’m not a reader of his anymore, but I do think he is a good stepping stone to take on more challenging literature
“NASA-American” —Devin, you scamp
Loved this episode! Took me back to my college English major days. I’m on a second listen because I know I missed details the first go around.
This episode was amazing. Different but a nice treat! Love Pynchon
gnosticism mentioned (have u killed god today)
Thanks for the compliment Jake! 😂
TIL Julian is a Philistine ahahahahaha
When will the Bolaño episode drop??
The more I listen to thus podcast, the more I'm disabused of the notion I've ever had a thought that wasn't one many other people have had. I never encountered anyone who had read Pynchon 20 years ago, so I thought I was on to something at least uncommon, but here y'all are. I revel in the connection with y'all, and lament being a sum of cultural influences.
Jacques Ellul has an excellent take on the Technological Society.
So, basically, Brazil by Terry Gilliam.
Gilliam must've been influenced by Pynchon, I'd reckon. Great movie!
As a 20 year fan of pynchon's work I was really hoping for more of the conspiracy theories surrounding the books. But this is a great primer episode to get people into his work.
If you ever want a wormhole to another dimension, check out the Pynchonwiki. His writing is so complex and there are rabbitholes in nearly every line.
I prefer Against the Day (1000+ pages about the years leading up to WWI) and the Crying of Lot 49.
DFW probably does have trouble focusing, as he's dead
I guess I should not be surprised to find out that my stoner friends and my grad school friends are friends with each other! I haven't listened yet but I think of the rainbow in gravity's rainbow as the array of competing explanations of reality or more concretely just exactly where the deadly bombs will fall on London. So I can see the connection. Looking forward to listening to this one.
Learning there’s a new Pynchon novel coming is the news I needed and that anyone else is finding comfort in his work in these times is helping a lot
Definitely was not on my 2025 bingo card! There is hope!
I read ‘I’ve been down so long looks like up to me’ in the 90’s and have never heard reference or mention of it before or since. I’ve asked many people through the years and no one ever heard of it. This was such an amazing episode overall but this reference has tied up so much for me regarding that book and who the author was. I had heard (about Farina) that he died in that motorcycle accident on his way to the book launch? Devin didn’t mention anything about that so I’m wondering if that was a rumour? I LOVE THIS PODCAST
It was a motorcycle accident, but I believe he was leaving the book launch. His wife was Joan Baez's sister. My creative writing professor in college was a big Pynchon fan, and she also talked about Farina.
Eurydice’s name is pronounced like “you-rid-a-see” 😅 sorry that was bothering me Also it was the underworld, not hell
Also “Ooh-roe-Boo-rose” not ooh-RAH-buh-rose
Holy shit!! So stoked for this episode
Great app guys this is why I Patreon’d u
EP
Louis Sachar was just smoking pot and watching TV, while Norton Juster was truly the master with the Phantom Tollbooth. I kid, but Sachar, Juster, Joyce and Pynchon are probably the reason my family love / hates when I talk about books
lol, I’m also a product of the Sachar to Pynchon pipeline. Loved hearing Wayside School mentioned.
Where is Liv Agar?!?
Big if true!!!
I read The Crying of Lot 49 my sophomore year of college in a course that was offered every 2 years. Senior year rolled around and some of my friends took the class and it was on the syllabus again. I got some other friends to help me write "W.A.S.T.E." and the post horn symbol around campus (it was a small school) my friend who edited the campus paper refused to sneak it in to the next edition though. Coward.
After reading CoL49, I was tipsy in a Greenwich Village bar and in the bathroom I spied "Trystero" and the horn. That's when the Pynchon inception began for me.
Two things: 1. No need to re-watch IV, it’s still PTA’s worst movie. 2. More Franzen hate, please. Dude writes dog shit novels for suburban NIMBYs.
Not enough love for Johanna newsome in inherent vice.
Really great episode. It's always great when Devin stops by
First I’d ever heard of Pynchon. Like I just slipped out of an alternate reality, and now there’s this established author that didn’t exist before. I’ve got a lot of reading to do.
Literally a lot of reading. His books are massive...
My mom wrote her PhD thesis on Pynchon and my dad is a big conspiracy theorist so the past two episodes are tailor made to get my parents into the podcast - thanks boys
say more about her thesis if you can, would like?
blows my mind the hosts haven't seen Inherent Vice
Keep all the Pinkerton references! I’ll let others handle correcting the pronunciation of the Greek-derived words.
Actually, now that I think about it, the Pinkertons are recurring Pynchon characters, aren't they? Somehow it all ties together.
Julian ranting about DFW in the present tense - who should tell him?
It's understandable to be unfocused when one has been dead as long as DFW has.
Hell yeah, read Lot 49 and GR last year, both were phenomenal. Glad to see other people showing interest
Michael S Judge
I once went on a date with a guy who said Ulysses was his favorite novel. I should have ended the date right then.
Mentirosa!
As a non-american I never liked Pynchon, it always seemed to me that you needed to grow up in Califirnia in 40s to fully understand him or something. Give me Don DeLillo anytime
I read The Crying of Lot 49 between Christmas and New Years and wanted to underline the whole book. Very excited for the Devin OShae take on this (as with anything)
Episodes like this are why I love this show. Always learning about new stuff I need to check out. 👌🏻
Was not expecting a mention of Sideways Stories From Wayside School. That book had me laughing until I cried when I was a kid and was absolutely formative for my sense of humor
Same. I'm actually reading it right now to my 8yo. Kind of bummed how many times I have to sidebar and explain how something is absolutely not ok (pulling a girls pigtails, kissing a boy who doesn't want to be kissed...) But it is still hilarious.
Rugles the clown
My dad has a long-standing pet theory that Thomas Pynchon is one of the guys in The Residents. Idk how feasible that is but I could believe it, seeing as that band also satirizes American pop culture in their art in strange and inscrutable ways
I've heard that theory before and I think it's got merit!
I’m about halfway through Gravity’s Rainbow and haven’t read that biography yet. I’m thinking that Slothrop’s family history must be a play on his own, right?
Absolutely.
I felt so much rage hearing David foster Wallace name. Was about to skip the episode, then got to hear a nice Julien rant that reminded me why I love this podcast. Julian, you are the best
Especially because he ranted about him as if he were still alive and writing lol
DEVVVVVVVIN O SHHHHEEEEA
📯
Trystero!
Super stoked. Fucking LOVE Pynchon.
Jake Jake Jake
Travis View
Liv Agar