One Punk’s Guide to Pynchon Novels

One Punk’s Guide to Pynchon Novels By Sean Carswell

Oct 18, 2018

One Punk’s Guide to Pynchon Novels originally appeared in Razorcake #100, released in October/November 2017.

Here is a printable PDF and full text of the article.

Illustrations by Brad Beshaw
Original layout by Todd Taylor
Zine design by Marcos Siref.

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One Punk’s Guide to Pynchon Novels

By Sean Carswell


I stole my first copy of a Thomas Pynchon novel. I was at a flea market in the student union of Florida State University, the summer of 1991. I saw a battered copy of The Crying of Lot 49. The front cover would need tape to survive another reading. The margins were littered with the type of comments an undergrad writes while taking notes in class, wondering if this shit will be on the test. The price: 45¢. I read the first line of the book at the stand:

One summer afternoon Mrs. Oedipa Maas came home from a Tupperware party whose hostess had put perhaps too much kirsch in the fondue to find that she, Oedipa, had been named executor, or she supposed executrix, of the estate of one Pierce Inverarity, a California real estate mogul who had once lost two million dollars in his spare time but still had assets numerous and tangled enough to make the job of sorting it all out more than honorary.

What? Kirsch in the fondue? Housewives getting drunk off spiked cheese? Correcting executor to executrix? Is executrix a real word? (It is). A novel about divvying up assets with this much energy and madness in a sentence? I was sold. Only, this was a time in my life when 45¢ was a little more change than I could spare. I intended to put the book back and check it out from the library, which was on the way home anyway. The guy who ran the book stand said something smart ass to me. I nodded, put the book down, and flipped through another box until he turned his head. I slid the book into the pocket of my plaid bermudas and headed home.

The next several hours were spent reading the book without a break. It’s so complex, with so many characters and plot threads to keep in mind, and so many scenes that make you stop and say, “Wait, did I just read that?” I felt like, if I put it down, I’d forget the one key piece of information I needed to make sense of this madness. It was sometime around 2 AM when I got to the end. I realized that I’d forgotten or lost track of several key pieces of information. This novel, like life itself, was too massive to wrap up tightly at the end. It’s full of loose threads, leads unpursued, roads not taken, cul-de-sacs, and the overriding sense that there’s something bigger—maybe more sinister than we can or want to imagine— out there, playing us like we’re monkeys in front of an organ grinder’s piano.

One Punk’s Guide to Pynchon Novels

This is the first great thing about a Thomas Pynchon novel: it invites us to see life with more complexity. The world around us is chaos in the purest sense. If we get even a little philosophical, we see that we understand less than a tiny fraction of nature, life, meaning, language, societies, cultures, and ourselves. We construct narratives to make this tiny fraction of understanding seem bigger, more unified, to help us forget that what we know is a small drop in the giant sea of what we don’t. It’s scary to get beyond our narratives and dip our toes in the unknown. Pynchon helps us with that. His novels lead us up to that giant sea of the unknown. They slide our shoes off and seduce us. “Go on,” they say. “It’s just a toe. Dip it.”

I was so excited when I finished The Crying of Lot 49 that I crashed into my roommate’s room to tell him about it. Luckily he was alone in there. Awake. Not jerking off. He let me tell him about what I’d just read. Thank god he did. I had to put my thoughts into words or I never would’ve been able to sleep. I was so stoked by the book that he got inspired. The next morning, he started in on The Crying of Lot 49. He gave up after the first page.

This is the second thing about a Pynchon novel: it’s not for everyone.


Since my first encounter with The Crying of Lot 49 more than a quarter of a century ago, Pynchon’s novels have been for me. I’ve read all of them several times. The two topics I’ve written about most in my adult life are punk rock and Pynchon novels. On the punk side, I wrote a column for the first ninety issues of this zine. Before that, I wrote for Flipside for five years. I’ve churned out literally thousands of band interviews, record reviews, and essays for zines. During that same time, I’ve written articles on Pynchon’s works for some of the most prestigious academic journals in the U.S. and U.K. I’ve given papers at international Pynchon conferences in France and England. I spent eight years writing a monograph—a single-authored academic text—on Pynchon’s conception of global power and resistance to that power. The book is called Occupy Pynchon. It’s the deepest I’ve dipped my toes into that giant sea of the unknown. It’s the most significant work I’ve done in my life. Occupy Pynchon came out in May 2017. The whole time I was writing it, Todd was asking me to do a One Punk’s Guide to Pynchon. I’m finally acquiescing.

Pynchon for punk rockers is tough. First, I think most punk rockers would like Pynchon’s novels. They charge at you going one hundred MPH. You have to learn how to experience them, how to pick meaning out of the madness. In that sense, reading Pynchon is like listening to a hardcore record. Pynchon’s works are full of dick and fart jokes, silly puns, stupid names, and radical politics, just like a lot of the punk rock albums I have. And, in some large categories—community building, anarchist DIY leanings, art that rejects global consumer capitalism—what makes Pynchon’s novels and punk rock great are similar. But let’s be clear. Thomas Pynchon is no punk rocker. In fact, he is part of one group that, until the mid-nineties, was punk rock’s mortal enemies: hippies. He’s also part of another group that still is punk rock’s moral enemy: rich people.

Thomas Pynchon was born in 1937 in New York. His father was an upper middle-class guy, an industrial surveyor and, for one year, city supervisor of Oyster Bay, New York. Pynchon attended Cornell University for two years, joined the Navy, then returned to Cornell, where he graduated in 1959. His Ivy League connections helped him get his early work published. One of his professors introduced his work to Nobel Prize-winning author Saul Bellow, who published one of Pynchon’s first short stories. These publications allowed him to secure the services of one of New York’s most powerful agents, Candida Donadio. Donadio also represented Joseph Heller (Catch-22) and Mario Puzo (The Godfather). In the seventies, Donadio reportedly scored Pynchon a million-dollar advance on a two-book deal. Around that time, one of Donadio’s employees, Melanie Jackson, convinced Pynchon to jump ship and join her new agency. Sometime in the early eighties, Pynchon and Jackson married. Now, Jackson is a heavy-hitter in publishing, representing boring, painfully bourgeois authors like Rick Moody and Lorrie Moore. At one point in Pynchon’s Inherent Vice, a wealthy and sinister character explains to the protagonist that the most important thing to maintaining wealth and power is “being in place.” Pynchon is firmly in place.

He’s widely viewed as a recluse because he doesn’t do interviews, allow himself to be photographed, or give public appearances. This has led to rumors that he’s really J. D. Salinger or the Unibomber or whomever. The rumors can be fun, but they ignore the fact that a lot is known about the guy. He lives on the Upper West Side of Manhattan. He goes out to lunch with writers like Don DeLillo and Salman Rushdie. He did two guest appearances on The Simpsons. A few people who’ve met him have written about him, most notably Jules Siegel in an article titled “Who Is Thomas Pynchon… And Why Did He Take Off With My Wife?”, which ran in a 1977 issue of Playboy, and Andrew Gordon in his essay “Smoking Dope with Thomas Pynchon,” which was included in the collection The Vineland Papers. In these two works we find out that Pynchon did, indeed, take off with Siegel’s wife and smoke dope with Andrew Gordon. All the biographical information on Pynchon amounts to this: he’s a guy who writes books. The books seem to be the most interesting thing about his life. Let’s focus on them.


Pynchon’s first novel is V. It came out in 1963, when Pynchon was twenty-five. It won the William Faulkner Foundation Award and was a huge critical and commercial success. It tells the story, first, of Benny Profane, a recently discharged sailor who’s cultivating the life of a human yo-yo. He bounces around from job to job and place to place, sleeping on couches, hanging out with a bunch of bohemians who call themselves the Whole Sick Crew, and delving into relationships with various women who want to save his lost and doughy ass. From all I can gather, Profane was modeled after Pynchon himself. Pynchon also yo-yoed around New York and the northeast corridor, hanging out with old Navy and college buddies, one even named Pig Bodine like a character in V. (and, later, Gravity’s Rainbow). Friends of Pynchon from the late ‘50s and early ‘60s even referred to their group as the Whole Sick Crew. The most entertaining parts of the Benny Profane sections of V., though, are the ones that deviate from autobiography. For instance, Profane spends a chapter hunting alligators in the sewers under Manhattan. While underground, he discovers a shrine for (and subsequently reveals the history of) a patron saint of sewer rats. It’s strange and funny and philosophical.

If the novel alone were just about a dude in his early twenties wandering around lost and getting drunk with his buddies, it would probably be long out of print and forgotten. What makes V. special and sets Pynchon apart from his contemporaries are the alternating sections in which the other protagonist, Herbert Stencil, searches for the mysterious V. V. is a manifestation of the old White Goddess myths and perhaps a spy who tangled with Stencil’s father. His search for V. takes the novel through Egypt, South Africa, and various points in Europe. What Stencil can reconstruct of her movements and her possible life allows readers to venture into the upper echelons of power and colonialism that led to the first World War. Eventually, Profane and Stencil team up and plan to travel to Malta, where they try to solve the mystery of V. I’m not spoiling anything to tell you that the mystery is bigger than the novel. In my five or six readings of V., I’ve learned an incredible amount about global power, capitalism, psychology, jazz, art, apartheid, and slavery, but I’m still not quite sure who V. really is or if she’s really just one person.

I first read V. when I was twenty-four, right around the age Pynchon was when he wrote it. I was living in Atlanta and wrapping up the first draft of my first novel, Drinks for the Little Guy. Coincidentally, I had characters like Profane and the Whole Sick Crew. I had the lost and drunk dude in his early twenties, a mostly autobiographical portrait. After reading V., I felt like I had to make my novel bigger, tie it into global politics, go into the speculative realms of alligator hunting and patron saints of sewer rats. I spent a year trying and failing to do that. I finally gave up and made the novel the book I’d set out to write. Pynchon had already written V. I didn’t need to be some kind of referential wannabe.

His other sixties novel is The Crying of Lot 49. As I’ve said before, I started this one that follows Oedipa Maas as she tries to execute a real estate mogul’s will. Doing so, Oedipa stumbles across the Tristero, which may be a massive conspiracy, a massive practical joke, or a look inside her own insanity. It’s a short book, but it has enough room to include a satirical Jacobean play, a Beatlemania band called the Paranoids, several goofy songs (only one or two of which are Paranoids originals), right wing fringe groups, and a perhaps centuries-old postal underground.

Most people who want to read Pynchon start with The Crying of Lot 49. It is, after all, the shortest. It’s also one of the most difficult. When I was writing my dissertation on Pynchon, my dissertation director, who’d read several Pynchon novels and is a brilliant scholar, asked me if I could explain The Crying of Lot 49 to him. He said, “That’s the one book I can’t get my head around.”

Him and everyone. When I got into Pynchon, there were only four novels to choose from (and only one that could fit into the pocket of my bermudas). Since then, Pynchon has written four more novels, all of them easier to read than The Crying of Lot 49. I’ll say it here and again later: if you’re unsure about Pynchon, start with Inherent Vice. It’s not very intimidating, and it’s a lot of fun.


Pynchon followed The Crying of Lot 49 with Gravity’s Rainbow in 1973. If you’ve heard of Pynchon, this is probably the novel you’ve heard of. Many consider Gravity’s Rainbow to be Pynchon’s masterpiece. It won the 1974 National Book Award. Pynchon, who long shunned the public eye, refused to attend the ceremony honoring him. His publisher sent comedian Irwin Corey instead. Corey delivered a bizarrely funny monologue accepting the award. He never identified himself, and many in the crowd, having never seen a picture of Pynchon and knowing the book to be bizarrely funny, thought the comedian was the author. As you might expect, this pissed off a lot of literary types. The judges for the Pulitzer committee also selected Gravity’s Rainbow for the 1974 prize, but the advisory committee decided they’d rather not give the award that year than give the award to this book they called obscene. The Irwin Corey episode is probably the reason why Pynchon, who is widely regarded as the greatest living writer, has never won the Nobel Prize for literature.

Gravity’s Rainbow’s plot, if it can be said to have a plot, follows American lieutenant Tyrone Slothrop through the final days of World War II. British military intelligence has discovered a correlation between Slothrop’s erections and the German V-2 rocket, which is bombing the shit out of London. Hijinks ensue. I really don’t want to summarize it better than that. It’s a book that rejects any simple characterizations. It has everything you can imagine and more. Kazoo choruses. Pavlovian-trained octopi. Coprophagia. Séances. Pig superheroes. Hash on Harry Truman’s windowsill. Custard pie fights. Love. Sex. War. More than you ever thought you wanted to know about rocket bombs. It’s part spy novel, part war novel, part thought experiment, part history, part whimsy, and, overall, an exploration of humanity’s hard-on for its own final destruction.

I read Gravity’s Rainbow for the first time when I was twenty-five. My fellow Razorcaker, Jim Ruland, read it at the same time. We’d get together and smoke weed and drink beer and try to make sense of what we just read. Even factoring in all the beer and weed, I came out of my reading experience smarter than I started. More than that. There was a version of me that existed before reading Gravity’s Rainbow and a second version of me after reading it. A paradigm shifted. I became not just a person, but a person connected to history and global power, a person able to think in real ways about what it meant to be alive at the end of the twentieth century.

I wouldn’t recommend starting with Gravity’s Rainbow. Again, start with Inherent Vice. But set aside two months between now and death to read this book. The sooner, the better. And, if you’re like me, you’ll go back and read it again every few years. So far, it’s been better with each read.


After Gravity’s Rainbow, Pynchon didn’t publish another novel for seventeen years. In 1984, he released a short story collection, Slow Learner. In the introduction, Pynchon disparages the stories in the collection. Part of that is false humility. Part of it is honesty. It’s not a great book. The stories were all written while he was in college. They read like they were written by a kid in college. A brilliant kid, but a kid. If you’re getting into Pynchon, Slow Learner is a good book to read after you’ve read everything else.

The first novel after Gravity’s Rainbow is Vineland, which came out in 1990. On the surface, Vineland is much simpler than Gravity’s Rainbow. Gravity’s Rainbow is encyclopedic. It has everything from dodo hunting to rocket science in it. Reading it is a journey. Vineland takes on television, pop culture, and the legacy of sixties activism in Reagan’s America. Critics and fans who wanted Gravity’s Rainbow 2, attacked and dismissed Vineland.

I totally disagree with that.

In the seventeen years between these two novels, something happened in the world. We don’t talk about it as such, but a revolution occurred. It left us all on the losing side. With the election of Ronald Reagan in the U.S. and Margaret Thatcher in the U.K., with the rise of Deng Xiaoping in China and Paul Volcker as the chair of the Federal Reserve, global power began to shift. Behind this was an ideological shift. For the first time in human history, huge masses of people began to believe that life should be about accumulating consumer goods. Gain, wealth, and money came to supplant meaning. The concerns of the marketplace became societies’ primary concern.

Political discussions started to include terms like “deregulation” and “big government” and “free market,” all empty signifiers, words that mean nothing. Those in power didn’t believe in actually taking away regulations or making the market free or shrinking the overall size of government. They instead wanted to change regulations to favor a small network of wealthy individuals at the head of multinational corporations, national governments, and supranational agencies like the World Trade Organization, the International Monetary Fund, and the World Bank. The role of government, according to those in this network, should be to improve the lives of those in this network. This ideology, as a whole, goes by the name “neoliberalism.” It’s a new form of economic liberalism, which was first championed by Adam Smith in The Wealth of Nations. Unlike Adam Smith, who actually believed in free markets, neoliberals simply used the terms and concepts of economic liberalism as a sales pitch for funneling money upward.

Pynchon tapped into this power shift immediately. The real genius of Vineland is Pynchon’s ability to formulate a resistance to the neoliberal revolution a decade before small groups of people started working against it at the WTO protests in Seattle in 1999, two decades before Joseph Stiglitz and the Occupy Movement came up with the term “the 1%.” Vineland isn’t intellectually light or a regression from Gravity’s Rainbow. Instead, Pynchon was exploring how working and middle class Americans were getting fucked by big business and governments just as the real fucking was beginning. Now that we’re living in the third decade of this fucking, the novel’s brilliance shines brighter.

I should also say, it’s a fun book with great characters. There’s a Japanese monster movie scene, a mountain retreat full of feminist ninjas, a radical film collective, old hippies and new punk rockers, and even some Wobblies still hanging around. It’s also the first time Pynchon really learned how to end a novel. The ending of Vineland is worth the price of admission, even if you want to ignore all the neoliberal stuff I just talked about.


In 1997, Pynchon published his second encyclopedic novel, Mason & Dixon. As the title indicates, the novel is about Charles Mason and Jeremiah Dixon, the astronomer and surveyor who drew the boundary between Pennsylvania and Maryland known as the Mason-Dixon line. It follows Mason and Dixon’s adventures first to South Africa, where they charted the 1761 Transit of Venus (when Venus is visible passing across the surface of the sun, charting it was used at the time to determine the exact shape of the Earth). They’re then sent to the United States to reconcile this impossible border which came to designate the divide between free and slave states. Dixon—who in real life was a Quaker and ardently anti-slavery—became the namesake of Dixie, the slave states. The novel follows the characters until their respective deaths after the Revolutionary War.

Mason & Dixon is my favorite Pynchon novel. It blends the styles of early American literature that I love: the gothic novels, the captivity narratives, the historical romances that were prevalent from just before the revolution to just before the Civil War. Charles Mason and Jeremiah Dixon are the most realized of Pynchon’s characters. The end of the book, with Mason and his sons, just might bring tears to your eyes. And what Pynchon does with this period is as funny as it is poignant. Mason and Dixon smoke weed with George Washington. Ben Franklin helps them bargain down the price on opium. Thomas Jefferson plagiarizes a toast that Dixon raises. All this blends with the horrors that paved the way for our lives here: the genocide of Native Americans, the nation’s wealth built on slavery.

Pynchon followed up Mason & Dixon in 2006 with the largest of his encyclopedic novels, Against the Day. Against the Day weighs in at nearly 1,100 pages of small type. Read it, and you’ve really done something. I once taught a course at my university on this book alone. Even though it was the only book we read all semester, even though we spent forty-five hours talking about it in class, even though I taught a great deal about the history and philosophy upon which the novel is based, the general consensus at the end of the semester was that we’d just scratched the surface. It’s that rich of a book.

One Punk’s Guide to Pynchon Novels

Against the Day
spans the years from the Chicago World’s Fair of 1893 through the years just after World War I. Most of the novel follows a family, the Traverses, and their journeys from Colorado mining country to the greater world. The family patriarch, Webb, is an anarchist bomber. After a plutocrat has Webb assassinated, his four children—Reef, Frank, Lake, and Kit—alternately become entwined with and revolt against the forces that led to their father’s death. They become part of the build-up of the first World War. They fight in the Mexican Revolution. They study advanced mathematics, work in early Hollywood, travel to other dimensions, join anarchist collectives, spy for and against national governments, get stuck in Balkan civil wars, blow shit up, and a million other things. The novel reaches its climax in Ludlow, Colorado, where, in real life, John Rockefeller raised a private army and led a one-sided war against his employees. Pynchon breathes life back into this horrible and forgotten chapter in American history. Jesse Traverse, Reef’s son, comes out of it with the greatest definition of what it means to be an American that I’ve ever read: “It means do what they tell you and take what they give you and don’t go on strike or their soldiers will shoot you down.”

Against the Day is my second favorite Pynchon novel. Just writing about it now makes me want to read it again.


Pynchon’s two most recent novels are far less ambitious than the four from Gravity’s Rainbow to Against the Day. In 2009, he came out with Inherent Vice, a detective novel set in 1970. Private eye Doc Sportello is hired to find a missing real estate mogul and solve the murder of the mogul’s bodyguard. The investigation takes him into the lair of a sinister organization called the Golden Fang. In the novel, the Golden Fang is an excellent illustration of that networked power that came to be after the ‘80s neoliberal revolution. They’re a vertically integrated heroin dealer, covering everything from the drug to the rehab centers and dental clinics that replace your teeth once the heroin leeches the calcium out of them. They’re also tied to the FBI, Southern California land management, the U.S. military; power stretching up to Richard Nixon and over to Southeast Asia. To understand the Golden Fang is to understand the inextricable relationship between politics and money in the industrialized world. Doc does his best to wrap his mind around it.

Inherent Vice was the first Pynchon novel to be adapted into a film. In 2014, Paul Thomas Anderson directed his adaptation, starring Joaquin Phoenix, Owen Wilson, Josh Brolin, and Reese Witherspoon. It’s a good movie. I enjoyed it. Everyone I know who watched it and hadn’t read the book was thoroughly confused by the plot. I thought it was pretty easy to follow. My first reaction was, wow, Pynchon’s simplest novel is simplified even more in a film adaptation and it’s still too complex for most people. I taught Inherent Vice after the movie came out. I overheard two students talking before class. One said to the other, “Just read the book. It’s way easier than the movie.” I say, do both. Read the book, first. It’s better if you don’t see Doc as Joaquin Phoenix and Coy Harlingen as Owen Wilson in your head. It’s best if you experience the complete Golden Fang and not the abridged movie version. Then see the movie and think of it as art inspired by art rather than a visual representation of the novel.

And, again, this is the Pynchon novel I recommend you start with. Unlike most of his works, Inherent Vice has one main character who is in every scene. It has a plot that you can follow (if you want to; it’s more fun to me when I forget the mysteries we’re supposed to be solving). You can get most of the allusions without having to look them up. Part of me thinks that Pynchon wrote this book as a gateway into his other novels, a way to get the feel of his works without overwhelming you.

Pynchon’s latest novel (as of this writing) is Bleeding Edge (2013). It’s another good one to start with for all the reasons I just listed. It follows fraud investigator Maxine Tarnow as she explores all the dirty dealings that characterize the beginning of the twenty-first century. There are global conspiracies, Bill Gates-style tech villains, underhanded real estate deals, vaguely criminal venture capitalists and stock brokers, and a battle for the soul of the internet. The novel takes place in Manhattan in 2001. Of course, the year includes the events of September 11. Pynchon gives various characters’ various reactions to the events. They become folded into the larger issues of wealth and power.

I enjoyed Bleeding Edge quite a bit. I’ve read it three times already. I recommend it. Still, among Pynchon’s eight novels, this one is the least impressive to me. At one point in The Crying of Lot 49, Oedipa Maas looks at ancient illustrations that the narrator describes as having been “executed with that crude haste to see the finished product that marks an amateur.” Pynchon is no amateur, and Bleeding Edge is still one of the best novels of the past five years, but it seems to be written with a crude haste. In his previous novels, Pynchon’s research is spotless. In Gravity’s Rainbow, he gives actual physics equations from actual German textbooks teaching rocket science, and he uses them as poignant metaphors. In Against the Day, he explores fourth-dimensional mathematics in ways that are mathematically sound. But in Bleeding Edge, his representation of computer science is spotty. His fictionalization of the Ludlow Massacre in Against the Day casts American labor history into a new light. His representation of 9/11 in Bleeding Edge doesn’t break any ground I haven’t seen broken already. If this is his last book, I’ll be a little disappointed.


Pynchon turned eighty this year. It remains to be seen whether he has something else up his sleeve. We know he tends to write more than one novel at a time. His personal letters show he worked on Mason & Dixon for more than twenty-five years. He wrote The Crying of Lot 49 while deeply involved in Gravity’s Rainbow. So there may be one more big, encyclopedic book before he slips off this mortal coil. And maybe there isn’t. It’s almost greedy to ask for more. His four novels, from Gravity’s Rainbow to Against the Day, are four of the greatest books ever written. Even his lesser books are only lesser by Pynchon standards. They’re still better than anything that came out this year. Eight great novels, man, that’s one hell of a career. But as long as he’s alive, I’m praying for number nine.

One Punk’s Guide to Pynchon Novels

In the meantime, I recommend you give him a try. Pick any one and read it. Don’t worry about “getting it.” Art that you get the first time you experience it is boring. Art that confuses and frustrates and entertains and teaches and leaves you thinking and wanting to go back to it, well, that’s the good stuff. That’s what life is about. So go ahead. Dip your toe into the great unknown. You won’t drown.


Sean Carswell is the author of seven books, including the novel Madhouse Fog, the short-story collection The Metaphysical Ukulele, and the nonfiction book Occupy Pynchon. He is one of the founders of Razorcake magazine and Gorsky Press. He’s an associate professor at CSU Channel Islands.

Brad Beshaw’s illustrations and writings have been published in Razorcake, The Stranger, and Paste, among others. He owned a zine/small-press book shop from 1994 to 2006, and his bands, including Luxo Champ, and Steel Tigers Of Death, have been enjoyed by dozens. He once sold a 2 headed cow to Neil Patrick Harris.


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