Thomas Pynchon: A Primer

Thomas Ruggles Pynchon has a rare kind of fame: he’s one of the most well-known “recluses”, eschewing the generally standard media engagements expected of a writer of his status. (This is not counting his two appearances on The Simpsons, wearing a paper bag over his head, of course.) As a result, it’s easy to chortle about the man as myth, as a hilarious cad of letters, the one who sent comedian Irwin Corey to accept his National Book Award Fiction Citation  – who rambled aimlessly about “Richard Python” – and when the proceedings were interrupted by a streaker it seemed somewhat, well, appropriate.

As tempting as it may be, first-time readers should avoid Pynchon’s most famous novel: Gravity’s Rainbow. I suspect this is where many bristle against his work, throw down the fat tome and declare this Pynchon fellow to be a literary huckster and a writer who has no interest in writing accessible literature with a proper story. Which, I suppose, he is. But in a good way. One must get used to him: a first-time reader has to walk before they can run. Pynchon’s prose takes gradual acclimation. It’s very easy to finish a scene and be completely unaware of what just happened (obviously if you had been paying attention, you’d know the protagonist was swimming down a toilet, chasing his harp, to avoid Malcolm X). Pynchon’s novels are high-calibre shaggy dog stories, full of digressions and possibly pointless details converging to a climax that resolves little, if anything. Gravity’s Rainbow, for example, has a brief interlude in which we follow the history of Byron the Bulb. An immortal lightbulb. And it’s wonderful. But there’s time for Gravity’s Rainbow later. There are less threatening entry points to Pynchon’s mad world.
For the complete beginner, I would recommend one of two novels: The Crying of Lot 49 or Inherent Vice. The former is by far the shortest of his works, his second book, and the latter is his most recent, coming from nowhere in 2009. Both are set in the dark paranoid underbellies of Sixties America, and both have a relatively straightforward plot. One can dip a toe into the bizarre worlds of Pynchon and adapt to his style gently.

The Crying of Lot 49 follows Oedipa Maas, whose recently deceased ex-lover has named her the executrix of his estate. This slim novella somehow manages to pack in historical conspiracies, more characters than most novels thrice its length, an insane psychiatrist (who boasts of his weaponized facial expressions - he once drove a victim mad), Sixties rock, and Jacobean revenge plays. Oedipa ranks as one of Pynchon’s most composed protagonists, and is an ideal bedrock for strange events to wash over.

By contrast, Inherent Vice’s Larry “Doc” Sportello, a constantly stoned private detective, is a complete shambles. Beseeched by his ex to hunt down her current lover, Sportello and his cohorts are thrown up against the fascistic LAPD and yet another conspiracy. This is the closest Pynchon comes to writing a ripping yarn. Paul Thomas Anderson wants to make it a movie starring Robert Downey Jr. That would be awesome, and it would lend itself to an adaptation in a way that other Pynchon novels wouldn’t. To lower yourself in easily, start with one of these two. Then it’s time to move up a notch.

V. is Pynchon’s debut novel, written in his twenties, and follows two men in a story that crosses sixty years and several continents, all in pursuit of the mysterious “V.”, whatever he/she/it is. The book sets a precedent for the rest of his oeuvre: little is resolved, answers are most certainly not spoon-fed to the vigilant author. But still, it haunts. Connections are made between the disparate strands.

After all, that’s one of Pynchon’s great concerns: paranoia. Or, to boil it down, the drawing together of seemingly unrelated things into a unified whole. When the reader accepts that they have a part to play, in engaging with the text, drawing the threads together and, in the best possible way, doing a little work, Pynchon’s works become so much more enjoyable. Guides exist for almost all of his books, listing the vast array of allusions and references, making it slightly less opaque to the reader less learned than Pynchon (i.e., everybody). The active checking of references – whether by the printed guides or excellent wikis – is a process I would greatly encourage. Soon, after drawing together the divergent characters and narratives, it hits you: finding connections where there may not be any... Pynchon’s effectively made you paranoid. The intimacy it accords the reading experience is transformative, and you’ll come out feeling like the novels are very good friends.

Or even best friends. For the next step in the Pynchon path is the longest of his novels, and probably my favourite: Against The Day. Released in 2006, it loosely follows the Traverse family in the early twentieth century, who avenge their anarchist father’s murder by a ruthless capitalist named Scarsdale Vibe. On the surface, that’s the plot. There are frequent forays elsewhere. The novel is extremely parodical, without ever becoming cloying. We are often placed in the company of the Chums of Chance, a group of adventurers aboard the airship Inconvenience (to say nothing of their talking dog), who drift in and out of the main storyline, the narrator occasionally interjecting with a reference to another one of their adventures (and the title; they are straight out of a “boy’s adventure” tale, and are recognized by other characters as such). Historical characters pop up here and there. Franz Ferdinand acts like a complete racist jerk. Sentient ball lightning and hollow earth and Tesla and each thing I type is making me want to slap down the screen of my laptop and start reading it again. Dense and weird, but utterly amazing.

After that? It’s probably time for Gravity’s Rainbow. The basic plot? Well, as we’ve established, that’s not saying much. In the dying days of WWII (and just after the German surrender, with Europe a shapeless “zone”) is an American GI stationed in London named Tyrone Slothrop. He’s a bit of a ladies’ man. On his cubicle wall is a city map, with stars dotting his sexual conquests. But Slothrop’s being observed... for every one of those stars later becomes the spot where V2 rockets (so fast that it’s only heard after it’s landed) crash down. We’re not even 100 pages in. Superheroes, scatology, tarot and mad Nazi scientists. It’s all here. Hundreds of characters come and go, telling their own stories before vanishing. I’ve already mentioned Byron the Bulb. The Pulitzer Prize board refused to award the book; is there any better recommendation? Another shaggy dog story it may be, and often incoherent, but a truly unique literary experience. One of the most monumental in my reading life, and a masterpiece.

There are other works. Slow Learner is a collection of his previously uncollected short stories, and frequently prized more for the self-penned introduction within, rather than the fictions themselves. Vineland, released in 1990, featured a paranoid ex-hippie adrift in Reaganite America. There was a seventeen year gap between Gravity’s Rainbow and Vineland. It’s generally considered his weakest.

And finally, Mason & Dixon: a self-conscious and strange novel that has its fervent admirers. The journeys of the titular astronomer/surveyor duo are told by their acquaintance, the Reverend Cherrycoke, on a winter’s evening for the amusement of his family. The language utilizes the syntax, spelling and register of an actual document of the era, a format Pynchon has no qualms about undermining: something that is described as splitting in two corrects to “actually, twain.” Cherrycoke’s position in the household relies on his being entertaining, and so the direction of his story alters depending on his audience. Although a wonderful book (and one I’m still digesting) the intentionally archaic language can be daunting, and I would recommend saving this one for later.

Beginning to read Thomas Pynchon is a commitment, but not one that should be feared. The effort is well worth it. Masterpieces await you, equal parts funny and moving. Embrace the meandering strangeness of the plot, the hundreds of characters, and the surreal digressions. Allow yourself to get lost in them and find your way later. The struggle to force it all to make sense is futile, in the best possible way. As Benny Profane says when looking back at his adventures in V.: “I’d say I haven’t learned a goddamn thing.”

I’ll end with perhaps the best summary of Pynchon’s fictional mindscape that I can find, excerpted from the author’s own forward to Against the Day:

“If it is not the world, it is what the world might be with a minor adjustment or two. According to some, this is one of the main purposes of fiction.

Let the reader decide, let the reader beware. Good luck.”

(Side note: As for guides, Steven Weisenburger’s is fantastic for Gravity’s Rainbow, while J. Kerry Grant has great ones for The Crying of Lot 49 and V.)

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Jack Joslin

Column by Jack Joslin

Jack is a graduate of the University of Warwick. His current project is a surreal biography of the band Paris and the Hiltons. He lives in the UK, where he founded the netlabel Portnoy Records. He can't juggle yet, but really is trying very hard. Often he tells people he's ten feet tall, even when they're standing in front of him, which makes for awkward pauses. He writes incoherent thoughts and opinions at the International Society of Ontolinguists.

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misterwoe's picture
misterwoe from Kansas but living in Athens, Greece is reading Perdido Street Station by China Mieville, Inside the Third Reich by Albert Speer, A Wolverine is Eating My Leg by Tim Cahill April 26, 2012 - 12:37am

Excellent write-up. I love Pynchon, and I would say Against the Day is definitely my favorite so far. As you mentioned, the secret to tackling his bigger masterpieces is not to worry about making sense of everything and just enjoy each page. The work in a lot of ways is unhinged, so the reader has a chance to and yet must unhinge oneself. You know what I mean? There were times when reading Against the Day, I stopped and scratched my head, man what am I reading am I hallucinating this right now? Remember the scene with the parrot label hot sauce?

Joshua Chaplinsky's picture
Joshua Chaplinsky from New York is reading Library Books April 26, 2012 - 6:27am

I was defeated by Gravity's Rainbow as a college Freshman, but have read a bunch of his stuff since. You're spot on about Lot 49 and Inherent Vice being great entry points.

misterwoe's picture
misterwoe from Kansas but living in Athens, Greece is reading Perdido Street Station by China Mieville, Inside the Third Reich by Albert Speer, A Wolverine is Eating My Leg by Tim Cahill April 26, 2012 - 11:30am

I also want to add that Pynchon's novels have a magic to them unlike anything I've ever read.

Scott Williams's picture
Scott Williams from Brooklyn, NY is reading 11/23/63 April 30, 2012 - 12:04pm

Mason & Dixon was the first Pynchon book I actually managed to make it all the way through. It has an emotional core, the story of the friendship between the two titular characters, that I felt was missing from much of Pynchon's work. The language is archaic, certainly, but like some poetry, a short learning curve is all that's required to learn the ground rules. I found it rather charming, actually.

Gravity's Rainbow is dazzling, though I haven't felt the urge to read it again since I finished it ten years ago. And I still haven't made it through V. 

Jeff's picture
Jeff from Florida is reading Another Side of Bob Dylan by Victor Maymudes May 4, 2012 - 5:57pm

 His prose is hypnotic. I really got deeply into V. It was my introduction to picaresque.  Not only  Benny Profane (the lead character and self-described human yo-yo), but the Gaucho too, is such a strong comic character -- so deadpan -- so ready to fly into battle, like a Don Quixote.

I think what you said about his novels becoming very good friends is right. He mythologizes at will. Who wouldn't want a pal like that to hang out with?

Edward Young's picture
Edward Young June 14, 2013 - 6:03pm

It's funny, because he went to my church, and his dad was a member of the vestry and friends with mine. Even though he is a generation older than me, I can't believe I wandered around in many of the places he did. Where did his oeuvre come from? Sui generis.

Ears's picture
Ears June 6, 2020 - 10:54am

The author is exactly wrong and simply voices his own opinions without much support - he also sounds like Donald Trump when he says that – noting, first that he uses the horrible passive voice – when he says that Vineland "is generally considered" the weakest work – it is a shit ton better than Inherent Vice, which is a messy pastiche and far and away his worst novel, and it is the best primer for Pynchon's themes and style. It is also the most accessible.

There's also nothing with starting with Gravity's Rainbow, so long as you need it small bites at a time, maximum 10 pages at a sitting, and which is also beautiful, important, and powerful, Mason & Dixon is simply absolutely gorgeous, and Bleeding Edge is the best novel to come out in the last 10 years.