Sex, Drugs and the Postal Service: Thomas Pynchon, A Beginner's Guide

With 'Inherent Vice' out in theaters, there's no better time to dive in to the literary giant's doorstopping novels and brain-boggling loops

Joaquin Phoenix and Benicio Del Toro in 'Inherent Vice.' Credit: Everett

Improbably, and with a giddy-making "WTF," the dense prose of author Thomas Pynchon has finally made it to the big screen. Not through the efforts of a bunch of nobodies, either: Inherent Vice, a Seventies-set stoner mystery, stars America's finest working actor, Joaquin Phoenix, buried snout-deep in the author's signature paranoia and hippie haze (as well as some fearsome mutton chops). Writer-director Paul Thomas Anderson, the genius behind Boogie Nights, Magnolia and There Will Be Blood, has emerged as a kindred spirit to Pynchon's loose-limbed funkiness and expansive interconnectivity. The movie looks and feels luscious — it's a unicorn of artistic freedom backed by big-studio support.

And still, even with all these hearts and minds in the right place, it's possible to emerge from Inherent Vice — a two-and-a-half-hour whatsit unlike anything Hollywood has ever tried — with a furrowed brow. You will not understand it. You will not "get" it. You will be carried along to a land of profound weirdness by Anderson's panache and a frighteningly committed cast (one that includes a coke-snorting Martin Short). You will not get your money back.

So take it from the legion of Pynchon obsessives who have loved it: Welcome to the club. This is precisely the mood that the 77-year-old writer has labored to create over eight revered novels and novellas since the mid-Sixties, pushing his adventurous readers off their pedestals of narrative security and trust in government. "He's fucking with you all the time," Anderson recently said of the “anonymous” novelist — the last publicly circulated picture of the author dates back to 1955 — and he means this as a compliment. At a slender 370 pages, Inherent Vice is the quickest way into Pynchon's oeuvre, itself the wildest adventure in postmodern letters. (The collected hardcover editions of his books weigh as much as an unruly eight-year-old in need of a nap.) So maybe it’s time to try him out. The good news: You're already halfway there if you live for rock & roll, enjoy a good conspiracy story and can go with the voluminous flow.

I'm with the band: Doper ditties, sea shanties and surf rock
Before the 2009 publication of Inherent Vice, the usual plunge into Pynchon began with his second work, the 1966 novella The Crying of Lot 49, slim by his subsequent standards. (At the time, the author was working on four other manuscripts that would evolve into epics.) Crying remains a beautiful distillation of everything Pynchon does well: a jokey yet elaborate mystery concerning the postal service, of all things, laced with drugs, sex and anchored by the free-spirited Oedipa Maas, one of the writer's strongest heroines. While reading Crying, it's easy to see it in your head as one of those black-and-white Godard movies starring Anna Karina, herself, like Oedipa, a cool appraiser of comparatively unhinged men. 

By far the funniest takeaway from Crying is its piss-take on Beatlemania, embodied by a struggling band of American teens called the Paranoids who insist on singing in British accents. Commit to Pynchon, and you will discover an unapologetically silly lover of pop songs. His text frequently breaks off into indented lyrics for completely fictional hits, spinning in a jukebox of his imagination. Inherent Vice makes a meal out of surf rock, featuring a slew of references to forgotten twangy classics from real-life bands such as Johnny and the Hurricanes, the Chantays and the Trashmen, along with stirring in a devoutly Christian tube rider who literally walks on water. (The largely faithful movie version doesn’t include the messianic moondoggie, but does find room for the book's properly paranoid sax soloist played by fully-baked Owen Wilson) The takeaway is a bone-deep commitment to late-Sixties beach culture, a false innocence under which the author can brew his ill goings-on. Meanwhile, in the dazzling Mason & Dixon — Pynchon's 1997 riff on Revolutionary-era American history — he somehow crams in a verse about Chinese food into his main characters’ salivating mouths: "Peppers as hot as the Hearth-sides of Hell / Things that Papa has neglected to tell!"

Do these tunes mean anything? Nope, wonderfully not. But don't confuse Pynchon's frequent embrace of sing-along humor for a mere palate cleanser. His ambitious novels are thick reads, studded with references to arcane technical texts, politics, ancient in-jokes and secret historical episodes. When pop culture does emerge, it's often used to make the obliquely critical point that such things often distract us. Oedipa's estranged husband in Crying, "Mucho" Maas, becomes a disc jockey at the fictional radio station KCUF and, in between platters, descends into an LSD-fueled mental mush. That said, Pynchon can't help but have a little fun with his musical musings — his vinyl collection must be frightening.

"He's fucking with you all the time," Anderson said of the novelist — and he means this as a compliment.

Blinded by science: Secret worlds connected, systems within systems
Rolling Stone's Peter Travers, in his review of Inherent Vice, calls the author's colossal Gravity's Rainbow "the Pynchon mountain, the Old Testament of cyberpunk." It's a novel we should never hope to see a movie come from, because losing yourself in its folds is a Joycean pleasure that can only happen on the page. Pynchon's legend, his scary totality of accomplishment, is secured with this 1973 book. It's set during the tale end of WWII and its aftermath, but describing Gravity's Rainbow so concisely is almost to miss the point. It isn't some sentimental war story, but a highly detailed, near-encyclopedic compendium that goes deep into V-2 rocket technology, secret Nazi collaborations with U.S. corporate interests, the dawning atomic age and a kind of fascist dystopia. It's not an easy read.

Take a breath. You made it through Inherent Vice and The Crying of Lot 49. The simplest way into Gravity's Rainbow is via Page One — but it helps to have to a prior appreciation of one of Pynchon's key themes, the clash between high technology and a near-mystical world of secret science, created in private labs that the author likes to invent. Metaphorically, a book like Gravity's Rainbow suggests that we might be too consumed by old power models of sex, money and colonialism to survive a brave new world that could supplant us.

Deeper, this is the work of a writer obsessed with facts — in awe of them, really — and yet, someone also convinced that facts will only get us part of the way there. (Among the things you learn when you give yourself over to Pynchon: The guy wanted to study math at Berkeley but was rejected; he also held a day job at Boeing writing about weapons systems.) You don't have to be a tech head to love these books; let the details flow over you and work your way in when you can. Actually, Pynchon's alarmingly confident debut novel, 1963's V., is a great way into Gravity's Rainbow. It gets you accustomed to his style, while teaching you more than you ever wanted to know about nose jobs. 

Right of way: The death of the counterculture, stranger days ahead
Above and beyond the pop songs and the dense thickets of technical talk, Pynchon does a consistently elegant job of situating his plots (such as they are) at the fissures of a changing world. Think of Paul Thomas Anderson's The Master — those scenes where Joaquin Phoenix's ex-Navy drifter can't fit into a post-WWII department store because a switch has gone off inside him; he's too rambunctious, too much of a fuck-up. This is a spin on Pynchon's discharged sailor Benny Profane, the hero of his 1963 novel V., and whose gang, the Whole Sick Crew, might be likened to Philip Seymour Hoffman's clan of spacey hangers-on, searching for meaning at a time when the old answers don't work anymore. The mysterious "V" — perhaps an alluring woman, perhaps a rat — at the heart of Pynchon's debut effort leads his characters into Manhattan's sewers and deep existential doubt. And still they go, untethered by square society.

Pynchon's books happen at moments of profound cultural and sociopolitical change, only half-understood by the players. Vineland, published in 1990 after 17 years of near-silence from the author, takes place in California during the rising Reagan Revolution. It's 1984 and Pynchon's gentle dope smokers are decidedly on the outs during Nancy's War on Drugs. Meanwhile, the shopping malls lure the kids. Inherent Vice has a simpler version of this set-up, pitched in 1970 at a post-Manson moment when Nixonite cops do battle with hippies who are suddenly out of fashion. Not all of his books hinge on obvious moments of transition; sometimes, he casts too wide a net. If you push your way through Pynchon's 2006 door-stopper Against the Day, spanning globally over three decades at the turn of the 20th century, please tell us if you figure anything out.

But he's never lost his edge — at least not yet. Pynchon continue to tease out grand importance from history's pivot points, at which the machinery of technology and culture swirls to an ulterior end. You can see this as recently as last year's Bleeding Edge, a fiercely funny 2001-set New York City tale that pits the ominous bloom of the Internet Age against the real-world events of one terrible Tuesday. (And if you think that sounds crass, back off: Pynchon may be the one American author who’s earned the right to tackle it.) Already the novel's been called unfilmable, but if we've learned anything from Anderson's Inherent Vice, that term's going out of style. You'll breeze through it, be reminded of The Crying of Lot 49's Oedipa Mass with its brassy fraud-examiner heroine, Maxine, and start salivating for the next book. They can't come soon enough: We Pynchonites need to wrap our heads around something truly heady, we need to ache at the stretching and smile at the widening. Let it be a thick one.