Thomas Pynchon, the great American novelist, may be best known for being invisible. (Although he did do a voiceover on an episode of The Simpsons). Who is he? Where does he live? He is also known for being Too Damn Difficult to read. In celebration of Pynchon’s 83rd birthday, Gary Lippman offers eight reasons why you should give him a try.

I missed Thomas Pynchon’s birthday this year.  In the past I’ve usually managed to catch the date as it’s come around and silently wish glad tidings to one of my favorite contemporary novelists, but lately I’ve been blaming the Covid-19 pandemic for everything, so I might as well also blame it for my missing Pynchon’s 83rd. The time is always ripe, though, to celebrate this most private, hence enigmatic, of American artists. With our global crisis still more or less in effect, the time is ripe, too, for new readers to get Pynchonized. And ripeness, as Shakespeare “always sez” (to use a typical Pynchonism), is all.

Rare photo of Thomas Pynchon from his High School Yearbook.

Not that the postmodernist master’s reputation as Too Damn Difficult is likely to evaporate.  According to the standard kvetch about his work, his prose is overly dense; his subjects, ranging from physics to postal delivery, are too arcane; and the print is too small on too many pages, with one novel breaking the thousand-page mark. In this age of diminished attention spans, who’s got the patience or dedication for that?

Points well taken.

Fortunately, though, some readers do keep enjoying the work of Neil Stephenson, William Gibson and the late David Foster Wallace, who are obvious heirs to Pynchon publishing work that’s just as challenging as his. (And note, please that Pynchon doesn’t do footnotes, unlike the plethora of them in Foster’s Infinite Jest.)

Also fortunate is the fact that the most recent of Pynchon’s novels, Bleeding Edge (2013) is Pynchon at his reader-friendliest and most engaging—an excellent place for newbies to start. But in case you need further convincing, here are eight reasons to give Pynchon a chance.


Mason & Dixon (published 1997) recounts the shared, and separate, accomplishments of the 18th-century British astronomers who surveyed that famous American “Line.”  Although the novel followed John Barth’s Sot-Weed Factor as a parody of colonial literature, it’s wilder and woollier in every way, not least in its rendering of old-time diction.

Against The Day (2003) begins at Chicago’s World Fair of 1893 and spends time in the American West before sailing over to Europe, where it wanders as far east as Russia and then concludes Stateside in the 20s.   V. (1963), Pynchon’s first novel, ranges even farther—from Europe in the late 19th century to America in the mid-20th century.

Gravity’s Rainbow (1973), regarded as the Big Kahuna of the author’s canon—far more readers claim to respect it than have finished, or even opened, it—is the author’s World War Two opus, set mainly in Western Europe during wartime, yet rocketing like the book’s V-2 missiles around the world and flashing backwards, forwards, and sideways through time, just as all his novels do.

Both The Crying Of Lot 49 and Inherent Vice confront the ‘60s in Southern California and its environs. The former was published in 1966, smack dab in the middle of that golden age of creative ferment, while the latter came out decades later, in 2009, as a mournful elegy for the decade.   Also redolent with ‘60s nostalgia is Vineland. Published in 1989 but set in the Orwellian—make that Reaganian—annus horribilis of 1984, Vineland depicts a Northern California populated by aging hippies and their progeny as well as the hippies’ enemies and ex-comrades. Oh, and a shy Japanese insurance adjuster. Plus a sexy blond ninja. Who hook up.

Which is what I mean by “history with a twist.”

Facts, however scrupulously researched, are merely the jumping-off point in Pynchon’s work.   For the same price, readers also get served philosophical reveries, bizarre allusions, protracted flights of fancy, outrageous metaphors galore—and scene after scene after scene of playful inventiveness.

Take, for an infamous example, the “Byron the Bulb” tale interpolated into Gravity’s Rainbow. Toward the end of the book, the author mentions a nondescript lightbulb while setting a scene, then launches into a ten-page biography of the thing. Turns out this lightbulb is sentient—and its situation, we realize, meaningfully parallels the plight of the book’s human protagonist.

Pynchon, in short, is a consummate storyteller, very much in the “big-picture” novelistic tradition. Like Don Quixote, Tom Jones, Bleak House, War And Peace, Ulysses—and Gunter Grass’ titanic Tin Drum (not read nearly enough anymore)—Pynchon’s are “world-books,” which seek to cram as much of life’s stuff, its possibilities and impossibilities, as they can between their covers.

Certainly the author has crammed everything but the kitchen sink into Bleeding Edge. Set in 2001 in Manhattan, it’s Pynchon’s Internet book, his 9/11 book, his 21st-Century book, his most “ethnic” and female-centric book—but primarily it’s his New York book, a worried and weary yet likewise joyous paean to the city, especially the Upper West Side, where the scribe has reportedly lived for many years now.  From eerie faces glimpsed on subway trains to waiters “whose credits include a couple of Sopranos episodes,” from Greek diners uptown to Ukrainian diners downtown, from a “Geeks Cotillion” in Soho and cursed Dakota-like apartment buildings to the decidedly less-sexy Javits Center, Port Authority, and newly Disneyfied “Forty Deuce,” Bleeding Edge aims to be as exhaustive, exhausting, and exhilarating as good old “Fun City” itself.

Gravity’s Rainbow -First US Edition.


Mindless Pleasures” was supposedly a working title for Gravity’s Rainbow (and rightly dispensed with). The term also describes another appealing aspect of Pynchon’s work:  the regular appearances of sex, drugs, rock’n’roll, and other aspects of pop culture.   Pynchon being Pynchon, these mindless pleasures are often, shall we say, distinctive:  orgies and coprophilia (look it up) in the sex category, made-up drugs both licit and illicit, and songs (not just rock’n’roll, either) that characters burst into at unexpected moments. (Will some composer kindly put Pynchon’s lyrics to music? Especially the one about Amy Fisher?)   (If you don’t remember Amy, consider yourself blessed.)

As for Pynchon’s pop culture content, it’s ubiquitous, not just in the postwar novels (where “the Tube” and its kitschy offerings clearly stir up both love and hate in the author), but in the historical texts as well. My favorite Pynchonisms in this realm are anachronisms, beaming a somewhat contemporary pop reference incongruously back in time: the ‘20s-era Teutonic behavioral scientist with a ‘60s Black Power-slang name (“Jamf” equals J-ive  A-ss  M-other  F-ucker) and the fin de siecle Arab who mispronounces his R’s as W’s and whose own moniker resembles that of a certain later cartoon character:  Al Mar-Faud.

Truth be told, Bleeding Edge is a bit light on the drugs and the sex (though a shoe fetishist gets a foot-job).  But music is front-and-center, with the rock here getting schooled by pop and merengue and hip-hop, in particular during a hilarious karaoke scene. What’s more, pop culture referents ripple across nearly every page, including someone receiving a longed-for Jennifer Aniston hairdo.

 Does Pynchon debase his artistic seriousness with such nonsense?   Some readers think so.   My own view is that pleasures, even mindless ones, have their place; one man’s sophomoric schtick is another man’s “carnivalesque .”  Anyway, as a wise ancient Roman said, “Nothing human is alien to me,” and no world-book worth its salt would exclude the lowbrow just to focus on the middle and the high.

Bleeding Edge. First US Hardcover.


A profound, and profoundly moral, view of social existence informs Pynchon’s books.   It can be summarized—over-simplified, perhaps—as “powerful people and institutions will always conspire for their own benefit at the expense of the powerless, but the powerless, in their own anarchic yet humane, even noble fashion, will always fight back.” Thus, squaring off against the Golden Fangs of the world will be the Tristeros, or Counterforces, or unnamed clusters of individuals whose struggle might, just might, end with a small but significant success.

Early on in Bleeding Edge, for instance, Maxine Tarnow, a small-time (indeed, decertified) “fraud investigator” begins delving into the doings of a nefarious dot-com called “hashslingrz.”   The CEO there, one Gabriel Ice, has risen from the ashes of the recent tech-bubble’s bursting to cut heinous deals with the worst of the U.S. intelligence machine as well as, maybe, Al Qaeda.  Other potential suspects in the inevitable unsolved murder include a pair of Russian videogame-gaga thugs; a Montreal sharpie; an aging female activist with website and axes to grind; a WASP princess who wants to feel Jewish; a goomba prince who wants to be WASPish; a man with an astoundingly acute sense of smell (one of his compatriots predicts 9/11 entirely by scent); and too many coders and hackers to mention.

The paranoia gliding like vapor through each Pynchon text is less leitmotif than overarching theme, his surest source of comedy and tragedy and meaning, since a paranoid person can spot connections out there that the rest of us miss or ignore.  It’s a fraught sense of connection, true, but probably better than its alternative, the extreme opposite of paranoia, which is to find that nothing in this world connects with anything else, and thus everything lies in pieces, fragments, shards. Sort of like the broken vessels of light in the medieval Jewish mystic system of Kabbalah. And broken light-vessels might be easier for the remorseless power-mad like Gabriel Ice to scoop up and bogart.

Kabbalah, by the way, is a semi-recurring reference for Pynchon, one of the countless thought-vehicles he deploys in his narratives. Science and the occult are given equal time; both are treated as valid guides for us to comprehend our origin and destiny. So are legends and archetypes, folk wisdom, and crackpot notions. Everyone, so to speak, gets invited to the party, mathematicians and ghosts alike. Even when that party is a funeral.

Or a chase scene.

Or, in Bleeding Edge, Maxine’s night-journey by boat to “toxicity central,” a vast garbage dump near Staten Island called Island of Meadows.


Sophisticated comic wordplay and situations abound in Pynchon’s novels, of course, but the author, in line with his jones for mindless pleasures, is fond of laying down vulgar jokes, ridiculous puns, preposterous acronyms, pastiched syntax, and goofy names, including, to cite those of a few Pynch-protagonists, Benny Profane, Herbert Stencil, Oedipa Maas, Zoyd Wheeler, Wicks Cherrycoke, Webb Traverse, and Doc Sportella.   A buffoonish naval officer named Pig Bodine turns up in multiple books, when it isn’t one of Pig’s ancestors instead.   And Bleeding Edge has its share of saucy new winners.  A strip club called Joie de Beavre and an East Indian proctologist named Pokemon are the most obvious laugh-getters, but I’m partial to a threesome-addled sleaze who goes by the name of Viv Epperdew.

Of course, there’s usually something deeper to the name-game than mere kookiness. “Tyrone Slothrop” in Gravity’s Rainbow, for example, contains the word “sloth,” a key to his nature, as well as an anagram for “entropy,” a frequent concept in Pynchon’s early fiction and a clue to Slothrop’s unusual fate.  Since a Pynchon novel typically boasts a cast of hundreds, the author has by now coined enough names to fill a published lexicon of the monikers, complete with their derivations.  You can file that tome, Pynchon Character Names: A Dictionary by Patrick Hurley, alongside the countless reader’s guides, online wikis, scholarly treatises, and fanzines that elucidate each novel, line by line by line.

But back to the humor. Much of it in Bleeding Edge derives from Maxine’s being a plotz-prone Jewish woman. While she’s not Pynchon’s only female protagonist, she is the novelist’s first major Jewish character, and throughout the new novel, her Yiddishisms and Yiddishkeit sensibility feel so authentic, and are so authentically funny, that you might think Pynchon’s family name got changed at Ellis Island from the original “Pynchonovsky.”   Or “Pynchonowitz?”

First US Hardcover


Sometimes forgotten in the hubbub about Pynchon’s other literary virtues is the fact that the man can write some truly poignant scenes of longing, love, and loss. The relationship between parents and children tend to receive particularly empathetic treatment. In my opinion, the Rainbow scenes with Franz Pokler and his “false” daughter set the gold standard for pure heartbreak, but Bleeding Edge features the most whimsical and comprehensive rendering of parenthood in all of Pynchon. Maxine’s interactions with her mother and father are sweet, to be sure, but it’s her love for two preadolescent boys that’s paramount.

On September 11th (or “11 September,” as Pynchon keeps referring to it) Maxine’s husband Horst goes missing. His office is toward the top of the World Trade Center, yet Maxine reassures her young sons Ziggy and Otis that there’s no need to worry.

They’re not buying it. Of course they’re not.   But they both nod anyway and just get on with it.  A class act, these two.  She holds their hands, one on either side, all the way home, and though this sort of thing belongs to their childhood and generally annoys them, today they let her.”


Without a doubt, Pynchon is a linguistic wizard, with a grand array of voices at his command. Whether he’s writing formally or casually—describing Siberia in undulatingly poetic lines, say, or wisecracking bluntly—his language is pungent and dazzling.

9/11 prompts one of my favorite passages in Bleeding Edge. A few months into 2002, Maxine and a new friend stand on the Brooklyn Bridge, “as close to free as the city ever allows you to be, between conditions, an edged wind off the harbor announcing something dark now hovering out over Jersey, not the night, not yet, something else, on the way in, being drawn as if by the vacuum in real-estate history where the Trade Center used to stand, bringing optical tricks, a sorrowful light.”

It was never the Statue of Liberty…,” Maxine goes on to remark, “never a Beloved American Landmark, but it was pure geometry. Points for that. And then they blew it to pixels.”


Yes, flaws—not all of us Pynchonophiles are entirely uncritical.   Those frothily silly names, for instance, suggest a problem with Pynchon’s work—a playing-fast-and-loose with characterization. There’s no frivolity about Pynchon’s protagonists, who are pretty fully realized, but his plethora of less important characters, cartoonish types that they often are, may fail to win readers’ belief, much less their sympathy.  What’s worse, the profusion of the “flat” characters can bewilder you as they zing around one another like souped-up chess figures, or else pop in and out of narrative existence like quantum particles.  There is simply too much happening to too many characters for the books not to, well, sprawl.  And, with the exception of the tightly woven Crying Of Lot 49, momentum in Pynchon’s novels doesn’t build to a climax, at least not any conventional kind.  Storylines tend to break down, decay, come undone.

The character issue seems more prominent in the recent books, and especially with villains. In Bleeding Edge, Maxine has a sordid, self-debasing affair with Nicholas Windust, a cruel government assassin.   Although her feelings about Windust and about her “sleeping with the enemy” are expressed by Pynchon with fluency and feeling—the ex-wife of the assassin even shows up to bond with Maxine and reveal her own complex feelings—Windust never strikes you as multi-dimensional enough to match Maxine, or that ex, in any sense of vibrancy, of realness.

One could respond to the above critique by arguing that the flat characters and diffuse plots are intended—part of Pynchon’s program. That is, he wants to thwart readerly expectations and desires, to parodically play with stereotypes of plot and character not unlike how Fielding and Dickens did, to deploy our emotions for his “rounded” people while modelling the flat ones for different aesthetic purposes.   Ditto their storylines.

My advice is to forget such nitpicky academic matters.   Just sit back and enjoy the show. Use the reader’s aids for assistance, skim the vexing passages, and limit yourself, at least at first, to Bleeding Edge, Inherent Vice, and Vineland, the most immediate of the novels. Or begin, perhaps, with Lot 49, his shortest, most artistically unified book. It’s not my favorite Pynchon, but it’s the one I find closest to perfect on standard literary grounds.


That business of Maxine transgressively “sleeping with the enemy”—it’s not the first time in a Pynchon book that a more-or-less virtuous female has given herself to a man she knows to be more-or-less heinous. What does it say about Pynchon that he returns to this specific guilt-and-pleasure-charged scenario so often in his work?  What do any of his other frequently-returned-to situations and concerns tell us about the person who fashioned them?

He obviously won’t tell us himself.  By all accounts, Pynchon guards his privacy supremely well. The publicly available photographs of Pynchon are few and from his youth (with one or two craven paparazzi-style exceptions). And the hard facts known about him are even fewer, or seem to be:  Born in ’37 to a centuries-old WASP family (forget that earlier Ellis Island crack of mine—Hawthorne wrote about them), Pynchon grew up in Oyster Bay, Long Island and then attended college at Cornell, where he befriended the future novelist/folksinger Richard Farina. Afterward came a stint as a technical writer at Boeing, friendships with other writers and artists while Pynchon lived in Manhattan Beach, Calif. (the Gordita Beach of Inherent Vice) and Northern California (the Vineland of Vineland). Finally, there was Manhattan, where he married his literary agent and became a father. Between Gravity’s Rainbow and Vineland was a sixteen-year gap between novels, but his publication rate has increased during the past two decades.

Aside from his nine books, Pynchon has put out essays over the years on such subjects as the Watts riots, sloth, and Luddites; book reviews and blurbs; introductions to 1984 as well as fiction by his friends (Farina, Donald Barthelme, and Jim Dodge, whose novel Stone Junction is a must-read); liner notes to record albums (Spike Jones and an early-90s indie-rock band called Lotion), plus amusing brief voiceovers for The Simpsons and for a publicity video.

That’s a lot of informational footprints, you’d think—though except for a long essay at the start of his early story collection Slow Learner, Pynchon has obscured and lacuna’ed the story of himself as much as he’s revealed.

The best portrait of the author is Boris Kachka’s 2013 vulture.com essay “On The Thomas Pynchon Trail.”   Brief as it (relatively) is, Kachka’s piece is the closest thing to a biography we have. As for interviews with Pynchon, forget it—unless you look to a most surprising locale:  the autobiography of Clarence Clemons, the much-loved late saxophonist in Bruce Springsteen’s E Street Band. “My Day Hanging Out In San Francisco With My Old Buddy Thomas Pynchon” could be the title of this delightful chapter from Big Man. The veracity is iffy—Clemons and his co-author Don Reo say it might be a “tall tale”— yet the disclosures and details about Pynchon ring true.

In the Clemons book, the novelist even coyly explains his quest for privacy (leaving out his own likely personal tendency toward paranoia). He says he believes his books should, and do, speak for themselves.  In other words, the old “Trust the art, not the artist” business!

Which brings us back to the work themselves.  Despite the books’ fictional nature, these remain the primary source for understanding Pynchon—his inner life, his obsessions, his ideals.   Most readers, just cruising for literary kicks, won’t be impelled to dig beneath the surface of the texts and chase clues about their shadowy creator.   For Pynchonophiles, however, it’s a fascinating game to gather together the myriad puzzle-pieces and assemble them into a portrait of the Pynch, with each phile’s portrait subtly, or not so subtly, different from the others. Bear in mind, too, that all Pynchonophiles started out as casual readers who simply got hooked.

In other words—let’s evoke some closing paranoia here—you could be next.