Difficult, Dated, Frustrating, Prophetic: Teaching Thomas Pynchon

April 3, 2015 | 3 books mentioned 18 6 min read

In a 1978 debate with William Gass at the University of Cincinnati, John Gardner said the fiction of Anthony Trollope is rarely taught “because it’s all clear.” In contrast, “every line of Thomas Pynchon you can explain because nothing is clear.” The result: “the academy ends up accidentally selecting books the student may need help with. They may be a couple of the greatest books in all history and 20 of the worst, but there’s something to say about them.” Gardner warned that “The sophisticated reader may not remember how to read: he may not understand why it’s nice that Jack in the Beanstalk steals those things from the giant.”

covercovercoverNeither Gardner nor any other single critic is the final word on what belongs in a classroom, but I admit some deference to his voice. His books The Art of Fiction and On Becoming a Novelist were influential to me as a young writer, and his playful debate with Gass has been invaluable in showing my students the tension within American fiction during the late ’70s. Yet Gardner’s polemical On Moral Fiction soured me a bit. He opted for a bullhorn where a flute might have been more appropriate. Gardner’s critical shouting was a show, a way to carve out a niche for his own literary identity. In a later interview with The New Orleans Review, Gardner is more measured: he calls Pynchon “a brilliant man, but his theory of what fiction ought to do is diametrically opposed to mine, and while I think he’s wonderful and ought to be read — besides which it’s a pleasure — I don’t want anybody confusing him with the great artists of our time. He’s a great stunt-man.”

coverI end my senior AP Literature course with the stunt man. The first text I give my students is Gass and Gardner’s debate; we finish with The Crying of Lot 49 by Pynchon. Between Gardner and Pynchon, the students read a significant amount of poetry, as well as novels by Graham Greene, Toni Morrison, Don DeLillo, William Faulkner, and plays by Eugène Ionesco and Jean-Paul Sartre. I end with Pynchon because his fiction is difficult, dated, and frustrating: exactly what my students need to read before they go to college.

Difficult, dated, and frustrating requires some explanation.

Pynchon is difficult because of his syntax. Consider the first sentence of The Crying of Lot 49: “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.” Pynchon’s sentences are labyrinthine and recursive: full of noise. As his sentences become paragraphs, and his paragraphs span pages, the novel becomes a whirlwind of paranoia; a test of a reader’s endurance and patience.

Pynchon is dated. The novel’s first chapter contains references to The Shadow and Lamont Cranston, parodies of television legal dramas and ’60s local radio station DJs, and Timothy Leary’s consciousness-bending theories. The next chapter introduces Miles, a manager of a local motel, who is “maybe 16 with a Beatle haircut and a lapelless, cuffless, one-button mohair suit,” whose band is called “The Paranoids.”

covercoverPynchon is frustrating. Although my students read difficult books, ranging from Morrison’s layered representation of trauma in Beloved to DeLillo’s absurd mash-up of linguistics and football in End Zone, each previous novel builds toward a resolution. Pynchon tricks, trips, and nearly pummels the reader with herrings of every color. Oedipa’s search is continually diverted with distractions, and that’s before she learns of The Tristero or Trystero, the multinational, historical conspiracy that has culminated in an underground postal system, W.A.S.T.E.

Pynchon has written six novels since The Crying of Lot 49, so why teach this early book that Pynchon himself said was a work “in which I seem to have forgotten most of what I thought I’d learned up till then?” Because I know that students, pushed by a teacher who believes in them, will rise to the difficulty of the material presented.

We read Pynchon for the same reasons that others might not.

Pynchon’s difficult syntax forces students to juggle two methods of reading: reading for language, and reading for content. That previously quoted first sentence has a lot of noise, but it is not cacophonic. Pynchon’s convoluted syntax mirrors Oedipa’s increasingly chaotic world. His sentences force students to rethink their assumptions about the purposes of not only traditional prose, but also experimental language. I do not intend Pynchon’s work to convert them to more postmodern interests in literature; rather, Pynchon’s fiction is like a literary workout that forces them to build from the ground up as readers. When students read easier works of literature, they might become deluded into thinking that all language is employed in the service of clear communication. Pynchon’s paradoxes make them return to other, non-literary texts with a bit more skepticism and independent thinking.

Although Pynchon’s references and comedic timing within The Crying of Lot 49 might feel dated, the novel helps students understand mid-’60s American fiction, particularly work from the West Coast. One might update the curiously self-deprecating band The Paranoids for our present as Big Data, a Brooklyn-based act founded by Harvard graduate Alan Wilkis. In a recent interview with NPR, he spoke about his “paranoid electronic pop project,” and how “I wouldn’t be here if it weren’t for the Internet.” Big Data’s great debut album, 2.0, leads with “The Business of Emotion,” a send-up of the “Facebook mood experiments:” “Feel good, make you feel good / I’m looking for emotion so I know just what to show you.” Students realize that, more and more, they are becoming Oedipa, buried in data: “They knew her pressure points, and the ganglia of her optimism, and one by one, pinch by precision pinch, they were immobilizing her.”

Finally, student frustration with Pynchon evolves into curiosity. Rather than becoming angry at Pynchon’s lack of linear progression and profluence, students are often intrigued by his parlor tricks. For years they have been taught to unearth and discover meaning in texts — English educators love to use manual labor metaphors, but don’t always want to get their hands dirty — yet The Crying of Lot 49 makes students consider what happens when a work of art might not have any traditional secrets to reveal. The movement toward skills-based education in the humanities has also created an effort-return mentality: the expectation that a text can, or should, be distilled into a single sentence. Don’t we want students who know how to handle messes?

There are many other difficult novels that could fit the aforementioned criteria. What is special about Pynchon and The Crying of Lot 49?

covercovercoverPublished in 1965, Pynchon’s novel fits nicely within the decade of media theorist and “electronic prophet” Marshall McLuhan’s essential works: The Gutenberg Galaxy (1962), Understanding Media (1964), and The Medium is the Massage (1967). As Mark Greif notes in The Age of the Crisis of Man, his excellent consideration of American fiction between 1933 and 1973, “Pynchon [puts] a TV set in every room of his fiction — often to drive the action.” McLuhan’s “electric light” illuminates Pynchon’s fiction.

Oedipa is the protagonist that McLuhan might dream of, a woman thrust into an electronic world she did not create but is forced to understand. Early in the novel, Oedipa and Metzger, her part-time lover, part-time legal mentor, visit The Scope, a nightclub on the outskirts of Los Angeles with “a strictly electronic music policy.” A “hip graybeard” explains “They put it on the tape, here, live, fella. We’ve got a whole back room full of your audio oscillators, gunshot machines, contact mikes, everything man.” As Oedipa drives through San Narciso on a Sunday, “She looked down a slope, needing to squint for the sunlight, onto a vast sprawl of houses which had grown up all together, like a well-tended crop, from the dull brown earth; and she thought of the time she’d opened a transistor radio to replace a battery and seen her first printed circuit.” Oedipa’s world is wholly electronic; in fact, considering Pynchon’s sensibility as a jester-Catholic, holy electronic.

My students watch McLuhan’s 1976 appearance on The Today Show and are entertained by his dissection of the presidential debate between Gerald Ford and Jimmy Carter. “I never saw a more atrocious misuse of the TV medium,” he quips, and calls the moment when the sound cut during the debate a “rebellion of the medium against the bloody message.” If the bloody message is linear, progressive, and climactic storytelling, Pynchon’s novel is rebellion through performance. Greif notes that “‘Man’ as a being and a concept is put into jeopardy for Pynchon, not first by high-technological machines or weapons but by the use of ordinary materials and the creation of mundane objects — the changing status of the parts of men, and the insertion of inanimate things into their bodies and daily habits.” I don’t want students to smash their iPhones, but I do want them to think twice about what type of data they offer their devices.

At its worst, Pynchon’s prose is a beautiful failure. At its best, Pynchon’s prose is revelatory. I agree with Greif that, in the end, The Crying of Lot 49 and Pynchon’s canon as a whole are concerned with data: “whether remains are transmitted beyond each individual communication, buried in the material facts of the founding of the system of communication, and whether this residue may shadow and smudge the prospect of those who join such a system, without them even knowing it.” Not a bad lesson for students to learn, somewhere between thinking of giants, beanstalks, and other noise.

is a contributing editor for The Millions. He is the culture editor for Image Journal, and a contributor to the Catholic Herald (UK). He has written for Rolling Stone, GQ, The Paris Review, The Atlantic, Esquire, and the Kenyon Review. He is the author of Longing for an Absent God and Wild Belief. Follow him at @nickripatrazone and find more of his writing at nickripatrazone.com.


  1. There is a reason that Lot 49 is dated – it’s supposed to be. It takes place at a particular period in American history. Is Anna Karenina dated because it takes place in the 19th century? Saying that Pynchon is dated and difficult to teach is, I’m sorry, just plain laziness.

  2. Why is it laziness? He isn’t saying Pynchon isn’t worth teaching because of that — I gather he thinks those elements can be used to make the teaching of Pynchon rewarding.

  3. Here’s the quote:

    “I end with Pynchon because his fiction is difficult, dated, and frustrating.”

    I agree that Lot 49 is difficult and frustrating, but not dated.

  4. This is the key from this terrific essay:

    “When students read easier works of literature, they might become deluded into thinking that all language is employed in the service of clear communication.”

    I’d go further: the choice to be simple (whatever that may be) is a choice that reflects a view of the world, a philosophical approach or something less apparent than the “message” being “communicated”. John Gardner, by writing the way he did, expressed his philosophy as surely as Pynchon expressed his. The idea that literature is good for you because it teaches you something is an argument against thought and experience.

    Jack M: he clearly explains what he means by dated. He is also describing the reactions of his high school students. As the father of a very intelligent, well-read 16 year old, I can assure you that even he would stumble over “Tupperware party” in the first line. The book is full of similar references to contemporary ideas and brands and pop references. They are inevitably dated, but you seem to be attaching a deeper meaning to “dated” than the writer intends, as if he was saying the post-modern project itself is dated. He may or may not think so, but he certainly doesn’t say so in here.

    Frankly, if you are passionate about Pynchon, you should be celebrating that he teaches him in high school. I can assure you, that is not the case in every school.

  5. The other consideration here is how Pynchon influenced later authors many of these students probably have heard of and read – people like David Foster Wallace, Christopher Wunderlee, Zadie Smith, Neal Stephenson, TC Boyle, and others.

    By placing a writer like Pynchon into context within the evolution of post-modern literature, it can illuminate for students how innovations in form, style, syntax, etc. foster a living art form.

  6. I agree with other commenters that the word “dated” here is pejorative and misleading. Each Pynchon novel is not only set in but saturated with its time period. By this author’s lights, Mason & Dixon was already “dated” on the day it was published, and in fact for 200 years before it was written, since it uses language, allusions, and genre tropes (like the captivity narrative) that had long since faded from common use and memory. Saying the work is “dated” makes it sound like Pynchon is an unwitting product of his time, when in fact he has the rare gift of being able to see even the decades in which he lives and writes through the defamiliarizing lens of history.

  7. Of course Pynchon is dated, he dates himself. He takes pains to make the most specific references that most people won’t get unless you come from his specific background. And some of the things he says about race do NOT play well today. So it teaches students how to read a dated work.

  8. Mason & Dixon is also “dated” because it is festooned with references to things that are contemporary to 1997, like that old salt Patrick O’Brien.

  9. Is it a criticism to be dated before the usual time span of standard dating, like, say,” Washington Square”? Or is it a criticism that Pynchon is a Pop writer as if he were a Harold Robbins? And by the way, if Artists take the everyday and intensify it and transform it, then a professional stuntman is an Artist in true esthetic form.

  10. “The movement toward skills-based education in the humanities has also created an effort-return mentality: the expectation that a text can, or should, be distilled into a single sentence. Don’t we want students who know how to handle messes?”

  11. To really see the comments explode, The Millions should have included a reference in the essay to Jonathan Franzen calling Gaddis “Mr Difficult.” This comment should help lol

  12. Jack M, 7:28, April 3: “There is a reason that Lot 49 is dated – it’s supposed to be.”

    Jack M, 10:37, April 3: “I agree that Lot 49 is difficult and frustrating, but not dated.”

    Which is it, guy? Is it dated or not?

  13. Benn at 3:56 pm on April 3, 2015 had the best comment of all time.

    We should all take a moment to appreciate the true genius behind it.

  14. “I know that students, pushed by a teacher who believes in them, will rise to the difficulty of the material presented.”
    Wow, you’re gonna have a rough time when you realize how little your students care, how deeply rooted their apathy, how shorn of anything but a desire for convenience and pleasure and immediate gratification. The vast majority of American students, no matter how much you “care,” are unsavable. They’ve been ruined by substandard schooling, parenting and genetics. They aren’t rising, they’re just duping you, man, they’re appeasers, people pleasers and connivers. Keep fighting the good fight though, Mr. Holland. There’s that small percentage you’ll “reach,” and maybe that makes it all worth it. I’m admittedly torn between derision and grudging respect at the naivete of the statement above.
    On Pynchon, you’re pretty much on the mark and I’ve liked a lot of your other work on this site and elsewhere, but man, the naivete and willful ignorance that one amazingly “American” sentence reveals. You definitely vote for major parties (almost certainly democrat) and think it matters.

  15. One summer afternoon, Mr. Nick Ripatrazone came home from a faculty party whose host had put perhaps too much presumption in the punch to find that he, Nick, had named himself pedagogue, or he supposed exasperated demagogue, of the work of one Thomas Pynchon, a New York literary paragon who had once cut two million words in his spare time but still had a vocabulary output numerous and tangled enough to make the job of relegating it to simplistic readings more than honorary.”

  16. “We read Pynchon for the same reasons that others might not.”

    These are very different times from the times during which Pynchon was encouraged to write as he did. We need to own up to this massive shift in… cognition? Data processing? We’re strapped to a sled on an exponential curve of high-tech change and wondering why things from 50 years (or six months) ago seem a little… strange to us.

    A generation ago, a generation trained by TELEVISION, to “read” narratives in a way native to TELEVISION, interacted with the Literature in a (semi-estranged) way peculiar to itself… and that was shift enough (after c. 500 years of things changing very, very slowly). And now THE INTERNET is changing even that change.

    LOGOSAPIENS are dying off. And TELESAPIENS are soon to be dying off. Long live PHOTOSAPIENS. Many of whom will know Mr. Pynchon only as a minor Simpsons character beloved of their grandparents.

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