Three potential starting points for reading Thomas Pynchon


Today is Pynchon in Public Day, so here are three books that I think may make good entry points for those interested in, but perhaps unnecessarily daunted by, Thomas Pynchon. My intuition is that many readers’ first experiences reading Pynchon may have been like mine: I read The Crying of Lot 49 as a college assignment, found it bewildering and baffling, and despite understanding almost none of it, I then attempted Gravity’s Rainbow (the key word is attempted (failed will also do in a pinch)).

Many readers start with The Crying of Lot 49 because it’s short. While I like the novel (I wrote about it here), it’s also extraordinarily dense, a box so crammed with jokes and japes that some fail to spring out at full force. Lot 49 is a much better reading experience after you’ve read more of Pynchon.

Lots of readers new to Pynchon plunge into Gravity’s Rainbow, probably because it’s famous. I love love love Gravity’s Rainbow, but along with Mason & Dixon (which may be my favorite Pynchon novel), I do not think it is a good starting place for Pynchon. Gravity’s Rainbow is a rich, ringing vortex, a seven-hundred-and-something pager that almost necessitates that its reader immediately reread it. Gravity’s Rainbow is a very funny and very tragic book, and I think it is the work of genius that its reputation suggests—but it’s also one of the few books I can think of that get put on lists of Big Difficult Novels that is, actually, Difficult.

So here are my suggestions for starting places for Pynchon.


Against the Day, 2006.

Okay. So maybe you’re saying, Waitisn’t that one, like, really long? Reader, you’re correct. At 1,085 pages Against the Day is Pynchon’s longest novel to date. But it’s also one of his most accessible, and, most importantly, it offers a condensation of Pynchon’s Big Ideas and Big Themes. (I wrote a list of 101 possible descriptors for Against the Day, if you’re interested in a short take; I also riffed on the book at some length in a series of posts).


V., 1963.

V. is Thomas Pynchon’s first novel. It’s also the first Pynchon novel I read and loved and (possibly) understood. Like Against the DayV. lays out many of the themes and styles (and even a character or two) that appear elsewhere Pynchon’s oeuvre. In a loose sense, V. feels like a dress rehearsal for Gravity’s Rainbow. Oh, it’s also pretty discursive—in fact, you can read chunks of it almost as short stories. In fact, here’s a good way to break into Pynchon: Get V., and read Ch. 9–it stands on its own as a long short story, the tale of Kurt Mondaugen—and colonialism, siege paranoia, dark dread, etc.


Inherent Vice, 2009.

I’ve heard Inherent Vice dismissed as “Pynchon lite,” which may be true—I’ve read the book twice now and if its shaggy threads connect, I can’t see it (unlike, say, Gravity’s Rainbow, which resolves like a complicated math problem). Still, Inherent Vice makes a nice gateway drug to Pynchon—it’s funny and loose, and even though it rambles through an enormous cast of characters and settings, it’s ultimately far, far more contained than sprawling novels like Mason & Dixon and Gravity’s Rainbow. Paul Thomas Anderson’s film adaptation also makes an interesting visual counterpart to the novel—which it somehow simultaneously condenses and expands. Inherent Vice—the novel—also seems to me a kind of bookend or sequel to The Crying of Lot 49. (I wrote a bit about that here).

Last thought: Ignore my suggestions. Pick any novel that interests you by Pynchon and dive in. Don’t get too frustrated if you’re not sure what’s going on. A lot of the time, that’s the point of it all. Enjoy it.

[Ed. note–Biblioklept ran a version of this post on 8 May 2016].

7 thoughts on “Three potential starting points for reading Thomas Pynchon”

  1. Reblogged this on Progressive Geographies and commented:
    Yesterday was Pynchon’s 80th birthday. I’ve read all his books, some a few times, except Against the Day. I started it, got about 200 pages in, didn’t take it with me on a trip and never picked it up again. I should go back to it. All his books are worth the trouble, but Mason & Dixon is an especially wonderful book for anyone interested in geography…


  2. Great post. If any writer needs a “How to start with…” guide about them it’s Pynchon, but mostly to warn people not to start with Gravity’s Rainbow! It’s a little much for the uninitiated.


  3. Lovely post! Thanks for your insights. I’ve been reading Pynchon on weekends (a couple hours each Saturday and Sunday morning, when I’m as rested and relaxed as I’ll be all week) for two and a half years now, and I’ve chronologically made my way through Slow Learner, V., Lot 49, Gravity’s Rainbow, Vineland, and currently, the first third of Mason & Dixon. Despite loads of warnings from folks who’ve read Pynchon, I’m liking Mason & Dixon the most of all! I think the heavy emphasis on dialogue (rather than all the monologues told from multiple perspectives, especially in GR and Vineland) is making it such an enjoyable read…like you said about some of the later books, it feels Dickensian to me. None I’ve disliked so far, though, and I still think V. was possibly the most enjoyable reading experiences of my life, and Gravity’s Rainbow one of the most mind-altering.

    Liked by 1 person

  4. I crashed on V sometime around 1970 and haven’t made it beyond the first few pages of any Pynchon since. Books that constantly invite readers to admire the cleverness of the writing give me the gripe. There is also the question of what one finds funny. Lots of the humor in Pynchon seems to depend on one’s knowledge of US pop culture. As an Australian, I find it hard to escape from same, and feel irritated rather than rewarded when I get a US pop culture allusion. Hence Pynchon’s jokes largely leave me stony faced. The main virtue I find in Pynchon is that Donald Trump could be one of his characters with no adaptation at all. For this alone one wishes him [Pynchon] all happiness on his 80th.


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