Three Books (that are good starting points for reading Thomas Pynchon)

Today is Pynchon in Public Day, so today’s Three Books blog offers 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 by Thomas Pynchon. First edition Penguin hardback, 2006. Jacket design my Michael Ian Kaye.

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. by Thomas Pynchon. Vintage UK trade paperback edition (1995). Cover by Paul Burgess.

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 by Thomas Pynchon. First edition hardback, Penguin, 2009. Jacket design by Tal Goretsky and Darren Haggar; image credited to Darshan Zenith and Cruiser Art.

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.

8 thoughts on “Three Books (that are good starting points for reading Thomas Pynchon)”

  1. I’m surprised that you don’t think IV’s plot threads “connect”, especially compared to GR. For me it’s the one Pynchon book where everything gets wrapped up neatly and there are answers to every question. I agree that it’s a great introductory point to Pynchon, though.

    Liked by 1 person

  2. Vineland is the best intro. Sure, the Pynchonian Prattling Pawns (self-selected elite readers of his work) hate that one, but it’s got readability, funny characters, funny character names, plots turning back on themselves, and other standard Pynchonian vehicles in smaller, easier-to-digest doses.

    The other novels are too Pynchon-y for anyone not already converted to the PPP group membership.

    Lot 49 may be short but it’s not clear or easy. In my non-PPP view it seems more like a Steve Erickson novel than a Thomas Pynchon one.

    Perhaps the unfamiliar could do without the “I’m smarter than you, you’re missing the inside jokes” observations.


  3. I second the recommendation of Vineland as a way to dip your toe in, although I didn’t find Crying particularly difficult. There’s always the volume of stories, Slow Learner. Mason & Dixon was the last Pynchon I read for the first time. I don’t regret reading it but it was a hell of a slog. I wouldn’t devote a month to it again. I would like to revisit V and Gravity’s Rainbow someday.


  4. I have tried multiple times to get through The Crying of Lot 49 and just couldn’t do it. V is so far the only book of his I’ve been able to finish, but after seeing Inherent Vice in the theater, I want to give his other books a go. Thanks for the insight & suggestions! Against the Day is already on my shelf so I suppose that’s next.


  5. I loved Lot 49 and it was the ideal intro to him for me, but I also had a lot of challenging writers on my belt before I finally reach Pynchon. I’d agree with you and say Inherent Vice would be the ideal intro because it goes on his weird tangents but also has a pretty solid and (compared to his other work) traditionally coherent plot.

    I only recently finally read one of his bricks, his debut V. which at once exhausted and amazed me (I wrote rambling review of it

    Reading Gravity’s Rainbow next, and you’ve made me even more excited for it.


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