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, Wait, isn’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 Day, V. 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.