The Crying of Lot 49, 1965
by Thomas Pynchon
Trade Paperback, 152 pages
Written before V. but published after that novel's success, The Crying of Lot 49 has more in common with the short fiction in Pynchon's Slow Learner than any of his other novels. It is less than half the length of Vineland, Pynchon's second-shortest novel, and unlike any of the other books (mostly) follows a single protagonist down a (reasonably) straightforward plot. Pynchon himself is said to consider this a "journeyman effort," better than the "apprentice" works of his early short fiction but not up to the standard of his later novels.
He's probably too hard on himself. While Lot 49 is comparatively simple for those who have absorbed Pynchon's longer works, it's an excellent introduction to his writing, and stands as a great work in its own right. As the book opens, a young Southern California woman named Oedipa Maas is named the executor of the will of Pierce Inverarity, a former lover of hers. What starts out as a largely formal request ends up leading Oedipa into a twisty maze of maybe-conspiracies involving a shadowy postal service war from centuries past, a possible crime against humanity in the production of cigarette filters, a device that will violate the Second Law of Thermodynamics... in other words, into a crazy world full of the kinds of strangeness that is Pynchon's forte.
In this way, The Crying of Lot 49 provides a sort of introduction to Pynchon's work for those who are not already familiar with it, and a sort of filtering device for those who are. Oedipa Maas falls through the metaphorical rabbit hole into this strange world where no one seems innocent, a world filled with the cast-outs and burn-outs of society, a world denied by the Authorities, whether they be in government, industry, academia, what have you. Or does she? -- there is some indication that Pierce might have set up the whole thing to simply play a trick on poor insulated and isolated Oedipa. It is the spectre of doubt, the sense that at any time the rug could be pulled from under your feet even after the wool has been pulled off of your eyes that makes Lot 49 (and by extension Pynchon's whole oevure) so compelling.
Perhaps we the reader are supposed to treat Pynchon's corpus the way Oedipa treats the sights she sees in the underworld in Crying of Lot 49. Perhaps Oedipa is in that sense a reader stand-in -- if so, the ending of the novel suggests that true understanding is forever out of our reach, that Someone or Something will forever keep us from the Truth. Perhaps. Pinning down exactly what Pynchon wants the reader to take away from any given passage is notoriously difficult, not least because passages often seem to contradict each other, and Meaning is elusive. Just as in life.
The Crying of Lot 49 is also memorable for its sense of fun and games, even if some of the humor is as pitch-black as it gets. In one memorable sequence (which was echoed later on in Vonnegut's Slaughterhouse V, whether knowingly or not I can't say) Oedipa watches a movie on TV with a lawyer Paul Metzger which has (maybe) been aired out of sequence. During this scene Metzger is also seducing Oedipa and providing exposition to the reader, in what is one of the most convoluted and strange sequences I've read in any novel. That Pynchon pulls this off with humor, clarity, and Meaning is astonishing and gives indications of what we could expect from him later on.
My recommendation here: read it twice. The original hardcover (and the paperback I own) is 152 pages, and is perfectly able to be read in a single extended sitting. Reading it again soon thereafter helps to make some of the themes of the novel more clear, and to make sense of Pynchon's often obscure prose style. It's a strange read, but definitely worth the time for anyone looking to see what Pynchon is all about -- try Gravity's Rainbow later once you get to the point of this shorter work.