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The most accessible of Pynchon's novels, the book is about a fictional conflict between the two first mail distribution companies to exist, Thurn und Taxis (which actually existed and was the first firm to distribute postal mail) and Tristero, which is a fictional invention of Pynchon's.
After being defeated by Thurn und Taxis in the 1700s, the Tristero organization goes underground and continues to exist, with its mailboxes in the least suspected places, often appearing under their slogan W.A.S.T.E., an acronym for We Await Silent Tristero's Empire, and also a smart way of hiding their post-boxes disguised as regular waste-bins. In the plot of the novel, the existence and plans of the shadowy organization are revealed bit by bit...
... or, then again, it is possible that the Tristero does not exist at all. The novel's main character, Oedipa Maas, is buffeted back and forth between believing and not believing in them, without ever finding firm proof either way. The Tristero may be a conspiracy, it may be a practical joke, or it may simply be that Oedipa is hallucinating all the arcane references to the underground network, that she seems to be discovering on bus windows, toilet walls, et cetera.
All of this forms the background for a story set in present-day California.
Almost a fifth of the book -- the central portion -- is devoted to a detailed description of a performance of an imaginary Jacobean revenge play involving intrigues between Thurn und Taxis and Tristero.
As in his earlier novel, V., Pynchon seems to be making a point about human beings' need for certainty, and their need to invent conspiracy theories to fill the vacuum in places where there is no certainty.
Also, as in the earlier novel, the book is laced with original song lyrics, outrageously named characters (e.g. Genghis Cohen, Manny DiPresso), and numerous references both to pop culture and high culture.
In addition to the above-mentioned postmodernist interpretation, there is also the theory that Pynchon was influenced by the racial tensions in southern California that would later turn into riots across the country.
As ever with Pynchon's writing, the labyrinthine plots offer a myriad of interconnecting cultural refernces. While a basic knowledge of some of these may help decipher the plot, ultimately the enjoyment of the literary games is all that is needed to understand the novel. J. Kerry Grant wrote A Companion to the Crying of Lot 49 (BooksEnthsiast.com) in attempts to catalogue these references, but it is neither definitive nor complete, and could not possibly be.