The Crying of Lot 49 was written in the 1960s, one of the most politically and socially turbulent decades in U.S. history. The decade saw the rise of the drug culture, the Vietnam War, the rock revolution, as well as the birth of numerous social welfare programs after the Democrats swept Congress in the 1964 elections. This was also the decade of John F. Kennedy's assassination, Martin Luther King's assassination, Civil Rights, and, to some extent, women's rights. The novel taps into this explosion of cultural occurrences, depicting a dramatically fragmented society. The Crying of Lot 49 contains a pervasive sense of cultural chaos; indeed, the book draws on all areas of culture and society, including many of those mentioned above. In the end, the novel's protagonist, Oedipa Maas, finds herself alone and alienated from that society, having lost touch with the life she used to lead before she began her attempt to uncover the mystery of the Tristero. The drug culture plays a big part in this sense of isolation. The world around Oedipa seems to be a world perpetually on drugs, manic and full of conspiracies and illusions. And though that world is exciting and new, it is also dangerous: drugs contribute to the destruction of Oedipa's marriage, and drugs cause Hilarius to go insane. Oedipa hallucinates so often that she seems to be constantly high, and ultimately, this brings her nothing but a sense of chaotic alienation.
Many of the problems with chaos found in the novel are tied in to the idea of communication. The major symbol of order in the novel, Maxwell's Demon, cannot be operated because it requires a certain unattainable level of communication. Letters in the novel, which should be clear and direct forms of stable communication, are ultimately meaningless. The novel also contains a mail-delivery group that requires its members to mail a letter once a week even if they have nothing to say. Indeed, the letter Oedipa receives in chapter one may itself be meaningless, since it is the first step in what may be nothing more than a big joke played on Oedipa. The religious moment Oedipa experiences in chapter two seems for a moment to promise the possibility of some kind of communication being communicated, but the process breaks down. Religion, language, science, all of the purveyors of communication, and through that communication a sense of wholeness, do not correctly function in the novel.
Related to the theme of the problem of communication is the novel's representation of the way in which people impose interpretation on the meaningless. It is very telling that Oedipa wants to turn the mystery of the Tristero into a "constellation," which is not really an example of true order. Solar systems are simply mankind's way of imposing an artificial but pleasing order on the randomness of outer space. It is, furthermore, an imposition of a two-dimensional structure onto a three-dimensional reality. Oedipa's quest to construct a constellation seems to indicate that she is only looking for a superficial system. Indeed, she never succeeds in figuring out the meaning behind the Tristero, and, further, the novel ends with the very strong likelihood that the mystery may hold no mystery at all. And just as she is unable to piece together the puzzle of the Tristero, she is similarly unable to refashion her life after it begins to fall apart. Even the United States government, which tries to impose an order on the world of mail delivery, cannot prevent side groups from springing up to undermine its work.
There are two concepts underlying all this: puns and science. The novel is full of puns and language games of all sorts. For instance, the odd names of the novel's characters are a type of play on different words and their symbolic baggage. Another example is the concept of the word "lot" in the title, which actually occurs several times in the book but does not relate to anything in the story until the last few pages. Also, we see that Mucho's radio station spells "fuck" when read in reverse, forming another little language game that does not have necessarily any inherent meaning but does indicate an interest in manipulating language for intellectual enjoyment. Language is the means through which the story is communicated, and Pynchon has chosen to use a language full of jokes, puns, and satires. Science seems to stand in opposition to the chaos of language that all of Pynchon's manipulation suggests. Science is ordered and coherent and offers a body of definite knowledge that all can study. And yet, even the coherence of science is undermined in the existence of Maxwell's Demon and the figure of Dr. Hilarius. Though pure science may offer coherence, the uses to which that science is put, the interpretations imposed on that science, can scatter that coherence to the wind.
More than anything else, The Crying of Lot 49 appears to be about cultural chaos and communication as seen through the eyes of a young woman who finds herself in a hallucinogenic world disintegrating around her.