At the heart of Oedipa Maas's crazy predicament is her inability to tell the difference between her own mind and the world around her. Though she's aware that she (at least partially) creates her own reality, she is unable to tell how much of her world is real and how much is part of her fevered imagination. At the end of The Crying of Lot 49, she's left with a number of different versions of reality to choose from… but she doesn't know how to make the choice.
At the beginning of the novel, Oedipa Maas equates complexity with meaning and significance. But as the novel moves on, she is forced to look for meaning in simplicity.
Throughout the novel, Oedipa's real quest is to escape from her own mind into a world that she knows is real.
The Crying of Lot 49 doesn't exactly present the kind of vision of California that the Golden State would use in its tourism campaigns. Pynchon's view of California history (and, really, all of U.S. history) is super-paranoid.
The Tristero conspiracy is a conspiracy about the nature of America and the relationship between the counterculture and the mainstream. This book is both a parable about and a parody of America in the 1960s… but the times haven't changed as much as you might think.
In The Crying of Lot 49, we see that the existence of a counterculture is absolutely essential to the health of America because America is a country founded around a paranoid vision about centralized power.
Oedipa Maas's vision of America is superficial. At the end of the novel, she simply superimposes her own senses of claustrophobia, unhappiness, and paranoia onto the country as a whole.
Pynchon's The Crying of Lot 49 is basically held together by a big ol' metaphor; a figure of speech: the Tristero. But for Oedipa Maas, this "figure of speech" has to do with the nature of the world in which she lives. A lot of of her quest for the Tristero has to do with how—and to what extent—she can read meaning into a metaphor (the metaphor of the Tristero—it's super-confusing). And what's at stake is not only the truth, but Oedipa's sanity… and maybe the reader's sanity as well.
For both Oedipa and the reader, the Tristero functions more as a metaphor than as a real organization. Oedipa is unable to discover the truth about the Tristero because she approaches the metaphor as if it were real.
Oedipa begins to lose track of reality only when she reads too much meaning into other people's puns and figures of speech.
For a bookworm, Pynchon is surprisingly literate when it comes to modern science, and two scientific concepts—entropy and Maxwell's Demon—are totally central to understanding The Crying of Lot 49. The presence of a giant electronics and missile company also hovers over the plot, and throughout the novel we see the extent to which technology has come to affect every single aspect of modern life.
Technology is a dehumanizing force in The Crying of Lot 49, and what might be sincere human relationships take on a mechanical quality.
John Nefastis's ridiculous Perpetual Motion Machine reveals that metaphor has no place in science and highlights the enormous divide between literary and scientific modes of thought.
Don't read this book looking for hot and tempting sexytimes: sex in Pynchon's work is just another subject of parody. A bunch of characters have super-perverted desires… and the most nearly normal episode of knockin' boot involves putting on (not taking off) as many articles of clothing as possible. Sex seems to be everywhere in The Crying of Lot 49 (it was the swingin' 1960s, after all) and yet nowhere does it offer Oedipa a chance for happiness or emotional gratification.
Sex in Pynchon's novel is inherently perverted. The men view sex as a chance for dominance, whereas Oedipa views it as a chance for emotional connection.
The omnipresent obsession with young girls in Pynchon's novel emphasizes that there is no such thing as innocence in the world of Lot 49; innocents attract attention simply because they can still be corrupted.
Tons of characters in The Crying of Lot 49 use drugs, and a handful of 'em abuse drugs. Oedipa's therapist wants her to start dropping acid, and she ultimately loses her husband because he's on so much LSD that he's basically lost his mind. Plus, there's a bunch of drunkity-drunk-drunk scenes.
Drugs and alcohol are often shown to erode human relationships (as if Pynchon's characters needed help with that), and in some cases they seriously alter characters' relationships with reality (again—as if Pynchon's characters needed help in that department).
In Lot 49, Oedipa never chooses to use drugs or alcohol for their own sake. They are always forced upon her by someone with an agenda, and so drugs and alcohol are threatening.
In the novel, drugs and alcohol lead characters into isolation and madness.
There is very little love or human warmth in The Crying of Lot 49. From the very beginning, Oedipa Maas feels totally isolated and alone. She has a real sense that the void is just beneath her feet… and she doesn't even get by with a little (or any, really) help from her friends.
As complex as the novel becomes, at some level it can be read simply as Oedipa's attempt to escape from the feeling of being cold and alone—and her attempt to find a real human connection. No happy ending here, though.
The complexity of the Tristero conspiracy is born of the fact that Oedipa feels a need to construct an elaborate world around herself in order to escape from her feelings of despair and loneliness.
At the end of the novel, Oedipa's total isolation allows her to have a unique realization about the nature of America, and about how Tristero might unite the American dispossessed.
By the end of The Crying of Lot 49, Oedipa thinks that she may very well have lost her grip on reality. And with the company she keeps, who can blame her? To paraphrase the Cheshire Cat: they're all mad.
Nuttiness threatens a lot characters in the novel, and many totally fall over the edge into outright insanity. But the novel also suggests that some forms of madness are valid… and that Oedipa's over-the-top paranoia may be justified. After all, it's not paranoia if everyone actually is against you.
Since it's impossible to distinguish between Oedipa Maas's mind and reality, the only way to read Lot 49 is as a book about Oedipa's descent into insanity.
Oedipa Maas must cultivate paranoia in order to even imagine the scope and complexity of the Tristero conspiracy that is enveloping her life. She has to drive herself mad in order to grasp the world around her.