The Crying of Lot 49 by Thomas Pynchon is his shortest and most accessible work. The book follow our heroine, Oedipa Mass, as she unravels the estate of her late ex-boyfriend Pierce Inverarity.  When she digs into his estate she comes across a centuries old conspiracy. As Oedipa journeys across the California landscape as she moves deeper into the conspiracy and starts realizing that she truly can’t tell if this is a conspiracy or a giant hoax being played on her.

Our heroine Oedipa Maas starts the story off by finding out that her real-estate mogul ex-boyfriend died and made her executor of his estate. If that isn’t enough her husband, a disc jockey at KCUF, is shell shocked from his time at a used car dealership. Oedipa talks it over with her therapist (Dr. Hilarious) who uses his techniques (attempting to cure patients by making faces) to help her and recommends some medicine (LSD) to help her. Then Oedipa leaves on her journey.

It’s the stamps that start everything. Oedipa notices a typo on a cancellation (potsmaster), a muted horn symbol and a reference to WASTE. Her investigations lead her to a ancient play that was censored and a name Tristero. Everything seems to point to a underground postal system that competes with the USPS and has been around for centuries.

Oedipa continues following all the clues and starts getting deeper and deeper into WASTE and Tristero. But she soon realizes that every clue she finds can be traced back to Inverarity. And she has to decide if their is a giant centuries old worldwide conspiracy or a hoax being played on her by a dead ex-boyfriend. And it all comes back to the stamps and the book ends as Oedipa waits to find out the truth (as we find the meaning of the title).


The Crying of Lot 49 is Pynchon’s short and most accessible novel. It’s a great romp across California in the mid-60s with a load of paranoia and conspiracy theories abound. Pynchon has to some extent disowned the book (as mentioned in the introduction to Slow Learner) and it’s hardly a novel (clocking in at a mere 138 pages), but it is an enjoyable and mind-bending novel that must be read.