“The Crying of Lot 49” by Thomas Pynchon

Title: The Crying of Lot 49
Author: Thomas Pynchon
ISBN: 9780060931674
Pages: 160
Release date: 1966
Publisher: Harper Perennial
Genre: Postmodern fiction
Format: Paperback
Source: Personal collection
Rating: 3 out of 5


It’s bad enough when you find out your ex-boyfriend has died. It’s even worse when he has named you the executrix of his estate. But for Oedipa Maas, things really start to get complicated when she discovers and begins to unravel an ancient worldwide conspiracy.

Pierce Inverarity, a very wealthy real estate tycoon and Oedipa’s ex, has died, and Oedipa is named co-executor of his large—and tangled—estate. She leaves her moody husband, a used car salesman-turned-DJ, and her suburban home behind, and sets out for Pierce’s old headquarters in San Narciso (near Los Angeles).

Metzger, once a child actor and now a lawyer, is assigned to help Oedipa execute Pierce’s estate; he and Oedipa almost instantly begin having an affair.

In the midst of untangling Inverarity’s massive estate, Oedipa and Metzger see a play, The Courier’s Tragedy. Oedipa is fascinated by its depiction of a centuries-old conflict between two mail distribution companies, Thurn und Taxis and the Trystero (also spelled “Tristero”).

As Oedipa works through Inverarity’s estate, she begins discovering possible evidence for Trystero’s existence in Pierce’s documents and elsewhere. Along the way, Oedipa meets a host of unbelievably eccentric characters: a faux-Brit band; a therapist who once worked on captive Jews in Buchenwald; an engineer who claims to have defied entropy; and a handful of possible members of Trystero.


I first ran across this short novel in college, when a close friend was assigned to read it. I picked it up in her dorm room and read the first few chapters, and when I told her I was enjoying its eccentricities, she looked at me strangely (and a little painfully) and said that we must have very different literary tastes.

It wasn’t until I finally sat down to finish it that I understood what she meant. The novel slowly devolves from a humorous, slapdash account of a suburban housewife forced to face her past into a hallucinatory exploration of paranoia and conspiracy theories.

The absurdity of an underground mail system that uses a mysterious symbol and the acronym “W.A.S.T.E.” to communicate to its members is not lost on Oedipa. She begins to wonder if Inverarity invented the hoax just to live on, if not fondly in her memory than at least inevitably in her paranoia.

Trystero may be a conspiracy, a practical joke, a hallucination of Oedipa’s… but we’ll never know. Some have asserted that Pynchon’s exploration of conspiracy theories illustrates humans’ unreasonable quest for knowledge and certainty; his utterly uncertain ending certainly offers up proof of such an experiment.

Pynchon does an excellent job of blurring the lines between the characters’ realities, actions, and beliefs. He gradually introduces so much confusion to the tale that by the end, I wandered through the prose as Oedipa wanders the streets of San Francisco–terrified and desperately seeking answers.

By the end, I had NO idea what the book was about and was relieved to finally close it. Thank God it was short, or I’d really be pissed. Like Oedipa’s questions about the shadowy nature of Trystero, my questions about what actually happens in this book will never be answered.

Time included the novel in its TIME 100 Best English-language Novels from 1923 to 2005. I can’t help but wonder if literary critics have singled out his work to play a practical joke on readers—especially after having read a review of Gravity’s Rainbow over at the New Dork Review of Books.

Though this book is a fascinating take on 1960s sub- and counter-culture, I found its purposeful chaos and confusion too much to find it enjoyable. But that was probably Pynchon’s goal.

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