The Crying of Lot 49 (1966) is a short novel by Thomas Pynchon that handles topics related to the US counterculture movement and the 1960s at large. In the novel, Oedipa Maas unearths a centuries-old conspiracy about warring mail-delivery firms. This discovery leads her along an absurdist investigation of the firms and their motivations. The novel has been heralded as one of the best English-language novels of the 20th century and is considered a primary example of postmodernist literature. Its unconventional narrative style, irreverent treatment of characterization, and scrutiny of the limits of knowledge all contribute to its classification as a postmodernist novel. It is also considered a work of satire. Critics often point to it as one of Pynchon’s three masterpieces, the others being V. and Gravity’s Rainbow.

This guide uses the 2022 Vintage Classics edition.

Content Warning: This novel discusses individuals who have an addiction and a substance-use disorder. The novel handles topics of substance use and addiction. It also handles topics of suicide, self-harm, and mental illness.

Plot Summary

Oedipa Maas lives in Kinneret, California, with her husband, Mucho Maas. After attending a party, she returns home to find a letter. The letter informs her that Pierce Inverarity, her ex-boyfriend, is dead and she has been appointed the executor of his estate. Though she knows nothing of what this entails, Oedipa accepts the role and travels to Pierce's hometown, San Narciso. She meets a handsome lawyer named Metzger. While they work to untangle the complicated estate in a hotel room, they begin an affair. During their research into the Inverarity Estate, Oedipa discovers Pierce possessed a large collection of stamps. She visits a bar named the Scope with Metzger, where she meets a right-wing conspiracist named Mike Fallopian. Mike is a member of the Peter Pinguid Society, and he details his complaints regarding the United States Postal Service's monopoly on mail delivery. In the bathroom, Oedipa notices a strange symbol, ostensibly a muted post horn, drawn on the walls next to the name Kirby and the acronym W.A.S.T.E. Oedipa does not know what they mean.

Oedipa and Metzger track down Pierce's land holdings in Fangoso Lagoons. They encounter a lawyer named Manny di Presso, who was hired by a client to sue Pierce's estate. Manny claims his client sold human bones to Inverarity but was not paid. The bones were ground up to make charcoal for use in cigarette filters. Upon hearing the story, a member of the Paranoids—the rock band that has followed Oedipa since her stay in the San Narciso hotel—points out the similarity in this situation to a Jacobean revenge drama titled The Courier's Tragedy. Oedipa and Metzger buy tickets for a local production of the play, during which Oedipa is struck by the inclusion of the word Tristero. When she speaks with the director, Randolph Driblette, he tells her she is overanalyzing minor details. Oedipa plans to call Driblette later.

After consulting Pierce's will, Oedipa attends a meeting of Yoyodyne shareholders, a company in which Pierce’s estate holds stock. Slipping away from a subsequent factory tour, she finds Stanley Koteks in his office. He is drawing the same symbol of the muted horn she saw in the bathroom at the Scope. Stanley talks about John Nefastis, a scientist who invented a perpetual-motion machine. He tells Oedipa to visit Nefastis. In the meantime, Oedipa buys an anthology of Jacobean plays. The version of The Courier's Tragedy in the anthology is different from Driblette's production, however, as it does not mention Tristero. Hoping to meet the book's publisher, she stops first at a senior-care facility (also owned by Pierce) and talks to a man whose ring features the same muted-post-horn symbol. She also consults a stamp expert named Genghis Cohen to analyze Pierce's collection. Cohen notices some stamps also feature the muted post horn. He suggests the symbol is a muted variant of the coat of arms of Thurn and Taxis, an 18th-century postal monopoly that crushed all opposition, including Tristero (or Trystero in this case), a competing postal company. Oedipa is confused by the mystery but wonders if Tristero is some kind of underground counterculture society.

Oedipa finds Nefastis in Berkeley. He tells her she lacks the mental talents to use his machine; she runs out of his house after he propositions her for sex. For the rest of the night, Oedipa wanders the city in a hallucinatory daze. She sees the muted-post-horn symbol everywhere, and, as dawn arrives, an elderly man asks her to deliver a letter to a group of people beneath a freeway. On the way to the freeway, she sees a garbage can with W.A.S.T.E. written on it, and a youngster places a letter inside of it. A mail courier picks up the letter, and Oedipa follows him on his delivery route, deciding to stop following the mail route after it ends up at John Nefastis’s house.

Overwhelmed, Oedipa returns home and then visits her therapist, who now suffers from psychosis. He locks himself in his office with a rifle and, as Oedipa tries to help him, confesses he worked in a Nazi concentration camp. The news media covers the event, and, as the police take Dr. Hilarius away, Oedipa sees her husband outside. As she talks to Mucho, she realizes he now has an addiction to LSD and also suffers from psychosis. She leaves, feeling even more alone.

Oedipa talks to an English professor named Emory Bortz. She asks him about revenge plays such as The Courier's Tragedy. Bortz tells her about the Tristero, whose history dates back to Europe in the 1500s. Though she would like to ask Driblette why he produced a specific version of the play that was used, she learns, as religious propaganda, she discovers he has recently died by suicide. Feeling despondent, alone, and on the verge of giving up, Oedipa returns to Mike Fallopian. He suggests the entire mystery may be an elaborate joke, played on her by Pierce. Oedipa rejects this but cannot deny that everything leads back to Pierce's estate. Genghis Cohen contacts her, explaining that Pierce's stamp collection is set to be auctioned. A mysterious buyer may be at the auction, so Oedipa hopes he may have the answers she needs. Genghis explains the rules of the auction as Oedipa sits down and waits for the crying of Lot 49.