The Crying of Lot 49 Study Guide

Thomas Pynchon is famously unforthcoming about his private life: in more than a half-century, he has never granted an interview, talked openly about his past, or allowed his photo to be published. However, this has not prevented critics and journalists from assembling a sketch of his life trajectory. Pynchon was born on Long Island to a comfortable middle-class family with aristocratic roots stretching back to 1630s Massachusetts. After a reportedly traumatic upbringing full of family conflict, Pynchon finished high school at 16 and briefly studied engineering physics at Cornell University before leaving for a short stint in the U.S. Navy. Upon returning to Cornell, he switched his major to English, started writing short stories based on his time in the navy, and even tried his hand at writing opera libretti. In the early 1960s, he spent some time sleeping on friends’ couches in New York, until he landed a job as a technical writer for a missile technology project with Boeing in Seattle. As soon as he published his first novel, V. (1963), Pynchon quit Boeing and moved to Mexico City, then to Los Angeles, where he stayed until the early 1970s. Pynchon’s landmark 1973 novel Gravity’s Rainbow, which was heavily influenced by his time at Boeing, won him widespread recognition, in addition to a 1974 National Book Award. (Pynchon refused to attend the ceremony and sent comedian Irwin Corey on his behalf.) Pynchon published virtually nothing for the next decade. During this period, he frequently lived on the road, and his identity and location became the subject of widespread speculation in the media—one journalist even tried to hunt him down in an isolated shack in the Northern California woods. Soon after winning a MacArthur “Genius Grant” in 1988, however, Pynchon married his literary agent Melanie Jackson and moved to the Upper West Side of New York City, where he reportedly continues to live and socializes widely with friends and other writers.

The Crying of Lot 49 is steeped in the contradictions and countercultures of 1960s America. For instance, Pynchon parodies American Beatlemania through a rock band called The Paranoids, who dress like their idols, write Beatles cover songs, and sing in English accents (even though they are American). The Cold War and the Vietnam War constantly lurk in the background of the novel, especially in its references to the giant military contractor Yoyodyne, which is busy developing missile technology as part of the nuclear arms race against the Soviet Union. Marijuana and LSD, which became the subject of national debate in the 1960s, also make prominent appearances in the novel. However, The Crying of Lot 49 also centers on a purported historical conspiracy that involves the private courier service run by the Princely House of Thurn and Taxis, which started as early as the 1200s and was totally dominant for several hundred years in parts of Europe. The Thurn and Taxis stamps and iconography that Pynchon references are likely historically authentic. Similarly, the conspiracy theorist and postal underground leader Mike Fallopian is writing a study of 19th-century private postal services in the United States, a period during which the federal government began buying and outcompeting private postal companies in order to establish a unified national service.

While The Crying of Lot 49 is Thomas Pynchon’s shortest, most accessible, and most widely-read work, he is far more famous for two longer and more elaborate novels that take up similar thematic material. One is his debut work V. (1963), which follows a navy veteran who uncovers a complicated plot surrounding the letter “V.” The other is his masterpiece Gravity’s Rainbow (1973), set in the end and aftermath of World War II, which centers on the search for secret German missile technology. Pynchon’s other novels include Vineland (1990), which juxtaposes a hippie commune in the 1960s California of The Crying of Lot 49 with the backlash to American counterculture in the 1980s. Some novels that influenced Pynchon’s early work include Jack Kerouac’s On the Road (1957), which many commentators have argued influenced Oedipa Maas’s wanderlust and search for meaning in post-World War II California in The Crying of Lot 49. William Gaddis’s The Recognitions (1955) also takes up similar questions of reality and authenticity through the lens of art. Throughout The Crying of Lot 49, Pynchon continually parodies Vladimir Nabokov’s infamous Lolita (1955) by having his male characters proclaim their sexual interest for underage girls. And the character of Dr. Hilarius is clearly based on the controversial psychologist Timothy Leary, who famously advocated for the use of psychedelic drugs in works like The Psychedelic Experience (1964). A few of the most prominent postmodern American novels influenced by Pynchon’s work include David Foster Wallace’s famously encyclopedic Infinite Jest (1996), which is often compared to Gravity’s Rainbow, and Don DeLillo’s White Noise (1985), an influential satire of academia and consumerism.