Childhood and education Pynchon attended Oyster Bay High School, where he wrote for the school newspaper and excelled in his studies. After graduating in 1953, he studied engineering physics at Cornell University, but left at the end of his second year to serve in the U.S. Navy. In 1957 Pynchon returned to Cornell to pursue a degree in English. His first published story, "The Small Rain", appeared in the Cornell Writer in May 1959, and narrates an actual experience of a friend who had served in the army; subsequently, however, episodes and characters throughout Pynchon's fiction draw freely upon his own experiences in the navy.

While at Cornell, Pynchon became a friend of Richard Fariña, and both briefly led what Pynchon has called a "micro-cult" around Oakley Hall's 1958 novel Warlock. (He later reminisced about his college days in the introduction he wrote in 1983 for Fariña's novel Been Down So Long It Looks Like Up to Me, first published in 1966.) Pynchon also reportedly attended lectures given by Vladimir Nabokov, who then taught literature at Cornell. While Nabokov later said that he had no memory of Pynchon (though Nabokov's wife, Vera, who graded her husband's class papers, commented that she remembered his distinctive handwriting), other of Pynchon's lecturers at Cornell recall him as being a gifted and exceptional student. Pynchon received his BA in June 1959.

Early career After leaving Cornell, Pynchon began to work on his first novel. From February 1960 to September 1962 he was employed as a technical writer at Boeing in Seattle, where he compiled safety articles for the Bomarc Service News (see Wisnicki 2000-1), a support newsletter for the BOMARC surface-to-air missile deployed by the U.S. Air Force. Pynchon's experiences at Boeing inspired his depictions of the "Yoyodyne" corporation in V. and The Crying of Lot 49, and both his background in physics and the technical journalism he undertook at Boeing provided much raw material for Gravity's Rainbow. When it was published in 1963, Pynchon's novel V. won a William Faulkner Foundation Award for best first novel of the year.

After resigning from Boeing, Pynchon spent time in New York and Mexico before moving to California, where he was reportedly based for much of the 1960s and early 1970s, most notably in an apartment in Manhattan Beach (see Frost 2003). In 1964 his application to study mathematics as a graduate student at the University of California, Berkeley, was turned down (Royster 2005). In 1966 he wrote a first-hand report on the aftermath and legacy of the Watts riots in Los Angeles. Entitled "A Journey Into the Mind of Watts", the article was published in the New York Times Magazine (Pynchon 1966).

Pynchon's second novel, The Crying of Lot 49, is also set in California. It was published in 1966, and won the Richard and Hilda Rosenthal Foundation Award. Although it is more concise and linear in its structure than Pynchon's other novels, its labyrinthine plot features an ancient, underground mail service known as "The Tristero" or "Trystero", a parody of a Jacobean revenge drama entitled The Courier's Tragedy, and a corporate conspiracy involving the bones of World War II American GIs being used as charcoal cigarette filters. It proposes a series of seemingly incredible interconnections between these and other similarly bizarre revelations that confront the novel's protagonist, Oedipa Maas. Like V., the novel contains a wealth of references to science and technology and to obscure historical events, and both books dwell upon the detritus of American society and culture. The Crying of Lot 49 also continues Pynchon's habit of composing parodic song lyrics and punning names, and referencing aspects of popular culture within his prose narrative. In particular, it incorporates several allusions to Nabokov's Lolita.

In 1968 Pynchon was one of 447 signatories to the "Writers and Editors War Tax Protest". Full page advertisements in the The New York Post and The New York Review of Books listed the names of those who had pledged not to pay "the proposed 10ncome tax surcharge or any war-designated tax increase", and stated their belief "that American involvement in Vietnam is morally wrong" (New York Review of Books 1968:9).

Gravity's Rainbow and Pynchon's rise to prominence Pynchon's most celebrated novel is his third, Gravity's Rainbow, published in 1973. An incredibly intricate and allusive fiction which combines and elaborates on many of the themes of his earlier work, including preterition, paranoia, racism, colonialism, conspiracy, synchronicity, and entropy, the novel has spawned a wealth of commentary and critical material, including two reader's guides (Fowler 1980; Weisenburger 1988), books and scholarly articles, on-line concordances and discussions, and art works, and is regarded as one of the archetypal texts of American literary postmodernism. The major portion of Gravity's Rainbow takes place in London and Europe in the final months of the Second World War and the weeks immediately following VE Day, and is narrated for the most part from within the historical moment in which it is set. In this way, Pynchon's text enacts a type of dramatic irony whereby neither the characters nor the various narrative voices are aware of specific historical circumstances, such as the Holocaust, which are, however, very much to the forefront of the reader's understanding of this time in history. Such an approach generates dynamic tension and moments of acute self-consciousness, as both reader and author seem drawn ever deeper into the "plot", in various senses of that term. Encyclopedic in scope, the novel also displays enormous erudition in its treatment of an array of material drawn from the fields of psychology, chemistry, mathematics, history, religion, music, literature and film. Perhaps appropriately for a book so suffused with engineering knowledge, Pynchon reputedly wrote the first draft of Gravity's Rainbow in longhand on engineer's graph paper, in California and Mexico City.

Gravity's Rainbow was a joint winner of the 1974 National Book Award for Fiction, along with Isaac Bashevis Singer's A Crown of Feathers and Other Stories. In the same year, the fiction jury unanimously recommended Gravity's Rainbow for the Pulitzer Prize; however, the Pulitzer board vetoed the jury's recommendation, describing the novel as "unreadable", "turgid", "overwritten", and in parts "obscene", and no prize was awarded (Kihss 1974). In 1975, Pynchon declined the William Dean Howells Medal of the American Academy of Arts and Letters.

Post-Gravity's Rainbow A collection of Pynchon's early short stories, entitled Slow Learner, was published in 1984, with a lengthy autobiographical introduction. Pynchon's fourth novel, Vineland, was published in 1990, and was regarded as a disappointment by the majority of reviewers and critics. The novel is set in California in the 1980s and 1960s, and describes the relationship between an FBI COINTELPRO agent and a female radical filmmaker. Its strong socio-political undercurrents detail the constant battle between authoritarianism and communalism, and the nexus between resistance and complicity, but with a typically Pynchonian sense of humor.

In 1988, he received a MacArthur Fellowship and, since the early 1990s at least, many observers have mentioned Pynchon as a Nobel Prize contender (see, for example, Grimes 1993; CNN Book News 1999; Ervin 2000). Renowned American literary critic Harold Bloom has named him as one of the four major American novelists of his time, along with Don DeLillo, Philip Roth, and Cormac McCarthy.