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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 in literature|1958]] novel ''[[Warlock (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 (although Nabokov's wife, Vera, who graded her husband's class papers, commented that she remembered his distinctive handwriting; his later handwriting appears unexceptional), other teachers at Cornell, like the novelist James McConkey, recall him as being a gifted and exceptional student. Pynchon received his BA in June 1959.

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, Washington|Seattle]], where he compiled safety articles for the ''Bomarc Service News,''<ref>Wisnicki 2000-1</ref> 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.

From the mid-1960s Pynchon has also regularly provided blurbs and introductions for a wide range of novels and non-fiction works. One of the first of these pieces was a brief review of Hall's ''Warlock'' which appeared, along with comments by seven other writers on "neglected books", as part of a feature entitled "A Gift of Books" in the December 1965 issue of ''Holiday.''

In April 1964, Pynchon wrote to his agent, Candida Donadio, that he was facing a creative crisis, with four novels in progress, and that "If they come out on paper anything like they are inside my head then it will be the literary event of the millennium."<ref>Gussow 1998</ref> In December 1965, Pynchon politely turned down an offer to teach literature at Bennington College, writing that he had resolved, two or three years earlier, to write three novels at once.<ref>McLemee 2006</ref> Pynchon called the decision “a moment of temporary insanity,” but noted that he was “too stubborn to let any of them go, let alone all of them.” P

A collection of Pynchon's early short stories, entitled ''[[Slow Learner]]'', was published in 1984, with a lengthy autobiography|autobiographical introduction. In October of the same year, an article entitled "Is It O.K. to Be a Luddite?" was published in the ''New York Times Book Review''. In April 1988, Pynchon contributed an extensive review of Gabriel García Marquéz's novel, ''Love in the Time of Cholera'', to the ''New York Times'', under the title "The Heart's Eternal Vow". Another article, entitled "Nearer, My Couch, to Thee", was published in June 1993 in the ''New York Times Book Review'', as one in a series of articles in which various writers reflected on each of the Seven Deadly Sins. Pynchon's subject was "Sloth".

Pynchon's fourth novel, ''[[Vineland]]'', was published in 1990. The novel is set in California in the 1980s and 1960s, and describes the relationship between an [[Federal Bureau of Investigation|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.<ref>See, for example, Grimes 1993, CNN Book News 1999, Ervin 2000</ref> 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.

Pynchon's fifth novel, ''[[Mason & Dixon]]'', was published in 1997. Pynchon began writing it as early as January 1975.<ref>Gussow</ref> The meticulously-researched novel is a sprawling saga recounting the lives and careers of the English astronomer, [[Charles Mason]], and his partner, the surveyor [[Jeremiah Dixon]], and the birth of the [[American Revolution|American Republic]]. While it received some negative reviews, the great majority of commentators acknowledged it as a welcome return to form, and some, including Bloom, have called it Pynchon's greatest work to date.