Thomas Pynchon was born in 1937 in Glen Cove, Long Island, New York, one of three children of Thomas Ruggles Pynchon, Sr. (1907-1995) and Katherine Frances Bennett (1909-1996). His earliest American ancestor, William Pynchon, emigrated to the Massachusetts Bay Colony with the Winthrop Fleet in 1630, then became the founder of Springfield, Massachusetts in 1636, and thereafter a long line of Pynchon descendants found wealth and repute on American soil. Aspects of Pynchon's ancestry and family background have partially inspired his fiction writing, particularly in the Slothrop family histories related in the short story "The Secret Integration" (1964) and Gravity's Rainbow (1973).

In an April 1964 letter to his agent, Candida Donadio, Pynchon wrote that he was facing a creative crisis, with four novels in progress, announcing: "If they come out on paper anything like they are inside my head then it will be the literary event of the millennium." In the mid-1960s, Pynchon lived at 217 33rd St. in Manhattan Beach, California, in a small downstairs apartment. In December 1965, Pynchon politely turned down an invitation from Stanley Edgar Hyman to teach literature at Bennington College, writing that he had resolved, two or three years earlier, to write three novels at once. Pynchon described the decision as "a moment of temporary insanity", but noted that he was "too stubborn to let any of them go, let alone all of them." Pynchon's second novel, The Crying of Lot 49, was published a few months later in 1966. Whether it was one of the three or four novels Pynchon had in progress is not known, but in a 1965 letter to Donadio, Pynchon had written that he was in the middle of writing a "potboiler". When the book grew to 155 pages, he called it, "a short story, but with gland trouble", and hoped that Donadio could "unload it on some poor sucker." The Crying of Lot 49 won the Richard and Hilda Rosenthal Foundation Award shortly after publication. Although 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 called 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 events 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, with both books dwelling on the detritus of American society and culture. The Crying of Lot 49 also continues Pynchon's strategy of composing parodic song lyrics and punning names, and referencing aspects of popular culture within his prose narratives. In particular, it incorporates a very direct allusion to the protagonist of Nabokov's Lolita within the lyric of a love lament sung by a member of "The Paranoids", an American teenage band who deliberately sing their songs with British accents (p. 17).

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