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why Pynchon has not won ? one perspective:

“With the important caveat that negative or mixed literary reviews can often be more entertaining and instructive than wholly positive ones, it seems William Deresiewicz’s assessment of Tom McCarthy’s novelistic output could be boiled down to two words: bad Pynchon... One suspects the real reason Thomas Pynchon has never been awarded the Nobel Prize in Literature is not that he hasn’t proved hugely influential on subsequent generations of writers, but rather that he has—and with largely unfortunate results.

Unlike the still-growing crop of (almost exclusively male) postmodern creators of boring, inelegant, ponderous, theory-driven doorstop novels, Pynchon’s first books, V. and The Crying of Lot 49, carry their poststructuralism lightly and crackle with wit, satire, and well-crafted riffs on cultural-historical moments past. Since then, a whole subindustry of academic creative writing grinds ever forward, devoted to failed attempts at rewriting Pynchon’s 1973 masterpiece, Gravity’s Rainbow”

per http://www.thenation.com/article/letters-514/
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Nobel Prize 2015 · General discussion