From V to Vineland and Inherent Vice: Thomas Pynchon's books – ranked!

The Guardian

a day ago

A collection of early short stories that is chiefly of interest for the introduction, in which the author spells out why he thinks they fail. Pynchon does not spare himself but, unfortunately, he is right. For aficionados only.
Typical line 'Downstairs, Meatball Mulligan's lease-breaking party was moving into its 40th hour.'Pynchon tropes Wacky names, pastiche songs
Practically plotless, prolix and gargantuan, this novel landed with a thump following a nine-year gap. Characters fragment and double in a bewildering array, the style pastiches pulp novels, adventure stories and science fiction. It does not add up to more than the sum of its admittedly ingenious parts.
Typical line 'Taking quick looks behind him on the trail, Lew Basnight was apt to see things that weren't necessarily there.'Pynchon tropes Real-life events, pastiche songs
Pynchon's most recent novel is a lightweight. The protagonist, Maxine Tarnow, mother of two, longsuffering partner to a feckless financier, finds herself chasing shadows around Manhattan's Silicon Alley. Maxine's skills as a fraud investigator are put to the test unravelling the machinations of the nasty controller of a computer security firm who will do anything to get his hands on a virtual reality simulator called DeepArcher (geddit?). There are plentiful puns, red herrings and surnames that serve as possibly unhelpful acronyms – the usual Pynchon ingredients, in other words. Here they fail to cohere into an entirely satisfying whole.
Typical line 'Paranoia's the garlic in life's kitchen … you can never have too much.'Pynchon tropes Pastiche songs, sex, historical events
It is 1984, the year of Reagan's re-election but for Zoyd Wheeler, Los Angeles-based veteran of the radical left, time has stopped. His wife, Frenesi, has left him to raise their daughter, Prairie, alone and he resorts to dismal acts of self-sabotage in order to qualify for government benefits. Prairie, in turn, flees the family coop to track down her mother, a subversive turned informant in league with federal baddy Brock Vond. Pynchon's themes are prescient – surveillance, media saturation, generational miscommunication – but his aim is off.
Typical line 'If patterns of ones and zeros were 'like' patterns of human lives and deaths, if everything about an individual could be represented in a computer record by a long string of ones and zeros, then what kind of creature would be represented by a long string of lives and deaths.'Pynchon tropes Sex, drugs, anagrams
Sincerity is not a quality readily associated with Pynchon, but his debut novel displays an affection for his characters that would later take second place to irony. The story bounces between Benny Profane, unemployed sailor, and Herbert Stencil, obsessive seeker of the elusive V. The language shows its age in places, but the plight of people determined to keep themselves in the dark is as relevant as ever.
Typical line 'Perhaps history this century … is rippled with gathers in its fabric such that if we are situated, as Stencil seemed to be, at the bottom of a fold, it's impossible to determine warp, woof or pattern anywhere else.'Pynchon tropes Pastiche songs, sex, real-life events
The author regretted publishing this novel but he was being unduly harsh on himself. Short, funny and shot through with allusions you can choose to follow or ignore, the story of Oedipa Maas's search for the meaning behind the supposed rivalry of postal companies is the literary equivalent of non-Euclidean geometry.
Typical line 'Oedipa wondered whether, at the end of this (if it were supposed to end), she too might not be left with only compiled memories of clues, announcements, intimations, but never the central truth itself.'Pynchon tropes Sex, pastiche songs
Wilfully weird, often sordid and occasionally borderline unintelligible, Pynchon's seventh novel was adapted for the big screen by Paul Thomas Anderson in 2014. The adaptation was nominated for an Oscar, making Pynchon as mainstream as he's ever likely to get. Larry 'Doc' Sportello is a private investigator with a broken heart and a huge appetite for marijuana. His ex-girlfriend reappears out of nowhere, implores Doc to find her married lover, then promptly vanishes again. At the heart of the murky tale lurks the sinister presence of the Golden Fang, a vessel that means, as Doc surmises, 'a lot of things to a lot of people' – all of them unsavoury.
Typical line ''What,' Doc wondered aloud, 'the fuck is going on here?''Pynchon tropes Drugs, sex, rock'n'roll
This kaleidoscopic tour de force cemented Pynchon's reputation as a writer of baffling, farcical and profound genius. A chief delight is his brilliant ear for dialogue which is given full rein in this twisted tale of allied intelligence officers, Nazis, scientists and seers united by a MacGuffin in the shape of a mysterious rocket. The action arcs from London under bombardment to a postwar zone of surrender. What is striking is how the themes explored here – forever wars, technological domination, uncontrollable cartels – have become staples of internet discourse.
Typical line 'A screaming comes across the sky. It has happened before, but there is nothing to compare it to now.'Pynchon tropes Sex, pastiche songs, real-life events
Pynchon gives the 18th-century novel a postmodern twist to explore the relationship between Charles Mason and Jeremiah Dixon, British surveyors tasked with ending a boundary dispute between the colonies of Maryland, Pennsylvania and Delaware. The Mason-Dixon line would later mark the division between free and slave states in the US.
The author layers fact over anachronistic fiction, scientific inquiry over conspiratorial rumour, and tragedy over knockabout farce, in a virtuoso display of storytelling. There are walk-on parts for Thomas Jefferson, Benjamin Franklin and George Washington. A further conceit lies in the narration of events by the Reverend Wicks Cherrycoke, many years after they supposedly took place. It is a ripping yarn spun for the incredulous enjoyment of both the cleric's family and the grateful reader.
Typical line 'For if each Star is little more a mathmatikal Point, located upon the Hemisphere of Heaven by Right Ascension and Declination, then all the Stars, taken together, tho' innumerable, must like any other set of points, in turn represent some single gigantick Equation, to the mind of God as straightforward as, say, the Equation of a Sphere, – to us unreadable, incalculable.'Pynchon tropes Pastiche songs, historical events
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