How to Read Thomas Pynchon

In the course of an e-mail conversation earlier this summer, I managed to convince a dear family friend (my mother’s college roommate, who bears the charming sobriquet of “Auntie Roomie”) to read some Thomas Pynchon. I believe that’s the first time I’ve ever convinced anyone to follow me down this particular rabbit hole, and I didn’t even try that hard–I wish I could remember the particular incantation that proved effective. The first thing she asked me after deciding to take up this burden was where she should start. I told her to start with The Crying of Lot 49, and have since been considering where to go from there. I think I’ve settled on the ideal path through the novels, and have embarked on it myself:

  1. The Crying of Lot 49: His second novel is the tightest (at a little over a hundred pages) and most accessible, but it still gives you a sense of the range and depth of Pynchon’s obsessions. It’s also one of only two of his novels largely set in the era during which it was written, the early 1960s in this case, and is the first of the two “Mucho” Maas novels. Having invested not too many hours in finishing this book, you’ll know for sure whether or not you’d like to continue.

  2. Vineland: A sort of sequel to The Crying of Lot 49, this is probably the least of his novels, but still quite worthy of exploration. It’s the second of the “Mucho” Maas novels, and like its predecessor, it’s set largely in the era it was written, though this time that era is the 1980s. It can also be seen as his retrospective telling of Nineteen Eighty-Four (his introduction to which is brilliant) with the unsettling twist that Big Brother proved unnecessary.

  3. Mason & Dixon: This is the chronological beginning of his alternate history (and the history of the Bodine family, which is only tangentially referred to here), though it was written late in his career. It’s a sprawling retelling of the story of the surveyors who marked the boundary line between Pennsylvania and Maryland that came to be identified with the division between North and South. Though this wasn’t written in the era that it portrays, it reads as though it was, complete with colonial American spelling, grammar, and punctuation. It’s a masterpiece in every sense.

  4. Against the Day: His last, and longest, novel to date, this is set between the 1890s and the end of the First World War. It feels very much like a thematic summation, though read in this order, it can also be seen as setting the stage for the disintegration of civilization portrayed in the next two novels in this list (and advancing the Bodine family saga, though again only in passing). By no means universally acclaimed, it is, after a couple of readings, my favorite of his novels. It seems to me to be much more a space to be inhabited than a book to be read, and I miss it when I’m not reading it.

  5. V.: His first novel, its telling mostly brackets the Second World War, with one episode set in the Siege of Malta. It brings the Bodine family more to the fore in the person of “Pig” Bodine, who will prove to be Pynchon’s Falstaff, though more like the Merry Wives of Windsor version in this case. It’s Pynchon’s first attempt to pull together his simultaneous fascinations with high and low, American and European, civilized and barbarian, comic and tragic, romantic and classical. It ultimately succeeds, and must have seemed astonishing without knowing what would follow, but subsequent attempts have been more polished and compelling.

  6. Gravity’s Rainbow: Widely considered his defining work, it is certainly the densest and most challenging of his novels. It’s set almost entirely during the Second World War, and it leaves the reader with nothing to hold on to or believe in, fully grown and facing the abyss, but it gives us the full Henry V version of “Pig” Bodine as company and exemplar. This is the novel I read first, but if I had it to do over again, it would be where I finished.

Looking this list over, I’m left wondering what the Bodine family was up to during the nineteenth century, but given the summary nature of Against the Day and Pynchon’s advanced age, I fear we won’t find out.

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