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Thomas Pynchon is a writer famous for having dense and hard to read books, but is acclaimed for those books. He wrote V., The Crying of Lot 49, Gravity's Rainbow, and others.

What order should I read his books? His books are often read in specific orders, because all of them are hard to understand, and some books are easier than others. What order should I read the books in to help them be easiest to understand?

closed as off-topic by user111, Rand al'Thor, Aza, Benjamin, Riker Feb 14 '17 at 2:18

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    @Valorum you can post that as an answer if you wish. – Riker Jan 23 '17 at 21:11
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    I only skim-read the link and I'm in the midst of something else. If you think it's decent, I'd suggest that you use it as the basis for a self-answer. – Valorum Jan 23 '17 at 21:49
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    I'm voting to close this question because there doesn't seem to be any connection between the different Thomas Pynchon novels. If they're not part of the same series, what could make one order better than any other? – Rand al'Thor Feb 14 '17 at 1:06
  • @Randal'Thor To match the pedant, would that not be "too broad" as reading order is specifically on-topic? – Skooba Feb 14 '17 at 21:21
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If you're tackling the first three books, I'd say Lot 49, followed by V., followed by Gravity's Rainbow. "A Journey into the Mind of Watts" makes a nice addition somewhere in there. There is a serious ramp-up in difficulty across those three books:

  • Lot 49 is slender and doesn't require too much prior knowledge to follow what's happening or why something is important. There are scenes where characters are hallucinating, but it is easy for the reader to determine when this is happening.
  • V. is long, but most chapters are self-contained episodes -- or seem to be, until the overall pattern emerges. One character under extreme psychological stress hallucinates, but it's obvious to the reader. Features a few characters who show up once for some gag purpose, only to disappear forever, which is good practice for GR.
  • Gravity's Rainbow is incredibly long and dense. A good "prior reading" list would probably include at least excerpts from more than 20 books. Pynchon moves from reference to reference faster and more often than a Simpsons episode, and the range of things being referenced is incredibly broad. The narrator tries to be helpful, but is hampered by the fact that not only are many characters dreaming, hallucinating, or undergoing extreme psychological stress, but the author himself may have been doing any or all of those things whilst writing.

Vineland might make a good alternative starting place (or Lot 49 --> Vineland). Similar level of length and difficulty to V.. Might seem relevant if you follow American politics. Good introduction to both the first and the second half of his career.

As for whether a reader will "miss out" on critical information if they haven't read Book A before Book B, generally, no. There are a number of "soft" connections between the books, i.e characters who played a large role in book A showing up for a cameo in book B (e.g. Mucho Maas from Lot 49 shows up briefly in Vineland, Pig Bodine from V. shows up in a bunch of places). A major exception to this -- a "hard" connection -- is the Suedwest Africa chapter of V. introducing characters, historical background, and themes that are all explored much more extensively in GR. Due to V.'s episodic structure, that chapter can be read as an excerpt if a reader is trying to "short cut" to GR but still get as much background as possible.

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(Admittedly, this advice is contrary to what most people say on the subject - Kevin Troy's answer has the standard advice covered very nicely - but I'll give my answer nonetheless. If it's not useful to you you'll be no worse off, but on the off chance it is, well, here you go:)

My advice would be to start with Gravity's Rainbow. Why? Because it's the one people talk about in hushed tones, the one people put off reading for fear they aren't up to the task.

But it's just a book. It's a strange book, sure, but it's far from the impenetrable thing people make it out to be. It possibly seems that to people who take it too seriously, who think everything in it must be a reference to something else, and every scene and character is part of some larger whole beyond their comprehension. Now, there are a lot of references to other things - sure - and deeper meanings to be found if you search for them - yeah, and some of it's pretty cool - but I also think Pynchon gets overanalysed. I suspect he's just having fun a lot of the time, and a lot of it isn't really supposed to make sense on any kind of complex level.

Relax, just let it happen, accept you aren't going to be able to keep track of it all, and it's not so difficult.

After you've read Gravity's Rainbow, I'd suggest Vineland as your next stop. Why? Well because it's just so not Gravity's Rainbow. Where Gravity's Rainbow is long, fast-paced, complex, and deals with characters lost in the chaos of the wider world, Vineland is comparatively slow and gentle, and deals more intimately with individuals. Its characters feel more real, and the world they inhabit - though still strange - feels more like our own.

I think once you've read these two, the order of your remaining reading won't matter too much. You'll have a good feel for the spectrum of emotions that Pynchon likes to take his readers through, and hopefully you'll have developed a taste for it, too. If so, pick one at random, or one you like the sound of, and read on.

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