Where should I start with Thomas Pynchon?

“The crying of lot 49” for sure. Difficult reading but a good intro.

The Crying of Lot 49 might be the best introduction to Pynchon and his concerns, i.e. his themes and the paranoia that characterizes everything he writes. It’s also pretty funny at times, but the prose is not as strong here as in his subsequent novels.

An easier introduction but one less characteristic of Pynchon’s other work would be his most recent novel, Inherent Vice. This is an awesome trailer for that book. Pynchon is narrating.

I personally began with Gravity’s Rainbow and then went to The Crying of Lot 49, then to Inherent Vice (because it happened to be released that summer) and Against the Day. It worked out fine.

My only advice is that you probably shouldn’t begin with Mason & Dixon, great as it is; it’s longer and stylistically more difficult than even Gravity’s Rainbow. And for the record, Against the Day was great but not able to hold my attention the way his other stuff has.

V. is another option, but I haven’t read it yet and can’t help you there.

@hawaii_jake will be able to help more once he see this question.

I know he’s famous and all, and very reclusive, but I couldn’t get anywhere with Gravity’s Rainbow. Perhaps I was foolish to start, or too young. I had it sitting on my shelf and I’d take it down and work on it for a while, then put it down, and this happened any number of times before I put it back on it’s shelf and let it fester.

He and James Joyce. Utterly defeat me.

Well, until fluther dies, I may never read another novel again. But if it does die, I might try Pynchon again. See if I’ve learned anything over the last thirty years or so.

@absalom is right to recommend starting with The Crying of Lot 49. It is full of the weird angst and quirky paranoia that Pynchon is so good at. He names his characters insanely, and uses sentences that circle back on themselves. It’s a romp.

Gravity’s Rainbow is the book he’s best known for since it won the National Book Award, but it’s not the one to start with. First of all, it’s too long for an introductory read. Secondly, the ideas presented in it really start with The Crying of Lot 49 and V.

A lot of people have trouble with Pynchon. I recommend setting aside everything you’ve ever read or studied about what a book should be when you pick up one of his. If you’re having trouble with a particular sentence, you can bet that he wanted you to have trouble with it, because he wanted you to read it over and over.