Over the past three years, I've read them all.
I flew through the earth with The Chums of Chance. I kicked through California beaches with Doc Sportello. I don't even want to begin to tell you what I did with Brigadier Pudding.
I read every single one of Thomas Pynchon's unreadable, impenetrable, chaotic-hard-right-turn novels. And when I was done, I decided to perform this service to humankind:
I'd decide once and for all which one of Pynchon's novels you should read first.
I rated every one of his eight books on four scales. Order of importance. Personal enjoyment. Accessibility. And how well it introduced Pynchon's worldview and themes.
I tallied the results nervously. What brick-of-a-book would come out on top? Melancholy dark horse Vineland? The esteemed and reviled Gravity's Rainbow? Post-9/11 mystery Bleeding Edge? Perhaps my personal favorite, the epic American meta-fiction Mason & Dixon?
Man, it wasn't close.
If you're going to read one Pynchon novel, read The Crying of Lot 49. Besides Gravity's Rainbow, it's his most famous book. It's his shortest and among the easiest to follow. And it takes you on a whirlwind trip through all his major themes. The unsettling paranoia, the layered fictions, the sad sense that maybe America had something special once, but whatever it was it's been lost and it's not coming back.
After that, read Mason & Dixon. And then just see if you can stop yourself from finishing them all. I know I couldn't.
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