The Crying of Lot 49 (1966)

The Crying of Lot 49
by Thomas Pynchon
(1966)

The shortest of Pynchon's novels is also his most accessible — but that doesn't mean it's all that accessible. I probably read this for the first time when I was 13, and I think I only really understood everything after I read it for the seventh time, in my mid-20s. Pynchon's writing is obscure, difficult, profane, hilarious, and haunting. On the surface, a story about a woman (Oedipa Maas) being appointed executor of the will of a rich ex-boyfriend (Pierce Inverarity) sounds like it could be the start of an interesting mystery. And it is. But what she uncovers is so satisfying in its implications that you might find yourself getting a tattoo of a certain symbol in the book. Few tattoos would announce your lit-nerd cred as loudly as the muted post horn. As my friend Nathan gave the tattoo to my ex-girlfriend Liz when they were in high school, he said "not very many people will know what this means, but the people who do will fall in love with you for having it."

But be prepared for some passages that are difficult to parse. Take the book one paragraph at a time. Or one sentence at a time. As for help if you get stuck — read difficult passages out loud with a friend until you get it. It's worth the effort.