Which Thomas Pynchon novel should I read first?

Answer 1

"The Crying of Lot 49." It's short & shows some of Pynchons quirks.

Good luck.

Answer 2

I would start with Vineland. I read this book first to ease myself into the glittering sinkhole that is Gravity's Rainbow. Vineland has more of a straight narrative than Gravity's Rainbow, with the absurdity still intact. When you've read a couple of Pynchon novels, pick up a copy of Slow Learner to read his early short stories and a great introduction by the author in which he openly brutalizes his own work and shows the reader how his style changed as he matured and his erudition amassed.