The Crying of Lot 49, Thomas Pynchon, 1966
Recommended by Harold Bloom in his classic How to Read and Why, this surrealist novel is remarkable for its humor, intricate and convoluted writing, plot structure, story, but most amazingly because though written 50 years ago, it’s all about Donald Trump and today’s America. The plot is a bit ridiculous. Oedipa Maas, a 28 year old, is named the executor of the will of one Pierce Inverarity, a onetime lover and all around narcissistic, real estate investor (sound familiar?). While investigating Inverarity’s holdings, Oedipa runs into an entire cast of weird characters and runs afoul of a world-wide conspiracy that has been underground since the 13th C, Trystero, a group intent on taking over the mail system for the world and used largely by revolutionaries (sound familiar???). Is she insane? Has Inverarity played a monumental practical joke on her? Or is she on the brink of discovering the key to a world-wide historical conspiracy? As the auction begins on Inverarity’s stamp collection in which Lot 49 holds the stamps with the clues to Trystero, the book ends without resolution. Weird, funny, and prophetic, this is an important book in 20th C. American fiction.