Thomas Pynchon isn't exactly the most prolific author on the planet, but his output is still pretty daunting in its sheer weight and complexity. So Vulture has done the world a service, by ranking every Pynchon book from worst (Against The Day) to best (The Crying of Lot 49).
They make a strong case for the relatively slim Lot 49 being both his best book, and his most accessible to new readers. But they also make a really great argument for their #2 pick, Gravity's Rainbow, saying:
Gravity's Rainbow stands comfortably between Herman Melville's Moby-Dick and David Foster Wallace's Infinite Jest as the type of large, American book that true fans will read and reread to see what they missed the first time around. The co-winner for the 1974 U.S. National Book Award for Fiction (along with A Crown of Feathers and Other Stories by Isaac Bashevis Singer) sits at the top of the mountain of paranoid, postwar/Cold War masterpieces (along the lines of works by Joseph Heller, Kurt Vonnegut, Rudolph Wurlitzer, and Don DeLillo) that helped us visualize the senselessness that is war.
Check out the whole list, and the rationales, over at the link. [Vulture]