1. Underworld by Don DeLillo
![Underworld by Don DeLillo Underworld by Don DeLillo](https://media.timeout.com/images/102912074/750/422/image.jpg)
![Underworld by Don DeLillo Underworld by Don DeLillo](https://media.timeout.com/images/102912074/750/562/image.jpg)
Mammoth and sweeping, DeLillo’s brick of a book proffers a kaleidoscopic view of the city and the nation, as each clatters through the second half of the 20th century and the Cold War. Though the central story involves an affair between waste management exec Nick Shay and artist Klara Sax, DeLillo steps into the shoes of a multitude of characters—among them, J. Edgar Hoover and Lenny Bruce. Like New York itself, the 800-page Underworld is fiercely ambitious, messy, multifarious and while it seems overwhelming at a distance, its rich details and worlds within worlds prove endlessly enriching up close.