The Friends of Eddie Coyle may be one of the most influential neo-noirs of the 20th century. The titular Eddie Coyle is a small time gunrunner and mob affiliate facing a few years of Federal prison time. Aside from his career, he's basically a middle class guy, and he doesn't want to spend a couple years on ice away from his wife and kids. The only way out is to give the cops enough evidence on someone more interesting to get his bootlegging charges dropped. Meanwhile, other small time hoods are running their own schemes: selling machine guns to political radicals, robbing banks, and running a bar/mafia answer service, all under the knowledge that any of them might turn rat.

The story unfolds through looping, discursive, incredibly realistic dialog. These are guys with a lot of street smarts and not a lot of wisdom, trying to put together their deals, feel out the other side, and mostly gripe about their lot in life. Nobody including the cops, who are just another set of crime adjacent working stiffs, has anything approaching the whole picture.

Just a gorgeously bleak and cynical book.