The best books for diving deep into the dark side of Brooklyn

Displaying the decaying carcass of post-war South Brooklyn, Hubert Selby Jr. mines a grim industrial wasteland, as bleak as his beleaguered characters imploding across six short stories, each prefaced by a Biblical passage.

A gang mauls a group of soldiers on leave. A transgender woman, abused by a homophobic brother, rejected by a drug dealer, overdoses. Facing a shotgun wedding, a young man abandons his pregnant girlfriend. A sex worker is gang raped to death. A corrupt, closeted union steward is severely beaten after sexually assaulting a boy.

This 1950s South Brooklyn, when the Brooklyn Army Terminal complex and waterfront docks were infested by racketeers and thugs, comes to brutal life because of Selby’s crude prose. That grammar-be-damned style vividly captures Brooklyn life on the docks, factories, and warehouses, as well as its diners, dive bars, and union locals.

Love to know why this murderous mob masterpiece has yet to make it to film.

This must-have for any True Crime bookshelf is from the dynamic duo of Gene Mustain (author of John Gotti bio) and Jerry Capeci (“Gangland” journalist extraordinaire). It chronicles the blood-soaked rise and demise of the deadly Roy Demeo crew, a gaggle of Gambino grunts a couple of rungs under Captain Nino Gaggi.

It’s an underworld tour of the black-and-blue-collar South Brooklyn rackets, circa 70s and 80s, often through the bloodshot eyes of Dominick Montiglio, Gaggi’s nephew, and bolstered by an avalanche of investigative research. From the innards of a Mafia street crew, to the entrails of an auto-theft ring, to the autopsy of Demeo’s whack-tastic dismemberment routine (a.k,a. “The Gemini Method”), there’s so much to digest, if you can stomach the body count.

Locations of interest: The Gemini Lounge on Flatlands Avenue; Bath Beach (Multiple Locations); Veteran’s and Friends Social Club on 86th Street; The Fountain Avenue Dump; Varuna Boat Club in Sheepshead Bay; Holy Cross Cemetery

In adapting Nicholas Pileggi’s 1985 non-fiction Wiseguy for film, Martin Scorsese delivered a “staged documentary,” depicting a far more gritty and authentic account of organized crime than Mario Puzo’s Godfather trilogy.

Much of what makes Pileggi’s masterpiece work is how he captures South Brooklyn culture as it morphs from the 1950s through the 1980s. Pileggi’s tale of the tarnishing of the Golden Era of Italian American organized crime is recounted from the pedestrian perspective of un-makeable underling and ultimate-turncoat Henry Hill.

That bygone Brooklyn landscape leaps off the pages, from its gambling dens and gangster bars, to its corner cafes, criminal courts, and cab stands. BONUS: Pileggi’s no-nonsense non-fiction prose, peppered with Hill’s verbatim account, delivers even more days-in-the-lives of lowlifes than Scorsese could ever have packed into his classic film. 

Locations of interest: The Prospect Park Zoo (stand-in for The Tampa Zoo); Smith Street in Red Hook (Jimmy Conway’s Sweatshop); The Oriental Manor on 86th Street (Henry and Karen’s Wedding Scene); Collaros Italiano Restaurant on  Coney Island Avenue (Exterior for the Bamboo Lounge).

Donnie Brasco follows FBI agent Joseph D. Pistone’s six-year infiltration into the Mafia.

Posing as a street-level jewel thief, Pistone provides a bottoms-up look into the underbelly of the Brooklyn Bonanno’s in Brooklyn, from the family’s epicenter in pre-gentrified Williamsburg and Greenpoint. This rank-and-file rundown shines a harsh light on the petty lives of street soldiers and their conniving capos in their natural habitat, from scrounging for scraps in wood-paneled clubhouses to lording over their turf from pigeon-cooped rooftops.

In fact, the juxtaposition of setting, in flipping between sinister South Brooklyn and sizzling South Florida, is a masterful use of setting to set the tone. As Pistone goes native, becoming more and more Bonanno, we wonder what he sees in The Life led in these cramped apartments, velour-draped dives, and dingy clubhouses.

Locations of interest: The Motion Lounge nightclub on Graham Avenue in Williamsburg; Brooklyn Armory in Park Slope; The 20/20 Night Club in Clinton Hill (Site of The Three Capos Murder).

Hubert Selby Jr. delivers another dark indictment of life along the outer shores of South Brooklyn, in the form of both this 1978 novel and the grim 2000 film Darren Aronofsky film adaptation (co-written with Selby, with a cameo as prison guard).

The characters of this disturbing drama are as marginalized as the bleak 1970s backdrop they infect. Selby’s prose holds us by the back of the neck as his characters descend down awful spirals of addiction: Sara Goldfarb with her diet pills, and her son Harry, his girlfriend Marion, and his best friend Tyrone, all heroin addicts. Electroconvulsive therapy, reluctant prostitution, and amputation abound, harrowing hallmarks you’d expect from Selby.

For this trip to Coney Island, think more Warriors, less Woody Allen, and buckle up. It’s going to be a spectacularly gruesome ride.

Locations of interest: Coney Island Clam Bar; Brighton Beach Boardwalk; Surf Avenue Second-hand Shops; 3152 Brighton 6th Street Apartment; Pat Auletta Steeplechase Pier; The Parachute Jump.