The Worm in the Big Apple: Seedy New York City Stories

For most of my 20s, I worked a few blocks from Wall Street in Manhattan. I rode the subway with people who were going off to do mysterious things with money and also with the people who went to work in the coffee shops and restaurants that kept those people fed. There are as many New Yorks as there are New Yorkers. From walled private gardens to the street that was home to the gangs of New York, this selection of seedy New York City stories will show you just a few of them, past and present, real and imagined. Some of them will take you into a world that is darker than you imagined—and some of them will bring you back into the light, letting you see New York City in all of its beautiful contradictions.

Cover: The Bowery by Stephen Paul DeVillo

The Bowery: The Strange History of New York’s Oldest Street by Stephen Paul DeVillo

The Bowery is New York’s oldest street as well as being Manhattan’s broadest boulevard. It has played host to saloons, freak shows, gangs, and some of the worst New York has offer—as well as some of its best. It was the site of New Amsterdam’s first murder and legendary music club CBGB. P.T. Barnum got his start there. Harry Houdini played the music hall and dime museums.  DeVillo postulates that The Bowery reflects the history of the city that grew up around it. 

Free Food for Millionaires by Min Jin Lee

Casey Han is the Princeton-educated daughter of Korean immigrants, navigating a glamorous Manhattan lifestyle she can’t afford. She is determined to make it on her own, despite her credit card debt and toxic boyfriend. An encounter with an old friend introduces her to an opportunity that would solve many of her problems—but at what cost? This book takes you into the world of bankers and of millionaires, in search of the kind of handouts that people in real poverty would scorn.

The Flamethrowers by Rachel Kushner

Set in New York City and Italy in 1975, a young woman called Reno has come to New York determined to become an artist. She inhabits a SoHo that has blurred the lines between life and art. She meets an artist named Sandro Valera, who is the son of an Italian tire and motorcycle empire. During a visit to his family home in Italy, she becomes entangled with members of another radical movement. 

Cover: The Golden House by Salman Rushdie

The Golden House by Salman Rushdie 

In a city where money is power, René, a young filmmaker, spies on his neighbor, Nero Golden. Golden’s improbable name, mysterious origin, and three unusual adult sons are the subject of much speculation in “the Gardens,” a cloistered community within Greenwich Village. Who gets to “belong” in a city where money equals power? René finds his way into the family’s quarrels, infidelities, and crimes. At the same time, a presidential candidate referred to only as “the Joker” begins to rise, turning New York upside-down.

Sweetbitter by Stephanie Danler

Tess, 22, is a “backwaiter” at an upscale Manhattan restaurant. Stephanie Danler takes us into a world of high cuisine and cocaine, fine dining and dive bars. As part of an education that could only be provided by the restaurant industry, Tess becomes drawn into a strange love triangle and experiences all of the brutality, fragility and beauty of being a young woman in New York. This book has also been adapted into a TV series for Showtime. 

Zone One by Colson Whitehead cover

Zone One by Colson Whitehead

In a post-apocalyptic horror novel that may hit a little close to home these days, a pandemic has devastated the planet and sorted humanity into the infected and the uninfected. The infected are the living dead. As the plague begins to recede, Manhattan must be resettled. Civilian teams working in lower Manhattan work on clearing out the “malfunctioning” infected, catatonic and transfixed by their old lives. Mark Spitz, a man working for one of the civilian teams, reflects on his survival during the outbreak and how to come to grips with a changed world. 

Inferno by Eileen Myles

Myles tells the story of the squalor and, conversely, the loveliness of being a young poet in New York during its punk heyday. The unusual voice and structure of the work adds to the feeling that we are discovering ourselves right alongside the heroine and the dog she adopts off the street. Also, how often do we get the portrait of the artist as not a young man?  

Cover: Machine Made by Terry Golway

Machine Made: Tammany Hall and the Creation of Modern American Politics by Terry Golway

Tammany Hall was New York’s most famous political machine and William “Boss” Tweed its most infamous crook, synonymous with the seediest kind of New York politics. But is there more to this story? Golway dismantles the stereotypes of Tammany’s very real corruption to reveal its forgotten role in protecting marginalized Irish immigrants in a time when power belonged to an elite Protestant merchant class. In this book, Tammany’s ugly history is not ignored but the author shows how it also laid the groundwork for social reform. 

The City We Became by N.K. Jemisin

The greatest cities, after hundreds of years or more, are born into a sort of life. It is New York’s turn and six avatars, one for each borough and one for the city as a whole, need to protect it after its birth goes awry. This novel uses all of the best and worst things that make New York unique among cities to fight back against an ancient evil that would see to it that it is never born at all. This is the first book in a trilogy.


Do you have a favorite New York story (whether it’s “seedy” or not)? Tell us about it on Facebook or Twitter! In the meantime, here are some more of our favorite women’s coming of age tales set in NYC and a Big Apple list for the kiddos, too.