What does it mean to know a city? Without a doubt, you need to have lived in it. You need to have walked its streets, explored its parks and waterways; you should eat in its restaurants, feel invested in its institutions, both large and small. You need not have visited every corner of it, perhaps, but you need to know of their existence. But even if you do all this, you might still be missing the larger context of a place, an awareness of its history, its triumphs and troubles. And so there’s no better place to turn than to its books.
New York is lucky in this way; there are few other places with such a rich literary tradition, such a strong association with the written word. It’s possible to gain intimate knowledge of this city of ours by reading your way through its centuries. But where to start? The following 100 works—a healthy mixture of fiction and non-, with a few poems, plays, and essays sprinkled in for good measure—are listed roughly in the chronological order in which they take place. Read straight through the list and you’ll travel from New Amsterdam to the edges of our gentrified metropolis. Read all these selections, or read just one; just know that each of these works has the ability to make non- and native-New Yorkers alike (or even those who have never so much as visited) feel that they are not just living in this city, but are truly of it, and help them to better understand this place they call home.
1. The Island at the Center of the World
This fascinating historical narrative demonstrates why New York is a city unlike any other in America. (Spoiler: It’s because it started out Dutch, not Puritanical and English.) Also, you get to find out all about who Peter Stuyvesant was and why so many derivations of Dutch words are in the New York vernacular.
2. Leaves of Grass
Containing what is perhaps the sexiest author photo ever (Whitman was quite a looker; it is not the same picture that you see on the cover to the left of this blurb BY THE WAY), this poetry book is seductively brilliant and far ahead of its time. It’s also responsible for the oft-quoted phrase “I contain multitudes,” which has been bastardized to describe a whole number of things, always to great effect. I’m sure Whitman would have approved. He seems like a pretty chill dude.
3. The Gangs of New York: An Informal History of the Underworld
Easily one of the most fascinating, if ugliest, times of New York City history, the mid-19th century was full of shocking violence, nativist sentiment, corrupt politicians, and truly colorful characters. Asbury shines a light on some of the grimiest parts of New York’s past.
4. Paradise Alley
This pitch-perfectly rendered look at Civil War-era New York illustrates some essential, if nearly forgotten, parts of New York’s history, like the 1863 Draft Riots and the founding of Central Park, and it resonates all the more deeply due to the ongoing inequality issues we face today.
5. Low Life: Lures and Snares of Old New York
Sante makes the incredibly difficult task of writing entertainingly about mundane subjects like a city’s topography look easy. He also manages to elucidate some of the most profoundly dark times of New York’s history, and is never afraid to get down into the gritty underside of the city.
6. Washington Square
This slim novel might be set almost 150 years ago, but it’s central question (basically, where is love?) is as relevant—and its answer as complicatedly depressing—now, in the age of Tinder—as it was back then.
7. Martin Dressler: A Tale of an American Dreamer
Millhauser’s foray into magical realism is Borges-ian in its use of architecture-as-metaphor, a technique that has perhaps never been as apropos as when used with regards to New York City, where our buildings are also, like, ourselves.
8. Gotham: A History of New York City to 1898
This Pulitzer Prize-winning tome is as compellingly written as any straight history book we’ve ever had the pleasure of encountering. It’s an entertaining look at the city before the Great Mistake of ’98.
Houdini! Evelyn Nesbit! Booker T. Washington! Emma Goldman! This historical novel manages to cram in just about every fascinating character of early 20th century New York and its narrative is as rollicking and lively as the best ragtime songs.
10. Call It Sleep
Roth takes readers through the coming-of-age version of a young Jewish boy on the Lower East Side, who is grappling with issues of identity, family, and belonging. The historical context is fascinating, and the sentiments it evokes are timeless.
11. The Museum of Extraordinary Things
This magical novel takes readers back to turn of the century Coney Island freak shows—complete with mermaids!—as well as darker historical events like the Triangle Shirtwaist Factory fire, all through the perspective of a young woman falling in love for the first time. It’s a romanticized view of that period of New York history, to be sure, but sometimes, a little romance goes a long way.
12. All-of-a-Kind Family
So, I don’t know about you, but here’s what I’m interested in when it comes to stories of how people used to live: their food, their clothes, and how many people slept in a bed. And guess what? That’s exactly the kind of thing you find out in this incomparable series of children’s books. You get to read to your heart’s delight about ha’penny candy, tea-stained crinoline, swapping sugar for salt in the Sabbath’s gefilte fish recipe, and the pleasures and traumas of sharing a bed with your sister. It’s all a too, too perfect vision of tenement life on the Lower East Side circa 100 years ago.
13. A Tree Grows in Brooklyn
Do I really need to sell you on this classic? I don’t know. Maybe? Well, here you go: Smith manages to unsentimentally portray the hardscrabble life of the Nolan family in pre-bridge Williamsburg in a totally compelling manner, making it impossible for readers young and old not to murmur I’ve been there! every time Francie makes passing mention of a north Brooklyn landmark. This is an essential read for anyone who wants to feel like they really belong in this city of ours.
14. The Age of Innocence
It’s so hard to select just one Wharton novel for this list (but, side note, I was determined to have no more than one selection per author for this list), and while The House of Mirth is probably my favorite Wharton, thanks to Lily Bart and those bracelet manacles she bears, The Age of Innocence could not be a more perfect rendition of the pressures put upon women in New York society so many years ago. Luckily, now, everything is perfect for women in New York and there’s absolutely no external pressures to be a “perfect” wife and mother in our modern day and age. Luckily.
15. The Beautiful and Damned
While The Great Gatsby is obviously Fitzgerald’s most famous New York novel (and just most famous novel in general) The Beautiful and Damned is nonetheless an inescapably provocative look at what happens when young New Yorkers live fast and crash hard. It’s absolutely worth a close read for every young person who can’t quite imagine that the party will ever end.
16. Saint Mazie
Inspired by the larger-than-life character Mazie Phillips from Joseph Mitchell’s Up in the Old Hotel (see: #30), Attenberg takes readers on a tour of Jazz Age and Prohibition-era New York, which would be interesting enough in her adept hands, but is made all the more rollicking of a journey thanks to the fact that our real guide is none other than the bawdy, irrepressible Saint Mazie herself.
17. Home to Harlem
A central literary figure of the Harlem Renaissance, Claude McKay’s Home to Harlem depicts the divergent lives of two young black men whose vastly different pasts have led them to the same place and time—post World War I-Harlem. It’s a fascinating look at the decadent, hedonistic lifestyle, full of dizzying highs and catastrophic lows, of the era.
18. A Walker in the City
Kazin recounts his Brownsville childhood in this memoir, and beautifully evokes what it was to grow up in this once heavily Jewish part of Brooklyn during the early years of the Great Depression. And as was the case for so many other Brooklynites at the time (and for decades after) the future and all the hope that comes with it are all centered around one magical, mythic place: Manhattan.
Easily one of my favorite books on this whole list, Passing is a provocative exploration of identity and race and class and womanhood and friendship and, oh god, everything that matters in life, i.e. everything worth fighting about and worrying over. Larsen brilliantly depicts deeply flawed and complex women who don’t quite know how best to make their way through a society that doesn’t really have a place for them, which leads them to, at times, take some pretty drastic measures just in order to survive. If you’re going to read only one book on this list, maybe make it this one. There’s nothing else quite like it.
Morrison experimented with form in this book, and her words evoke the call-and-response technique utilized in the genre of music upon which she centers this novel: death metal. Just kidding! It’s jazz. Even if you’re not that into jazz (and maybe that’s just because you haven’t heard it in the right venue?), the multiple narrators and Morrison’s quickly shifting story line keep readers constantly engaged and in awe of her virtuosic powers.
This flat-out magical book is told from two different perspectives and depicts two, decades-apart versions of New York which wind up colliding in a beautifully unexpected manner. Along the way, Selznick affords readers an intimate, seemingly behind-the-scenes look at New York institutions ranging from the American Museum of Natural History, the city panorama at the Queens Museum of Art, and a lovely, if apocryphal independent bookstore.
22. The Blacker the Berry
An essential read about the struggles of a black woman seeking to find her place in a world that’s turned against her, The Blacker the Berry explores the nuances of racism and sexism and the intersection at which they meet in an effort to show one woman’s path to self-acceptance. Set against the backdrop of the Harlem Renaissance, the novel also affords readers a look into what was a rapidly changing world, one which (appeared to, at least) finally gave marginalized people the opportunity to escape their societally imposed restrictions.
23. The Group
Any book that was banned in Australia is alright with me, but The Group is especially alright because it is full of strong women and strong politics and strong sexuality and while it is set in the 1930s and was written in the 1960s, it feels pretty damned relevant to the 2010s. if you ask me. Besides, who doesn’t want yet another reminder that women have been looking for ways to subvert the patriarchy throughout history?
24. Daddy Was a Number Runner
This is a beautiful, searing novel told through the perspective of a young girl growing up in Harlem in the 1930s, and who struggles with the realities of life in that time and place in a way that is heart-breakingly familiar and thankfully devoid of any trite sentimentality. Daddy Was a Number Runner‘s protagonist Francie Coffin is also an interesting match to A Tree Grows in Brooklyn’s protagonist Francie Nolan, and I’d recommend reading the books one after the other.
25. The Power Broker: Robert Moses and the Fall of New York
Hey, ever wonder why Red Hook is so isolated from the rest of South Brooklyn? Or why there’s a big old highway breaking one part of Williamsburg apart from the other? Ever just stop and think about why New York is so car-friendly at all? Stop racking your brain and pick up Caro’s masterwork about one of the most powerful—and powerfully reviled—figures in this city’s long, complicated history.
26. The Amazing Adventures of Kavalier and Klay
An adventure-filled narrative loosely based on the real life-stories of many of the creators of comic book creators like Jack Kirby and Stan Lee, and is filled with cameos by historical figures including former New York governor Al Smith and artist Salvador Dali, Kavalier and Klay depicts a fascinating time of New York history and is a testament to the ingenuity of this city’s (and country’s) immigrant communities.
27. Brooklyn Is: Southeast of the Island: A Travel Guide
Agee’s meditation on Brooklyn remains one of the most beautifully rendered depiction of this—or any—part of the city we like to call home. Last year, we wrote extensively about this work, calling it “a lyrical, wandering essay of observational prose” and we can’t recommend highly enough that you spend some time with this slim volume, and fall in love all over again with Brooklyn.
28. The Chosen
Potok takes us deep into a community that remains closed off and mysterious to so many of us, despite its very visible presence on the streets of this city. Via the perspectives of Reuven Malter and Daniel Saunders, the reader gets a chance to experience the inscrutable world of ultra-orthodox Judaism.
29. Sophie’s Choice
The part of this novel that everyone remembers tends to be the one that occurs far from New York City, and yet it is the city-based parts of the book that are the most compellingly rendered, I think. Styron is never better than when he depicts what it’s like to be a struggling, frustrated young writer who is forced to live in deep Brooklyn due to rent considerations and finds himself sexually thwarted at every turn until he—suddenly, gloriously, disastrously—isn’t.
30. Up in the Old Hotel
Initially published in The New Yorker, Mitchell’s collection of essays are wonderfully rendered depictions of classic New York characters—saloon-keeps, sailors, Native American construction workers, street-preachers—all of whom will be welcome additions into your life as they were into the lives of old New Yorkers.
31. A Drinking Life: A Memoir
Hamill’s autobiography brings readers back to a Brooklyn that was still filled with trolley cars, where the Dodgers were local heroes while still never not being bums, and where beer could be consumed by the buckets in male-only Irish bars. It’s a Brooklyn that, for better or worse, doesn’t exist anymore, but one that’s absolutely worth revisiting via Hamill’s smart, spare prose.
32. The Street
Petry’s novel centers around a black single mother in Harlem who is doing the best she can to raise her young son and gets thwarted by, ahem, total assholes at every single turn. Petry doesn’t pull any punches here, it’s impossible to read this and not spend some time afterward thinking about how full of trials and tribulations so many women’s lives are, and how there’s pretty much nobody willing to help them who isn’t also—or only—looking to help themselves. There is no happy ending here, by the way. It ends the only way it can: in heart-break.
33. Here Is New York
White’s love letter to New York is always worth a re-read, singular as it is in its ability to make you forget all the bullshit that exists in your quotidian city life and appreciate the complicated beauty that surrounds us in our metropolis.
34. El Bronx Remembered
This short story collection tells a variety of stories about a borough that doesn’t ever get enough attention paid it, other than when the Yankees are doing particularly well. Mohr’s characters are vividly rendered and she beautifully depicts how the Bronx transitioned from a predominantly Jewish stronghold into a primarily Puerto Rican one over the course of a few, tumultuous years.
35. Montage of a Dream Deferred
Comprising almost 100 poems that are meant to be read as one long poetic meditation on black life in New York, Montage of a Dream Deferred is not only essential reading for anyone hoping to gain insight into the black experience during that time in New York—and America—but also can be read as a cry for social justice that transcends the era and place in which it was written.
36. Invisible Man
Ellison’s masterpiece is, simply put, one of the most profoundly moving, tragi-comic works of the entire 20th century. The unnamed narrator’s journey through politically and socially roiling Harlem as he struggles to figure out his place in the world is one of the most affecting meditations on identity and race ever written.
37. The Bell Jar
Although the majority of Plath’s novel doesn’t take place in New York City, the parts that do take place during an electrically charged summer, and Plath beautifully captures what it means to be a woman who is young and free (which is to say, still impossibly burdened) and on her own in New York for the first time.
38. Brown Girl Brownstones
Marshall depicts the lives of a family of Bajan immigrants who come to Brooklyn in the mid-20th century in vivid prose, inviting us into the race- and class-based struggles that they find themselves dealing with in their new home. Marshall is particularly effective at portraying what it’s like to be a reluctant immigrant here, and how that fight to retain identity informs so many other parts of the transition to becoming an American.
39. Franny and Zooey
Yeah, yeah, The Catcher in the Rye is the obvious Salinger choice, but what’s more New York, really, than a character who spends hour upon hour reading in the bathtub while simultaneously chain-smoking? Nothing, really. Other than that he has a sister who only eats cheeseburgers. We all have one of those, right?
40. The Mambo Kings Play Songs of Love
The story of New York—like the story of America—is the story of immigrants, and rarely has it been rendered as evocatively as by Hijuelos in his Pulitzer Prize-winning book about two Cuban brothers who come to New York to play music and build a life.
Toíbín’s novel (now a movie!) is a compelling depiction of the life and loves of a young Irish woman who keeps thinking she has found her place in a confusing world, until she finds out she hasn’t. Is it yet another book on this list that grapples with issues of place and identity and the struggle to find out where we really belong? Why, yes. Yes, it is. Welcome to New York. It’s been waiting for you.
42. When I was Puerto Rican
This autobiography tells the story of Santiago’s move as a child from a barrio in Puerto Rico to the streets of Brooklyn. Santiago is relentlessly engaging, even—or especially—as she details what would seem like the insurmountable difficulties of moving to a new country with a new language and not so much in the way of money.
43. Another Country
Set in Greenwich Village in the 1950s, Baldwin vividly portrays issues that might be familiar today—fluid sexuality, interracial relationships—but that were totally taboo when the book was published. Oh, well. Times have changed, but it remains true that Baldwin’s ability to shock—both with his subject matter and his beautiful prose—continues today.
44. Breakfast at Tiffany’s
First: Don’t watch the movie! I don’t care how great Audrey Hepburn is in it (which, very), because the atrocity that is Mickey Rooney renders the film unforgivable. But… read the book. Capote does an amazing job of capturing the ultimate new-to-New York experience of whole-sale recreating yourself in an effort to totally shed your less-than-stellar past life. Oh, and also: prostituting yourself. That is very New York.
45. The Inferno (A Poet’s Novel)
This roving, roaming book is Myles at her finest (though, really, when is she ever not?) and takes readers on a deep dive into the raucous mess that New York was for Myles, certainly, when she was young (and, no, this isn’t technically autobiography, but also, don’t be blind), but which also holds true for all of us, pretty much, who are in New York when we’re young.
46. The Basketball Diaries
Who doesn’t love a good coming-of-age story? Especially one set in New York. Especially one that isn’t “good” exactly, but is also, kind of, bad, and therefore the best. Anyway, that’s what The Basketball Diaries is; it’s raw and drug-fueled and teeters on the edge of insanity, tempting you to fall off that edge, clutching this narrative on your way down, knowing as you’re falling that it’ll be a long climb back up.
47. Lunch Poems
What is it like to take a lunch hour in a city that’s not as walkable as New York? I have no idea and I never want to know. I’m so grateful for the ability to walk a few blocks every day, see the shifting faces of all the people walking by, imagining having conversations with them. It’s this experience that O’Hara captures so beautifully in Lunch Poems, each poem gives a perfect peek into his head as he perambulates the city streets, pausing to think about and then share with us whatever happens to cross his mind.
48. Dreaming in Cuban
Garcia’s epic tale centers around multiple generations of an exiled Cuban family, revealing a lot about the lives of not only first-, but also second- and third-generation immigrants, making clear how disparate the lives are of all of us who call New York home.
This short play takes place only on a subway, and is as hellish a voyage as its subterranean setting would suggest. Baraka provocatively grapples with issues of race and sex on a biblical scale; yes, an apple is involved. All I’m saying is, the next time you’re set to complain about your commute, stop and read Dutchman instead.
50. The Bridge
Say “the bridge” and most people in New York will think you’re referencing the Brooklyn. But read The Bridge and realize that the coolest span in the five boroughs (and the longest suspension bridge in the world) is the Verrazano, which is here rendered in a style befitting its larger than life scale by the wonderful Gay Talese.