What to say about New York? As both a place and an idea, it’s too big to be summed up or even fully known. But that hasn’t stopped countless writers from trying, often via fiction — which, like the city, lends itself to wandering. If anything, New York’s scale and complexity — the diversity of neighborhoods and industries and lives that coexist here — are what make it an inexhaustible and consistently compelling setting. There’s also the fact that it’s so closely associated with ambition, which, as any storyteller will confirm, tends to be a useful thing for a protagonist to have. And so, despite myriad differences in aims and style, the New York City novel has become its own literary category, one that T explored for this project, which compiles what we’ve deemed to be the 25 most influential New York novels published between 1921 and 2021.
To make the list, we assembled a panel of judges — the novelists Katie Kitamura and Michael Cunningham, the bookseller Miriam Chotiner-Gardner (who works at the quintessential New York bookstore Three Lives & Company in Manhattan’s Greenwich Village), the playwright and television writer Branden Jacobs-Jenkins and the journalist Mark Harris. Each of them nominated 10 or so books he or she felt strongly about. Then, on a Friday in February, they met up to debate which titles should be included in the final version. These sorts of lists always come with caveats, the most obvious in this case being that this was a deeply subjective exercise shaped by reading histories and preferences. There wasn’t always a consensus about what was worthy and, though there were some undisputed favorites, we didn’t even attempt to rank the books — instead, they appear more or less in the order they did in conversation. In some cases, suggested titles simply didn’t fit the criteria — Edith Wharton’s best-known novels (“The House of Mirth,” 1905; “The Age of Innocence,” 1920) just missed the temporal cutoff, for instance, and we decided that Gatsby was really more of a Long Island man. (The group also agreed not to consider anything written by the panelists themselves or by T’s editor in chief, Hanya Yanagihara.)
When he first heard about the assignment, Cunningham wisely asked whether most New York novels couldn’t just as easily have been set in another city. Upon reflection, though, we agreed that there are certain books you can’t quite imagine taking place anywhere but here, in which New York becomes a character all its own. — Kate Guadagnino
Kate Guadagnino: To start with the most obvious question: What is a New York novel?
Mark Harris: I was looking for something that either reflected an aspect of the city that I recognized or showed me a city I didn’t recognize — but that I learned through reading was part of its DNA and maybe spoke to the origin story of the modern city.
Miriam Chotiner-Gardner: I also factored in whether New York had in some way shaped the characters or the story. Not necessarily that the book couldn’t have taken place somewhere else, but the sense that New York played an integral role in exactly how things played out.
Branden Jacobs-Jenkins: I grew up in D.C. and was a bookish kid, so my relationship to New York started through what I was reading, which made it sort of a beacon for me — it felt culturally foundational when people would talk about the myth of New York. I think I chose books that either created that myth for me or seemed to affect the impressions of someone who wasn’t native to that world.
1. “Native Speaker” by Chang-rae Lee, 1995
Henry Park, the narrator of Chang-rae Lee’s first novel, is, in no order: the only son of Korean immigrants, an estranged husband, the father of a dead boy and a seasoned spy. What relationship these elements of his life bear to one another becomes an object of introspection when he is assigned to surveil John Kwang, a city councilman from Queens with mayoral ambitions. Kwang appeals to many of the borough’s working-class immigrants and to Henry, who sees in him “an outlying version” of himself and a point of comparison for his late father. Unspooling his fascination with the politician produces a hypnotically discursive exploration of assimilation’s toll and its characterological tendencies — namely, a knack for compartmentalization and code switching. These qualities, of course, also make for an excellent spy. (To go undercover, says Henry, one must possess “an understanding of one’s self-control and self-proportion: you must know your effective size in a given situation, the tenor at which you might best speak.”) Though the book’s ending suggests they also provide little protection from hate. — Rose Courteau
Katie Kitamura: I was particularly interested in books that revealed structures of the city, and the way they organize experience. “Native Speaker” (1995) really emphasizes how New York is a city of languages and how much language has to do with access to power and recognition. It was the first book I put on my list because I’d happened to have lunch with some novelist friends. It came up and they all said, “If we had written that book, we could just retire.” It’s such an uneasy book, too. Immigration stories can sometimes seem like narratives about hope or finding opportunity. This is a first-generation story that is deeply about displacement, anxiety and trauma.
Jacobs-Jenkins: I think Chang-rae’s superunderrated, honestly. A lot of the things he was doing in these early books other people are only now starting to do. He was talking through ideas of whiteness at a time when no one had the language. He’s my former teacher, so I may be a little biased, but I think this is the first book I read where there was a staging of intersections of immigrant communities — of first and second generations — done in a way that felt unapologetic. And then there’s almost a thriller plot inside of that, which felt very assured and bold and refreshing — there’s no spectacle to it, oddly. This and his novel “A Gesture Life” (1999) are both books I think about a lot.
Michael Cunningham: I agree that Chang-rae Lee should be more famous.
Kitamura: But he is very famous, right?
Cunningham: I know, I know. But there should be more statues. There should be more pop-up shops that sell only Chang-rae Lee-related merchandise. As with many of the others I sought out, this book portrays various New Yorks. One of the things I love about living in the city is that you can’t really go out and walk for 10 minutes and look at the people you are passing on the street and imagine that you are, in any way, a typical member of the human species. That may be at least as true of New York as it is of any other major city, and possibly more so.
Guadagnino: That leads me to my next question, and I’d be especially curious to hear what the fiction writers in the group think about this: Does New York particularly lend itself to fiction?
Kitamura: I will say that stories can sometimes feel bigger in New York. I don’t mean just in terms of fiction but, when I’m in the city, the stories, the dramas, the emotions all seem higher, and I think that lends itself to a certain kind of fiction. But Michael, you should answer — I’ve never written anything set in New York.
Cunningham: And I seem only to write things that are set in New York, primarily because I have lived here for a long time and feel that I can at least speak with a certain degree of authenticity about it. If I lived in Paris, the novels would be set in Paris. Though I suspect it’s more possible for someone like me to live in a Paris in which you’d see very few people who aren’t like you.
Chotiner-Gardner: Michael, can I push back against that a little bit? I agree with that premise by and large. I do think many New Yorkers live in enclaves, though. If you lived in the West Village, where the bookshop I work at is, and never left, I think you’d see a very small stratum of New York. Even though most of us wander the city or try to take in different boroughs or even just ride the subway, some people seem to never do those things.
Cunningham: I totally get it. There’s no denying that there are parts of New York that are sequestered. But I’ll push back on the pushback because I’m speaking to you from the West Village, a block and a half from Washington Square Park. Spend the proverbial 10 minutes in the park and you’ll see a lot of people who aren’t white, boho denizens of the Village. It’s almost a question of which block we’re talking about.
Chotiner-Gardner: Sure, and how much you want to look outside yourself, right? How much you notice and put yourself into other people’s experiences, which is why, to some extent, I think we all come to books.
Kitamura: That’s also a great premise for character building, isn’t it? What they see and don’t see as they move through the city. One thing I think the novel [as a form] does particularly well is capture a relationship between an individual and a larger social context or structure. And I think New York is full of that. You can have singular stories that either engage or don’t with the city around them.
Harris: One thing, though, is that when I was reading, I gravitated more toward novels that presented various enclaves or even characters with slightly blinkered versions of New York. I felt like I trusted that more than I trusted a novel that tried to throw its arms around the whole city and make some overweening statement about it. To me, that’s sort of impossible and, with a couple of exceptions, I don’t really buy New York statement novels. In my experience, you do have these cross-sections of humanity, but you also have a lot of siloed neighborhoods and people who live in a specific version of New York and have managed to make it their own small town.
Guadagnino: Branden, what about you? I know drama is different, but has the idea of setting any of your work in the city felt intimidating or inevitable? Do you think of it as just another place or as something more?
Jacobs-Jenkins: I think every writer has a place in them that, when they think about setting, is actually the font but, with maybe one exception, it hasn’t ever really been New York for me because New York was always where I was trying to get to. I have a greater sense of New York as a literary object that casts a long shadow and as a place of ambition. There’s a Sondheim song from “Company” (1970) called “Another Hundred People” that talks about how the city is built on a constant influx of youth, and who stays and who doesn’t. The idea that if you can make it here, you can make it anywhere was something I felt palpably in my 20s. I’ve spent time away, too, but my husband and I are now returning to New York for the second time; we’re in a different neighborhood, and it feels like we have to reset our entire relationship with the city. It’s a place that’s hard to think of as home, and even then it’s always a new home when you come back to it.
Harris: I grew up in New York City and then, after college, I moved back here with a roommate at the beginning of the crack epidemic. We lived our little life in our apartment and then, after nine months, he said, “I have to get out of here.” He was from Florida originally. He said, “Every time I walk outside, I feel like there’s a knife at my back.” And I was so embarrassed because I thought that was … kind of normal and just the condition of living here. In fact, a lot of the books I picked have some mood of anxiety or dread or terror that connects to how I felt growing up in New York.
Guadagnino: Were you one of the people who voted for “Rosemary’s Baby” (1967)?
2. “Rosemary’s Baby” by Ira Levin, 1967
Those who have seen Roman Polanski’s 1968 film adaptation of “Rosemary’s Baby” will be familiar with the book’s plot: A newly married couple, Rosemary and Guy Woodhouse, move into the Bramford, a storied Manhattan apartment building with a dark past. Soon after, Guy, a struggling actor, lands a plum role on Broadway, while Rosemary, who has become pregnant, begins to suspect their good fortune is the result of their nosy neighbors’ satanic foul play. Ira Levin’s descriptions of the Woodhouse’s new home are as clear as a set designer’s, and he deploys the exhausting, occasionally exhilarating ordeal that is New York apartment hunting to quickly establish the couple’s dynamic: Where Guy is smooth-talking, Rosemary is both dreamy and quietly determined — a combination of traits that make her more than a mere damsel in distress. Subtracting the story’s occultism, what remains is an elegantly simple arc of pregnancy and postpartum distress as a woman realizes that her husband is vain and duplicitous and her doctor indifferent to her complaints, so that finally “she stopped reacting, stopped mentioning pain … stopped referring to pain even in her thoughts.” — R.C.
Kitamura: I thought of “Rosemary’s Baby,” as well. It captures something real about the experience of living in the city.
Harris: I was looking for something scary and I was looking for something about real estate, which is basically the same thing.
Jacobs-Jenkins: I put it out there because it feels like the most interesting novel about theater people to me.
Cunningham: At some point during the conversation, I will feel the need to talk about selection envy. How did I fail to nominate that one?
3. “Another Country” by James Baldwin, 1962
Set primarily in the bohemian New York of the 1950s, James Baldwin’s third novel — published eight years after Brown v. Board of Education, and six before the assassination of Martin Luther King Jr. — documents the grieving friends, family and acquaintances of a Black jazz musician named Rufus, who commits suicide following an affair with a white Southern woman. The country referenced in its title is by turns a literal place — namely America or France, where Baldwin himself famously made a second home — and a metaphorical one, representing the space of human experience and the unformed possibilities that lie beyond American repression. Within this matrix, New York is a city where sex and race are organizing principles: While Black Harlem is where white men purchase sex, the West Village is where they find sanction for gay romance. (“Everybody’s on the A train,” the sexually fluid Rufus tells Vivaldo, an Italian Irish friend who later takes up with Rufus’s sister, Ida. “You take it uptown and I take it downtown.”) Baldwin writes his characters’ many erotic scenes with gravitas, but it’s their conversations that feel most naked and, at times, aspirational for the way they unfold — often full of frustration and anger, but also candid and sustained. Still, he leaves the fate of three of the story’s relationships ambiguous. “Imagine,” Ida says toward the book’s end, that you met the perfect person but “no matter when he arrived would have been too late — because too much had happened by the time you were born, let alone by the time you met each other.” — R.C.
Guadagnino: There were three books with three votes. One was “Rosemary’s Baby.” The second was “Another Country” (1962) by James Baldwin, who made the long list twice, which seems fitting since so many people are revisiting his work as of late.
Kitamura: One thing I was thinking about is how this is a list of the 25 most significant books to us at this particular moment in 2022, so you get a history of New York through these titles, but you also get a portrait of New York and our concerns right now.
Jacobs-Jenkins: I was torn between this and “Go Tell It on the Mountain” (1953), but “Another Country” was appealing because it was a queer touchstone for me and a rite of passage for all the literary 20-somethings I knew in New York who identified as queer. There’s also this obsessive desire to articulate the psychological entanglements of racial and sexual grievance in it. It’s a flawed book in some ways, but it’s also a social novel that captures a very romanticized period, almost in a Henry Jamesian way, in Greenwich Village. I think it was No. 1 on my list.
Harris: Mine, too, I think. It’s the New York novel that made the deepest impression on me, and it fits all our definitions of a New York novel. It’s about a specific circle of friends and acquaintances, but it also takes a big vision of the city. It does this formally shocking thing, too, which is kill someone you are pretty sure is going to be the main character after about 80 pages and then have that death reverberate for the hundreds of pages to come. In some ways, finding out that a person you sort of know dies and then going out for coffee with your friends to talk about it is the most New York story of all time. And then you let that person go and move on to your own obsessions and issues.
4. “Desperate Characters” by Paula Fox, 1970
The neighborhoods may change, but “Desperate Characters” (1970) suggests that the angst of gentrification remains remarkably consistent. Set against the backdrop of the Vietnam War over a handful of days in the late, souring 1960s, the novel follows Sophie and Otto Bentwood, a white couple living on the outskirts of Brooklyn Heights, as they struggle to calibrate exactly how responsible they should feel for the misfortunes of others — most immediately their less affluent neighbors, who are being steadily displaced by newcomers like themselves. The story’s catalyst, however, is not a human but a stray cat Sophie has been feeding that, on the day the novel begins, rears up and bites her, lending a brief sense of urgency to her “edgeless and spongy” existence. While the metaphor of social discord as a festering, potentially rabid wound might sound a bit easy, Paula Fox’s narrative feels singular, particularly in the way it captures, through effervescently intelligent dialogue, the tenuousness of intimate relationships. How, the author asks, does our idea of the public good reflect — or influence — our personal sensibilities? The book, trading in irony rather than righteousness, gives no pretense of an answer. When a character tells Sophie she is “drearily enslaved by introspection,” one might read the accusation as an acknowledgment of the novel’s own limitations. — R.C.
Guadagnino: OK, now we’re going to Brooklyn with “Desperate Characters.”
Jacobs-Jenkins: I think Paula Fox is great, and I wanted Brooklyn representation. This is just the borough I’ve lived in the most, and she feels like the borough laureate of that period. She has a lot of interesting books, but this is the one everyone probably knows the best and that captures that Boerum Hill moment maybe the cleanest, at least until Jonathan Lethem comes along.
Harris: Also, I think there’s a version of New York where people almost never leave their apartments and aren’t that interested in the city, and she’s on that list for me. There’s something hermetic about her work that feels true to New York.
5. “The Fortress of Solitude” by Jonathan Lethem, 2003
Dylan Ebdus, the only white boy on his block in Gowanus, and recent transplant Mingus Rude bond over their ambivalent relationships with their parents and a shared love of comics, bucking the neighborhood’s unspoken rules of engagement. The first half of the book records their fast friendship, written with the bubbly charm of a soda-fueled youth. But clouds loom on the horizon. Even when Dylan and Mingus discover a magic ring that they believe allows them to fly, they cannot alter the veering paths their lives take. Dylan goes off to Stuyvesant High School and then to college in Vermont, while Mingus gets caught up in a scheme to sell drugs and ultimately goes to prison for a tragic shooting. Dylan narrates much of the second half of the book, the section devoted to adulthood. It’s a bold ploy by Jonathan Lethem, and a polarizing one. Prematurely jaded by life and full of shame for having abandoned Mingus, Dylan’s not nearly as fun at 35, but the letdown is intentional. When he returns to his old and now rapidly gentrifying neighborhood, he hardly recognizes the place, just as he can’t seem to make sense of his role in the world. He visits Mingus in prison and tries to give him the ring, which once upon a time let them soar. Now it simply confers invisibility, something that Mingus, who rejects Dylan’s offer, knows all too well. Lethem had written about his hometown borough before — “Motherless Brooklyn” (1999) preceded this novel — but never with quite so much candor, flair or heart. — Miguel Morales
Harris: Regarding Lethem, Branden and I both picked “The Fortress of Solitude” (2003). I love that novel, and I love the musical it became. And then he also picked “Chronic City” (2009).
Jacobs-Jenkins: I could go either way: Whereas “Chronic City” is a weirder book that’s actually about New York, “The Fortress of Solitude” is a love letter to a kind of Brooklyn novel. I find it very moving, and I’ve come across people who claim to appear as fictionalized versions of themselves in it, so it feels like there’s roman à clef energy happening within that social pocket he’s writing about.
6. “Invisible Man” by Ralph Ellison, 1952
It is not an exaggeration to say that this debut novel altered the course of American literature — in part because Ralph Ellison rejected outright social realism, instead embracing a blend of styles and registers that include the picaresque, the grotesque and the dreamlike. “The aim is a realism dilated to deal with the almost surreal state of our everyday American life,” he wrote in response to readers of an early excerpt from the book. “Invisible Man” (1952) tracks the pilgrimage an unnamed narrator — a Black American — takes across the country’s racist underbelly. He begins in the Deep South, with all its attendant humiliations, then joins the Great Migration by moving to Harlem, where he comes across an old couple getting evicted and argues with the authorities on their behalf. His gift for oration makes him useful to the Brotherhood (a stand-in for the Communist Party, with which Ellison grew disenchanted during World War II), but just as the narrator’s profile begins to rise, making it harder for the Brotherhood to order him around, he’s pushed aside. Soon after, he sees an old friend, Brother Clifton, get shot and killed for having the nerve to assert his humanity to a police officer. When the unrest comes, as it must, chaos fully ignites the streets of Harlem. The narrator manages to escape underground, safe but unseen, “outside of history.” Roughly two years after “Invisible Man” was published, Ellison began his hotly anticipated follow-up, a novel he’d never complete. But one book was all it took to show that a story didn’t need to be only a protest, a paean to Black lives or a madcap experiment with form — it could be all of these and more. — M.M.
Guadagnino: I reread “Invisible Man” last year and was struck by how scarily familiar the world it portrayed felt. The writing, by contrast, seemed contemporary in an impressive way.
Kitamura: New York is 100 percent integral to the book, so it’s a great New York novel, but it’s also just a great American novel. For me, calling it “a great New York novel” seems to diminish what the book does.
Jacobs-Jenkins: I resisted including it for the reason Katie mentions, that to say this is a New York novel somehow misses why the book is good. If someone asked me for a New York novel, I wouldn’t hand them “Invisible Man.” I don’t think it would even help them understand Harlem and the politics of the time. The passages that really get me are when he leaves for college — that kind of odyssey feeling. That said, I’m not going to stand in the way of Ralph Ellison’s inclusion.
Kitamura: We do tend to think of the New York novel as operating in isolation, but in New York, everybody comes from somewhere else, kind of, and the idea that those histories and the national history are also baked into the city is something that doesn’t always come through.
Cunningham: I was struck, as I went through the long list, by how often New York is a destination and how many of the books New York could claim are actually about getting to New York or leaving New York. It’s like some kind of “Blade Runner” Oz. Dorothy and her crew don’t want to live in Oz. It’s about getting to Oz so they can get home again. I lost count of the number of novels where people eventually move to someplace like California.
Kitamura: Who among us hasn’t wondered about that?
Cunningham: Yeah. New York as a fantasy — as a place where things will be more interesting or better in some way, as opposed to New York as a place where your family has been for generations.
Chotiner-Gardner: And New York as a proving ground, as a place you define yourself against or in relation to and then either move on from and take what you learned there elsewhere or feel ground down by or whatever. It’s a place you come to and a place you leave, versus a place you stay and inhabit and spend a life in.
Harris: One of the novels I read when I was looking for books for this list is by Betty Smith, the woman who wrote “A Tree Grows in Brooklyn” (1943), called “Tomorrow Will Be Better” (1948). I didn’t like it enough to include it, but it’s definitely one of the best New York novel titles ever.
Chotiner-Gardner: Did many of you read new novels in an attempt to prepare for this? I almost exclusively pulled on what I already had read and knew but, Mark, I appreciate that you went out and did new work here.
Harris: Mostly it was what I knew, but I read a couple out of shame. I tried to do some catch-up work because I knew I’d be with actual literary people. I hadn’t read “Manhattan Transfer” (1925). That was my big discovery as a result of the long list.
7. “Manhattan Transfer” by John Dos Passos, 1925
Following the success of his second novel, “Three Soldiers” (1921), a hard-bitten work of realism partly inspired by his experiences as an ambulance driver in World War I, John Dos Passos seemingly became disenchanted with the constraints of traditional narrative. Any book aiming to portray the teeming masses of New York City in all their muck and glory needed, he must have reasoned, to boldly break with tried-and-true storytelling. As such, his fourth novel forgoes conventional plot structure, pacing and characterization, instead dipping in and out of the lives of dozens of the city’s locals: immigrants, day laborers, newly minted millionaires; a killer, a dishwasher, an actress. Their lives are entwined with the fortunes and pitfalls of the metropolis and — given bits and pieces of their encounters — readers play the role of straphangers, overhearing other people’s intimacies as they course through the city. Tracking how much the city changed from the end of the Gilded Age to the Roaring Twenties, Dos Passos reveals the grubby underside of industrialization. One moment a seamstress daydreams, the next the tulle she’s sewing catches fire, and her with it. “Manhattan Transfer” paved the way for scores of other gritty New York novels, but its blend of the poetic and the profane, not all of which has aged well, remains a product of its time. — M.M.
Kitamura: Did you like it?
Harris: Yeah, although it’s the kind of New York novel I generally don’t like: This big yelling guy who decided, “I can write in the voice of an Irishman. And I can write in the voice of …” It contains all these dialects and accents, and every single one of them is terrible. It reeks of “I can own this entire city through my prose.” And yet I ended up being moved by Dos Passos’s desire to get at all of New York — there’s even gay stuff in it, and it’s from 1925. Even though it would be canceled in nine different ways today. It would be a “Murder on the Orient Express” (1934) situation. Who killed it? Everybody.
Kitamura: I haven’t read it in a very long time. We haven’t got that much from the 1920s and ’30s, so partially I picked it for that reason. I do think it has a lot of problems, but it feels to me like a novel that’s been very influential. You can see shades of it even in something like “American Psycho” (1991) and Don DeLillo. In that sense, it’s been significant. And being significant isn’t the same as being the best, is it?
8. “Passing” by Nella Larsen, 1929
To what extent is race in America, particularly Blackness, a choice, and to what extent is it an inheritance? What are its various obligations, privileges and betrayals? “Passing” (1929), a classic of the Harlem Renaissance, ripples with the complexity of such questions. Set mostly in 1920s Manhattan, the novella follows Irene Redfield, a light-skinned Black society wife, as she reconnects with Clare Kendry, an acquaintance from childhood who has embraced her “white-passing” features, severing nearly all ties to her past and taking a wealthy white husband. Their friendship, at first halting, elicits in Irene an overwhelming gamut of emotions: rage, jealousy and, the critic Salamishah Tillet has argued, sublimated desire. At one point, the book alludes to Rhinelander v. Rhinelander, the 1925 divorce trial in which a white man accused his wife of obscuring her mixed-race ancestry. Though that grotesque case provided a historical precedent for the plot of “Passing,” Nella Larsen’s story stands on its own as an unsettling portrait of two women trying to disentangle the sources of their entrapment. — R.C.
Harris: I thought there would be more ’20s novels, actually. That was one thing I liked about “Passing,” other than the fact that I really loved it.
9. “The Street” by Ann Petry, 1946
More than 70 years after it became an instant publishing sensation and the first novel by a Black woman to sell more than a million copies, this page-turner is rightfully receiving a new wave of attention. Lutie Johnson, a single mother hellbent on providing a better life for her 8-year-old son, moves into a tiny Harlem apartment on 116th Street, a temporary arrangement that gets her “just one step farther up on the ladder of success,” though she’s hemmed in by a handsy super, a neighbor who’s a madam, a son who unwittingly runs afoul of the law and, of course, various power structures. The story illuminates how, absent better alternatives, those down on their luck can fall into vice and violence, but there’s nothing preachy about it. Each character is sharply drawn and, even when acting badly, aches with humanity. Lutie’s aforementioned neighbor Mrs. Hedges, for instance, a busybody, a shrewd entrepreneur and a one-woman neighborhood watch — essentially the block’s Madame Defarge — saves her from getting assaulted, even though she wants nothing more than to pimp Lutie out to their white landlord. Despite every setback, racist put-down and disgusting come-on, Lutie never wavers in her quest, but such faith in the American dream leads to disaster:As Ann Petry writes, Lutie’s son “didn’t have the ghost of a chance on that street. The best you could give him wasn’t good enough.” — M.M.
Jacobs-Jenkins: What’s interesting is how represented Harlem is in the literary world. Not to be this person, but I sort of lumped all these Harlem novels together in my brain and tried to think about which were essential. I just watched the “Passing” movie (2021), but my heart went straight to Ann Petry. I felt challenged by the picture of Harlem she painted, and there’s something remarkable about “The Street” (1946) being a novel from the ’40s that’s almost like a Black feminist text.
Harris: I wasn’t thinking of “Passing” as a Harlem novel, although obviously it is, so much as of how explicitly it’s about different New Yorks and how being able to move unrestricted from one to the other is a privilege and can pose huge dangers and challenges. It’s about that risky shuttling, an essentially New York thing. As for “The Street,” that book has a great sense of the city’s geography. Almost more than in any other novel on this list, you can really feel the streets, how long it takes to walk somewhere, how long it takes to ride the subway there, what it means to drive out of New York and back into it, what it means to round the corner and suddenly feel like you’re on a better block.
Kitamura: It’s a great novel about public transportation.
Chotiner-Gardner: We need one of those on the list.
10. “The Amazing Adventures of Kavalier & Clay” by Michael Chabon, 2000
Michael Chabon took the golden age of comic books, beginning in 1939, as the backdrop for his exuberant third novel, which consists of a delightful series of improbable escapes. For one, the 19-year-old Josef Kavalier flees the Czech capital six months into the Nazi occupation of the city by stowing away in a coffin carrying the Golem of Prague — a legendary protector of the Jewish people, said to have been molded from clay in the 16th century and to have come to life in times of crisis —to safety and takes refuge with his cousin Sam’s family in Brooklyn. With Hitler marching on Europe, Joe and Sam channel their anger, fear and helplessness into developing the comic book superhero the Escapist. Soon, though, they realize a hard truth about the creative life: Their work lacks the power to change the course of current events. When the ship carrying Joe’s brother to America is sunk by a German U-boat days before the attack on Pearl Harbor, Joe enlists to seek revenge and later goes into hiding. Sam, for his part, has fallen for the handsome Tracy Bacon, the radio voice of the Escapist, at a time when gay men are routinely rounded up and thrown in jail. Eventually, the cousins reunite at the top of the Empire State Building and begin the work of revealing their secret selves to their loved ones. — M.M.
Guadagnino: A friend of mine reread “The Amazing Adventures of Kavalier & Clay” (2000) recently and said that, for him, something was lost now that comics have practically taken over all of culture.
Harris: I was a comic book kid, so I loved it on that level. But also, when we started this, I thought I would find more Jewish novels than I did and that there’d be more instances of those midcentury guys who used to battle it out in Esquire taking big swings at New York, but then you think about it and John Updike was actually in Pennsylvania and Philip Roth was in New Jersey. John Cheever took the train in, but his work was mostly about those bedroom communities. And Saul Bellow was in Chicago. It’s surprising that Chabon’s novel, which to me captures that essence and is maybe my favorite Jewish novel, didn’t come until 30 or 40 years after them.
11. “The Golden Spur” by Dawn Powell, 1962
“The Golden Spur” (1962), Dawn Powell’s last published novel, was one of several by the writer reissued in the 1990s after a handful of admirers, including Gore Vidal, championed her work’s resurrection. The book’s premise is simple: A young man, Jonathan Jaimison, moves from Ohio to New York City in the 1950s to find his father, aided only by the cryptic diary entries of his deceased mother, Connie, who spent a brief but, it would seem, romantically prolific time in the city some 26 years earlier. Retracing Connie’s steps leads Jonathan to several of her old acquaintances and to her former haunt, a bar called the Golden Spur, once popular among a downtown literary set and now filled with artists and their groupies. Powell manages to give each character an arc, creating a picaresque, occasionally suggestive novel that satirizes the very concept of a social or professional scene and, more subtly, underscores the stealth women have often needed if they want to have a little fun. Undergirding its humor is sympathy for those trying to find a sense of relevance in a city where it’s easy, as one character fears, to feel “as if all this were building up to the real opera, in which there was no part for her.” — R.C.
Cunningham: One of the books I was wondering why I didn’t nominate was “Breakfast at Tiffany’s” (1958). Is that of interest to anyone?
Harris: It’s definitely significant, but it’s so nasty and sour. I much prefer “The Golden Spur,” where you also have that vibe of going from party to party in 1950s New York. That feeling of the city as this endless, slightly alien social world of house parties, which I love. “Breakfast at Tiffany’s” is probably my least favorite of that category.
12. “Open City” by Teju Cole, 2011
The ubiquitous figure of the flâneur — a passive, strolling observer of urbanity — finds renewed depth in “Open City” (2011), whose narrator, Julius, a psychiatry fellow living in Morningside Heights, wanders New York as a form of therapy. What he describes while walking is often not what he sees but what has disappeared. Looking out on the construction site where the twin towers once stood, he contemplates the many communities that dwelled there previously, deeming the area “a palimpsest, as was all the city, written, erased, rewritten.” Landmarks, too, he examines for what they fail to represent: Ellis Island, “the focus of so many myths,” he points out, can hardly speak to the memory, or offspring, of Africans imported to America’s shores as captives. This last point is of personal import to Julius, who emigrated from Nigeria and finds himself the object alternately of white characters’ racism and Black characters’ presumptions of brotherhood. (“I’m African just like you,” chides a cabdriver when Julius fails to greet him.) Cerebral and capacious, Teju Cole’s novel asks what it means to roam freely. — R.C.
Kitamura: In thinking about how people move through New York, I was also thinking about “Open City,” in which the protagonist, unlike some of those characters in the ’20s, can just walk everywhere. It makes you think about what kind of city is revealed to us based on where we cannot go, and this idea of public space and how it operates within a New York novel. And there’s a sense of levering open the city from a very contemporary perch to access its history. I felt like that character was a bit of an archaeologist. I do think it’s an influential novel. When I’m teaching, it comes up again and again as something my students would like to be able to do.
Cunningham: Do we want to go back to this question of whether it’s reductive to call certain great novels New York novels? Do certain books not make the list because they’re so much more than New York novels?
Chotiner-Gardner: It’s interesting, I don’t see those as necessarily being in conflict. To me, the New York novel is a subset of the great American novel, and those two things can exist in parallel and actually in conversation.
Guadagnino: Miriam, I’m curious whether, at the store, the New York novel is a real category. Is it something that people often ask for recommendations on?
Chotiner-Gardner: It certainly is. I’d say we get asked for our favorite books about New York a few times a month, mostly by tourists who want to go home with a quintessential New York book. We have rotating staff-favorite tables around certain themes, and we’ve integrated books about New York into that. They always sell incredibly well, and I think that’s when some New Yorkers come to them, when you call them out.
Jacobs-Jenkins: Now, we’re a group of writers whose conversation is devolving into semantics, but I want to tap into something Katie said about the idea of significance. It’s worth thinking about what that means for some of these. In some ways, “Open City” doesn’t exist without “Invisible Man,” so does that mean I should defer to “Invisible Man” as the forefather of that? I think I’m also having a reaction to all of these stories of Black lives set in Harlem, which feel like a disservice to the city itself. I’m wanting to expand the representation of diaspora life in New York, and now I’m suddenly like, “Where’s Jacqueline Woodson? Where’s Paule Marshall?” Marshall’s “Brown Girl, Brownstones” (1959) is about a Barbadian family living in Brooklyn. I would say it’s a very good book.
13. “Brown Girl, Brownstones” by Paule Marshall, 1959
By the time Paule Marshall decided to channel her childhood into her first novel, the white literary establishment had developed certain tastes for fiction by Black women: These books should be set in Harlem, concerned with the lives of African Americans and plugged into the issues of the day: poverty, crime and so forth. But much like Selina Boyce, the book’s heroine, “Brown Girl, Brownstones” defies expectations. The action takes place in Brooklyn’s Bedford-Stuyvesant neighborhood, the Boyces are Barbadian immigrants and, like many other West Indies expatriates, they are upwardly mobile, stretching for that final rung on the ladder to middle-class respectability: homeownership. Silla Boyce, the driven matriarch, pours all her resources into this goal. When her husband inherits a plot of land in Barbados, she sees a chance to make a down payment on a brownstone; he sees a fresh start in their homeland. Amid this conflict, Selina, torn between the two possibilities her parents represent — assimilation or repatriation, a choice that reflects both a burden and a birthright — grows older and wiser. Near the end of the novel, once she’s decided for herself what she wants from life, her mother says, “You was always too much woman for me anyway, soul. And my own mother did say two head-bulls can’t reign in a flock.” While clearly hurt, Silla cannot hide her pride for her daughter, now a woman with a will of her own. — M.M.
14. “Bright Lights, Big City” by Jay McInerney, 1984
Some novels chart their characters’ descent into debauchery; others make it their starting premise. “Bright Lights, Big City” (1984) belongs, thrillingly, to the second category, opening on its young unnamed narrator at a Manhattan nightclub as he searches for yet another line of cocaine — “Bolivian Marching Powder,” he calls it — knowing all the while that he has nothing left to extract from the night but “gratuitous damage and the palsy of unraveled nerve endings.” Such funny, often incisive self-awareness doesn’t save the narrator — a fact checker at a magazine that sounds an awful lot like The New Yorker — from an accrual of bad decisions, but it does propel the story forward with the speed of a stimulant. Told in the rare second person and published during Ronald Reagan’s first presidential term, Jay McInerney’s touchstone novel immortalized the louche glamour to which a certain 1980s New York set — the sort of people who might, for example, opine with a sense of authority on the quality of a revamped Vanity Fair — aspired. (“It’s the Abstract Expressionist approach to publishing,” says an ad man. “Throw ink at paper. Hope for a pattern to emerge.”) But much like the era’s most iconic New York institutions (the Odeon, Raoul’s), a number of which it features, the book remains substantially appealing — not just for its vibrancy but for its ultimate tenderness, which feels, weirdly, like wisdom. — R.C.
Harris: There’s also interesting, debatable New York cocaine/downtown ’80s stuff that we have to choose from.
Jacobs-Jenkins: That’s really one of those cornerstones. It’s either ’80s coke books or Harlem in the ’20s.
Harris: We could make the case for “Bright Lights, Big City.” It does a pretty great job of conveying: “I’ve come to New York. I want this to be the city of my dreams. I want to make it here. And I’m about to crash into a set of really ugly realities.”
Jacobs-Jenkins: I would co-sign on “Bright Lights.” As someone who worked at a magazine, I think of it as one of those beaconlike culture books that everyone in publishing has probably read at some point. And it’s the most successful second-person book I can think of, honestly. It’s really fun.
15. “Speedboat” by Renata Adler, 1976
“There doesn’t seem to be a spirit of the times,” says Jen Fain, the book’s narrator, about the 1970s. Indeed, a deep respect for incoherence animates “Speedboat” (1976), which eschews a conventional plot in favor of nonchronological and episodic storytelling. Jen’s job as a reporter for The Standard Evening Sun,a fictional New York tabloid, lends itself to this approach, with the character mingling observations from her own life with those of friends and strangers. Some are funny. (On the paper’s obituary writer: “He gets things wrong, but he gets them in detail.”) Some, ruthlessly honest. (She admits, among other things, to “racism and prudishness … and reading over people’s shoulders.”) Others are provocatively aphoristic. (“‘All acts are acts of aggression …,’ the professor said. ‘The point is to give them other properties.’”) Many are no longer than a page. Taken together, these perspective-shifting passages recreate the cacophony not just of New York City but of modern life more generally, by the ever-growing glut of information and secondhand experience the average person must metabolize. Renata Adler’s fragmented narrative demonstrates that a sustained attempt to do so democratically can be both pleasurable and perilous. “The point changes and goes out,” Jen says. “You cannot be forever watching for the point, or you lose the simplest thing: being a major character in your own life.” — R.C.
Jacobs-Jenkins: I put this down because I wanted a counterpoint to “Bright Lights, Big City,” which I figured would wind up on the list. Somehow, it’s the other half’s experience of that speedy part of New York. It’s another one of those books people passed around when I was an editorial assistant, and it felt like a discovery. It’s a delicious read, and not out of place in this moment of autofiction, although this was before we had a word for it. I’m a sucker for these weird, ’70s what-the-heck-is-this kind of books.
Cunningham: It’s also interesting in that it’s based in New York and yet we keep leaving New York, do you know what I mean? Almost all the folks we’re talking about are going toward New York, and this is uniquely about Renata Adler being in New York, going away from it and then always coming back to it, which I love. It felt like a different thing, where the city is the given, and then you travel and find the strangeness elsewhere.
Harris: I kept wanting there to be a Joan Didionesque New York book. It does seem like one of these choices should be fragmentary and jagged and alienated and nervous in the way that “Speedboat” is. It just feels like a great flavor of New York book that we don’t have represented anywhere else.
Chotiner-Gardner: Can I ask one more question about significance? I chose books that were significant to me and that I thought were great fiction. Did anybody pick books they didn’t like but thought were significant?
Harris: I didn’t put things on my list that I didn’t like. I mean, I’m certainly not going to make the case for “Rosemary’s Baby” as a great piece of literature, but I will make the case for it as a great piece of plotting, and I really like it.
Jacobs-Jenkins: I put things I would be excited to see on a list like this, not necessarily that I would die to read again. Part of the prompt was to provoke conversation, and some of mine were about challenging the expectations I imagine the average reader has coming to a list like this. But I still feel like I could defend every choice I made.
Cunningham: I made a couple of nominations I will not be defending.
16. “The Flamethrowers” by Rachel Kushner, 2013
We never learn the name of the young woman who narrates much of Rachel Kushner’s second novel, but we do know she’s from Reno. That becomes her nickname, as well as a piece of conversational armor and a persona to adopt, after she moves to 1970s New York City and falls in with a loose group of downtown artists and those who love them. A novice filmmaker, she belongs uneasily to both categories, having shacked up with Sandro Valera, an older, far more established conceptual artist and reluctant member of the rich and influential Valera family. The relationship is tested when they visit Sandro’s family estate in Italy on the eve of the student movement of 1977. There, Reno sees for herself what sort of people the Valeras are. “I was the one shopping for experience,” she later says of a different disappointment, summing up her tendency to throw herself in harm’s way, though to call “The Flamethrowers” (2013) a coming-of-age novel would be to slight the writing’s range and ambition. Kushner uncorks a tale that spans more than half a century and moves as quickly as Reno rides her motorcycle across the salt flats of Utah, briefly becoming the fastest woman in the world. But experience is costly; she totals her motorcycle on her first attempt, badly injuring herself in the process. Similarly, Sandro partly owes his start as an artist to his family’s riches, built on the backs of indentured servants tapping Brazilian rubber trees. Those tensions, between discovery and destruction, invention and exploitation, power “The Flamethrowers” to its unsettling conclusion. — M.M.
Kitamura: I could get behind “The Flamethrowers.”
Chotiner-Gardner: I love that book. It’s partly set in Italy, of course, but I thought the New York sections depicting the art world in the ’70s were pretty incredible. And just her prose on the page.
Jacobs-Jenkins: I felt similarly. I didn’t include it because of the Italy sections, which to me feel like such a huge part of the drive, but I mean, I’m a geek for that performance-art, downtown-scene-adjacent kind of portrait.
Kitamura: Those sections on the art world are done incredibly well. It’s hard to come up with an inventive fictional body of artwork that actually holds water, and she totally does it.
17. “Jazz” by Toni Morrison, 1992
There was no slowdown for Toni Morrison after the triumph of “Beloved” (1987). Her subsequent book, “Jazz” (1992), takes its cues from just that, riffing on one fateful day in 1926. Joe Trace shoots his lover, Dorcas, an event that would come at the climax of most novels but that Morrison boldly puts at the start of hers. She then revisits the incident and its echoes from multiple perspectives, treating her novel’s characters like players on a stage who are each gearing up for a big solo. It’s a democratic approach to the Jazz Age; you won’t find the Cotton Club, Langston Hughes or other leading lights of the Harlem Renaissance in these pages. Morrison takes an era steeped in nostalgia and makes it new, writing of lives tightly circumscribed by daily routine — “You can’t get off the track a City lays for you” — of regular folk like Trace and his wife, Violet, who arrived in New York so full of hope and promise. Their desires, frustrations and obsessions mirror those of the narrator, who bobs and weaves around the story, passing judgment on Joe’s crime of passion, the tragedy of Dorcas’s curtailed life, the rage that grips Violet and the unlikely path to reconciliation in store for husband and wife. Is this voice, so hungry to discover the forces that bond and split people apart, Morrison herself or some disembodied spirit of the metropolis responding to the want and hurt filling its streets? Whoever it is, it sets the novel’s pace, and Harlem’s music swells when it speaks. — M.M.
Jacobs-Jenkins: I felt compelled to try to get Toni Morrison on the list, and “Jazz” is one of my favorite novels of hers. People seem either to love it or to hate it, but I think it’s such a magical, lyrical portrait of Harlem, written extemporaneously. She really used the scholarship that was amassed about the social world of Harlem retroactively to flesh out the literary imagination of that space. It’s one of the most influential things I’ve ever read, and I’m constantly pushing it on people.
18. “Ragtime” by E. L. Doctorow, 1975
It’s hard to summarize “Ragtime” (1975), which interweaves legendarily real characters (the escape artist Harry Houdini, the anarchist Emma Goldman, the model and chorus girl Evelyn Nesbit, the financier J. P. Morgan) with purely fictional ones (among them a Westchester family that owns a fireworks business, a destitute immigrant peddler and his daughter, a young mother driven to desperation and the Harlem pianist who woos her). It’s more illuminating, perhaps, to consider the musical genre from which the book takes its title: Originated by Black musicians and popular in the first two decades of the 20th century, ragtime used syncopation to create a sense of swinging looseness in its listeners. E. L. Doctorow’s novel, set between 1902 and the twilight of the 1910s, does something similar — emphasizing the mundane next to thesupposedly major, so that a captain of industry becomes a minor character compared to a young boy who understands intuitively that “the forms of life were volatile and that everything in the world could as easily be something else.” Where better to illustrate this point than New York City and its environs, where lives regularly intersect in the most improbable of ways? — R.C.
Jacobs-Jenkins: This was one of my Covid rereads, and it’s an amazing book. It’s one of these weird miracle books from the ’70s that sort of came out of nowhere. I love the way it incorporates real history and gives an interesting social panorama of that era in New York. Granted, a lot of it is set in New Rochelle — the rest of it basically jumps around Manhattan — but I love the idea of a book that doesn’t pretend that everyone w