Be they harsh and harrowing or nostalgic and romantic (and sometimes both), this handful of the classic as well as some more recent works of fiction to come from or be about New York’s most famous borough includes stories most concerned, at their core, with characters poor, unhappy or both.  Interest, unsurprisingly, lies where there is struggle. As Tolstoy said, “Happiness is an allegory, unhappiness a story.”

Betty Smith’s A Tree Grows in Brooklyn (1943)

Like Pearl S. Buck’s classic A Good Earth, A Tree Grows in Brooklyn is one of those timeless works that new generations of readers come to and love. It didn’t do badly in its day either, selling 300,000 copies in its first six weeks. Betty Smith’s beautifully rendered story, rich in the kind of traditional narrative pleasures you would associate with Steinbeck and maybe Dickens, is about an Irish family who have just moved to Williamsburg, Brooklyn at the beginning of the 20^th century. Like so many immigrant stories, it is a story about struggle, about overcoming poverty and about finding your place in a new world. Perhaps this sounds old hat, but there is nothing tired when a story is filled this richly with characters like the wonderful protagonist, Francie, who works so hard to overcome her circumstances, a girl destined to become a writer. What’s so powerful is the degree to which we not only sympathize with Francie’s hard-working mother, who must basically run the household alone, but that we actually don’t hate and are in fact much intrigued, if totally infuriated by, Francie’s drunken but enchanting father, Johnny, the singing waiter who would never become the artist Francie seems destined to become.

Colm Tóibín’s Brooklyn (2009)

Colm Tóibín is not from Brooklyn, he’s never lived in Brooklyn and doesn’t seem to have any plans of moving there, trendy as it has become these last couple decades. That said, Tóibín doesn’t have any plans of being a woman either, despite the fact that he displays a brilliant ability to write from their perspective, as evidenced in Brooklyn.  In other words, as the fiction writer’s job is to imagine, it’s not so farfetched to have an outsider like Tóibín share with us a place as rich as early 20^th century Brooklyn. In the sparsest of prose, Tóibín’s painting of turn-of-the-century Brooklyn is not a clichéd picture of the brownstones and baseball fields readers expect. No, Tóibín is much too smart for that. His Brooklyn is painted with character sketches that ring rich and true. We see the borough not so much in distinct filmic visuals but rather in atmospheric swaths. A place is a feeling as much as a sight and this is the memory of feeling that Tóibín’s masterfully crafted work presents.

Jonathan Lethem’s Motherless Brooklyn (1999)
and The Fortress of Solitude (2003)

Born and raised in Brooklyn Jonathan Lethem clearly follows the old writer’s dictum to ‘write what you know,’ at least when it comes to his books’ settings. After living for a time in San Francisco, Lethem moved back to his hometown in 1996. It was a good move. Three years later he would publish what many consider one of his richest works, Motherless Brooklyn, probably the lightest of the books on this list. Framed as a detective novel, Motherless Brooklyn is a post-modern tale narrated by an unlikely detective who suffers from Tourette’s (the syndrome of tics both physical and verbal) and is obsessed with language—and oh, the word play Lethem will get to engage in with such an unusual narrator. This genre bending—or perhaps, rather, genre combining—novel impressed Time magazine enough to elicit comparisons with a few other legendary genre-blending writers, including Margaret Atwood and Michael Chabon (The Amazing Adventures of Kavalier and Clay). The book won the National Book Critics Circle Award and was named book of the year by Esquire magazine. If that weren’t enough, Edward Norton has apparently spent the last ten plus years trying to bring the novel to the big screen.

The Fortress of Solitude is not only Superman’s hideout, it is the title of what was Lethem’s next novel. Also set in Brooklyn, this far more straightforward bildungsroman tells the semi-autobiographical story of a boy named Dylan. Though not exactly harrowing, there is a darker side to the Brooklyn of the 1970s and 80s presented here as compared with the more romantic, nostalgic images in Smith and Tóibín’s books. The Fortress of Solitude is a tale of racial strain, apt considering the hot bed of tension that Brooklyn was in that era. Music is central to the novel and Dylan’s eclectic taste—from hip hop and R & B to punk and classic rock—tells us much about the mixed world he comes from. But Dylan’s (or Lethem’s) Brooklyn is also a place of drugs, of marijuana in the 60s and 70s and of cocaine after that and the inevitable havoc it wreaks on some of the novel’s characters’ lives. In the book’s first sections though, The Fortress of Solitude is about comic book-loving kids growing up. Indeed, a comic book theme runs throughout the novel, including a magic ring that helps explain the novel’s title. One gets the sense too that after moving from New York as a young adult, Dylan’s eventual return to Brooklyn after he’s grown up (much like Lethem) is like Superman returning to his fortress of solitude—the only place where he can be himself.

Hubert Selby Jr.s Last Exit to Brooklyn (1964)

What began as a short story, entitled “The Queen is Dead,” would become a cult classic that lives on a half century later. In their review of Last Exit to Brooklyn, The New York Times wrote, “To understand Selby’s work is to understand the anguish of America.” This tale takes us deep into the lower classes—the lowest of the low—of Brookyln in the 1950s. What matters most, perhaps, is the novel’s distinctive style, which doesn’t follow the rules of grammar, spelling and punctuation. Selby wanted his narrative to sound like one friend talking to another in a bar; it is, as a host of critics have pointed out, a decidedly unpretentious style. And the style is all the more central for it sets the tone that connects what some consider a collection of stories rather than a novel in the traditional sense. Last Exit to Brooklyn covers all sorts of taboo subjects, with characters as varied as street thugs, prostitutes, a union official and transvestites. To call the novel depressing would not be an exaggeration, and yet the power of its style and the unbridled honesty behind it led beat poet Allen Ginsburg to pronounce on the book’s release that it would “explode like a rusty hellish bombshell over America and still be eagerly read in a hundred years.” Almost halfway there, it seems Ginsburg’s prophesy could well come true.

Paula Fox’s Desperate Characters (1970)

Success is generally made up of some combination of luck and talent. The optimists among us hope that talent ultimately trumps luck. Such is the case with Paula Fox, though the success of Desperate Characters was no straight path. Far from. Fox was clearly a talented writer in 1970, when her second novel came out. She was not, however, so lucky. Despite meeting with fiercely positive reviews, “Desperate Characters” did not sell well. It barely sold at all, eventually going out of print. The story goes, it was Jonathan Franzen (The Corrections, Freedom) who championed the book and got it back in bookstores nearly three decades later. He wrote the preface to the current edition.

Desperate Characters is one of the few novels here not concerned with the lower classes. Written in 1970, it is about that dark and very different Brooklyn so far removed from the arty, yuppie borough we see today. Otto and Sophie, the childless married couple at the centre of this novel, are unhappy, not in love and paranoid. They are paranoid in the literal sense, as Sophie is bitten by a cat early on in the story, and she and Otto worry after that she has gotten rabies. A central plot point of the novel, it sounds downright silly in the retelling—such a small thing as a bite from a cat—and yet Fox’s novel derives nearly all its tension and stress from it. Of course, the true fear at the heart of the novel is a middle-class paranoia of what feels to the couple like the ever encroaching crime and vandalism around them. The world outside feels like anarchy, and this to a couple that is ever on the verge of self-destruction.

Jennifer Egan’s A Visit From the Goon Squad (2010)

Clearly one of the biggest books of last year, Jennifer Egan’s A Visit From the Goon Squad won both the National Book Critics Circle Award and the Pulitzer. Although Egan, who hails from Brooklyn, does not set her best received novel there, her characters certainly have enough suffering to keep good company with many of the other Brooklyn-based books on this list. If this rather self-destructive bunch, many of whom are connected in some way with the music industry, find happiness—and most don’t—it is short lived.

With “The Sopranos” cited by Egan as one of the main inspirations for the novel’s structure (Marcel Proust was the other), it was probably rather exciting, and perhaps not completely surprising, to learn, not two days after being awarded the Pulitzer, that her novel was optioned by HBO. A genuinely inventive novel, some, for lack of a better term, have described it as post-post modern. But this is to do a clearly wonderful book a great disservice—the words ‘post’ and ‘modern,’ when pushed together, are not usually the most effective adjectives for selling novels. Whether seen as a novel or a collection of short stories, each chapter of Egan’s fifth novel, concerned ultimately with the effects of technology on our lives and on our perception of time, is told by a different narrator. To give you a sense of how many characters (13) and how far reaching (it spans 40 years) the novel runs, here is a portion of the plot summary as delivered by Will Blythe, in his NY Times review of the book: “The book starts with Sasha, a kleptomaniac, who works for Bennie, a record executive, who is a protégé of Lou who seduced Jocelyn who was loved by Scotty who played guitar for the Flaming Dildos, a San Francisco punk band for which Bennie once played bass guitar (none too well), before marrying Stephanie who is …” And that’s not half of the half of his summation of the storyline. Not to mention the multiple perspectives from which it’s told. At one point the book veers into the ever dangerous territory of the second person, at another the story is told as a power point presentation, and one that more than a couple prominent reviews referred to as moving. With much humor and clearly a striking ability to tell a tale (or rather 13 tales) in any number of fresh and interesting ways, A Visit From the Goon Squad may not be the quintessential Brooklyn novel (it is set mainly in New York), but it is a great novel that seems deserving of a spot on this list.

Whether it’s the relatively gentle glow of Betty Smith’s nostalgia to the tragic depths of Paula Fox’s doomed couple, be it the street level Selby version or the genre-bending Lethem type, Brooklyn has proved fertile ground for some of the best literature to emerge over the last hundred years.