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What’s the best New York Jewish book of all time?

Literary cities are many, but there’s only one New York.

Now, philanthropists Bradley Tusk and Howard Wolfson are acknowledging that fact with a new award for books set in or about the Big Apple, which will come complete with a $50,000 prize. The news of the Gotham Book Prize arrives at a time when the city is reeling from the effects of the coronavirus pandemic, and is designed to support writers who continue to tell its stories. (We’re told there are eight million of them.)

We’d be remiss if we didn’t take a moment to mention the many brilliant books that should have taken home the prize in the past. If we could wind back the clock and honor the best, here’s what we’d choose.

“Call it Sleep” by Henry Roth (1934)

Before that other Roth from Newark made a splash, Henry Roth was touted as the Jewish James Joyce. Yet this tenement tale of an immigrant family, while heralded as a masterpiece, was a commercial failure on its release. It took 30 years, a second print run and the championing of critics Irving Howe and Leslie Fiedler for the novel to earn its rightful place among the canon. Imagine what a Gotham Book Prize might have done for its reputation.

“Marjorie Morningstar” by Herman Wouk (1955)

The titular Marjorie changes her name from Morgenstern to Morningstar, hoping to become an actress. She meets and falls for an older man, Noel — formerly Saul — at a resort camp. Together they clash over tradition, the pressure of assimilation and the sacrifices one makes for fame. In the end, Marjorie is the more pragmatic, ditching the feckless Noel — and the hope of show business — for the domestic New York life he always said she was fated to. Whether the overall takeaway and tone of Wouk’s writing is proto-feminist, dismissive of ambitious women or merely realistic about the prospects of making it in show business remains open to debate. But Wouk’s sensitivity to his female subject is greater than that of his male contemporaries, and even many of his successors.

“Shadows on the Hudson” by Isaac Bashevis Singer (1957) English translation by Joseph Sherman (1998)

Originally written in Yiddish and serialized in the Forverts, “Shadows on the Hudson” tracks the lives of Jewish refugees on the Upper West Side in the late 1940s. The characters are well-off, an uprooted intelligentsia living comfortable lives. But the novel, with its breezily macabre insights, is haunted by the spectre of the Shoah. At the source of the characters’ grief is not just survivor’s guilt, but the profound sense that European world they left behind can’t be recovered.

“The Best of Everything” by Rona Jaffe (1958)

It’s attractive, in its way, to imagine Nora Ephron or Gloria Steinem emerging out of the second-wave feminist ether without precedent, but in many ways Jaffe established the template for their work. Her best-known novel, set in the world of publishing, follows young women navigating the Manhattan workplace in the “Mad Men” era with all its attendant sexual harassment — “Shitty Men in Media List,” your concerns are eternal. Jaffe’s characters have candid discussions about sex and the continual ways in which men disappoint, abandon or abuse them. In other words, it feels strikingly relevant to contemporary New York.

“Franny and Zooey” by JD Salinger (1961)

Only half of “Franny and Zooey” takes place in the city, and that half takes place entirely within the confines of an apartment. And yet, that’s what makes the novel — more than “Catcher in the Rye” or the New York-set tales from “Nine Stories” — such an irreducibly New York book. In the book’s medicine-cabinet minutiae, Salinger hit at a fact of New York life: New Yorkers would, just as often as not, prefer to stay home and kvetch about our existential angst. Also, the family cat in the story is named Bloomberg. Need I say more?

“The Power Broker” by Robert Caro (1974)

To understand New York, one must first understand Robert Moses. This monumental Pulitzer-winning work explores how Moses, an official for the city who wielded unprecedented control over its urban planning, was fueled by racism, classism and an insatiable thirst for control. If you want to know why highways gird Manhattan: Read this book. Wondering why the city has such an abundance of (tiny) parks: Read this book. If you’ve ever given a thought to urban sprawl or bumper-to-bumper traffic or the lack of infrastructure in poor communities: Read this book. If our president claims to be New York’s master builder, Caro’s book shows us just how much he fails to measure up to Moses’ truly dangerous brilliance.

“The New York Trilogy” by Paul Auster (1985-1986)

This triptych by New York’s foremost pulp revivalist is a dizzying postmodern work blended with hard-boiled detective tropes. Their detective plots are confusing — who’s telling the “Paul Auster the writer” character what to write? — but tap into a vein of loneliness and urban hermitage endemic to the city whose glory days are behind it. New York binds the books and provides the clues to their mysteries.

“The Odd Woman and the City” by Vivian Gornick (2016)

A peripatetic ode to sidewalks and byways, this memoir is as trenchant a piece of writing as one might expect from the inimitable Ms. Gornick. The memoir musters all the jaded, bittersweet, ambivalent and tender nuance a lifelong New Yorker could bestow on her hometown. It’s both a look at the nature of urban relationships and a self-affirmation for a woman whose most enduring companion is the city itself.

“The Amazing Adventures of Kavalier and Clay” by Michael Chabon (2000)

Sammy Clay and Joe Kavalier are cousins and comics industry pioneers whose superhero inventions look almost dull in comparison to their New York odysseys. Among their adventures: The pair gatecrash a party at Salavdore Dali’s home; Sam has a tryst at the World’s Fair grounds; and Joe defies death with a leap from the Empire State Building. Spanning the 1930s to the 1950s, Chabon’s Pulitzer-winner adds an aura of magic to Marvel and DC’s Golden Age, making explicit the link between Jewish culture and the spandex-clad crusaders that dominate our culture.

“Nonstop Metropolis” by Rebecca Solnit and Joshua Jelly-Schapiro (2016)

Jelly-Schapiro and Solnit’s gorgeous atlas of the city is not your typical collection of maps. Their two-page projections plot out not just streets and subway lines, but the broader culture of the city. One map shows the radius of Spanish-language radio transmissions. Another charts the garbage flow out of the city. A calligraphic rendering of Staten Island marks Chinese landmarks and the Liberian-American projects that gave rise to the Wu-Tang Clan. It’s not just the maps, either. The book brims with interviews and historical essays, making“Nonstop Metropolis” an essential guide to understanding New York’s inimitable diversity and endless eccentricities. And, yes, it’s so comprehensive that there’s even a section on New Jersey.

PJ Grisar is the Forward’s culture reporter. He can be reached at [email protected]

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