The Dark Side of Night— A Grim Gotham Nocturne

101005 article book dobr The Dark Side of Night— A Grim Gotham NocturneWhen I picked up Mark Caldwell’s New York Night, I was expecting a romp through Gotham’s fabled wee-hour life—restaurants, cabarets, theaters, jazz clubs, speakeasies, poetry readings. Mr. Caldwell, I thought, would escort me to Mrs. William Backhouse Astor’s famous gilded balls for the Four Hundred, and to the salons and parties that lit up Harlem in its heyday. We’d visit Metropolitan Opera openings, the Stork Club and after-hours dance clubs where illegal drugs flourished. We’d see the night’s high life and low life, early and late.

Alas, no such luck. Mr. Caldwell, a Fordham University professor whose last book was A Short History of Rudeness, takes a grim view of nocturnal New York. Early on, he calls night “a dark mirror that obscured what daytime spotlighted and showed monsters and miracles to which morning and afternoon were blind.” He stays true to that spirit. Instead of getting the view from a limo, the reader rides in a squad car. Along the way, we encounter plenty of vice, murder and macabre goings-on.

But c’mon—isn’t a New York night full of glamour, too? Shouldn’t some nights out in the country’s most sophisticated metropolis be exhilarating?

A cheerfully exuberant New York night sometimes appears in Mr. Caldwell’s book, but not for long. He breezes through those parts, as if he were an unwelcome guest hurrying off to nastier places. For instance, he takes up the birth of the city’s restaurant mania in the late 1950’s with the opening of the Four Seasons and the Forum of the Twelve Caesars—where “the food was dressed up as if for a toga party.” Less than two pages later, however, he writes: “But it was a short walk from the Four Seasons, the new El Morocco, or even the Latin Quarter, to a darker New York.” Then he describes how Billie Holliday died after yet another drug arrest, and how West Side violence thrived despite the building of Lincoln Center and gave rise to the infamous Capeman murder of August 1959.

A year (and a few pages) later, Mr. Caldwell drops in on the midtown cabarets that once helped make Times Square throb. He takes readers into Jack Silverman’s International Theatre Restaurant—but it’s the night that the police busted headliner Sophie Tucker for failing to carry a $2 cabaret license card, closing the place for four nights. With New Yorkers fleeing to the suburbs and 1950’s Modernist office buildings invading midtown, the episode signaled the end of an era.

So if this book isn’t about nightlife in the glittery, conventional sense, if it never ventures into Mrs. Astor’s ballroom, what is it?

Mr. Caldwell starts his history in 1643, with a description of a nighttime massacre of Indians in New Jersey by the Dutch of New Amsterdam, followed by “aftershocks” that kept coming in which “drink was the usual trigger,” and “most readily at night.”

That last phrase suggests the epic territory Mr. Caldwell claims, and then stretches. Admitting that night did not begin a life of its own until the 18th century, he wanders from the start and never stops. He describes black funerals in the 18th century and boarding-house life in the 19th. He justifies a digression on the dreadful Tombs prison, circa 1870, with the phrase, “the Tombs was particularly terrible at night.” He riffs on the Beats and Joe Gould and the novels of that era. He details a 1948 heat wave, then somehow segues into discussion of a perceived rise in the illegal drug trade.

In one curious (and lengthy) passage, Mr. Caldwell chronicles the death of Madame Restell, “the highest-profile abortionist in New York and indeed the country,” who took her own life one, well, morning.

Indeed, Mr. Caldwell takes so many detours and strays into so many cul-de-sacs that readers may be forgiven for wondering if they’ll ever make it to the final destination, whatever that’s supposed to be. Once, describing the life and citing the diary of one William Dunlap, who lived in Greenwich Village in the 1830’s, Mr. Caldwell even admits that his stretch is acrobatic: “He almost never records anything of interest happening after dark,” Mr. Caldwell confesses—Dunlap was a temperance advocate who avoided the nocturnal drinking rounds.

If Mr. Caldwell were a less talented writer, his readers might be tempted to blow out the candle. But he can be a vivid storyteller, scene-setter and phrasemaker. When Trinity Church caught fire, “flames pounded the sanctuary and nave, then slapped at the tower, roaring up to the wooden pinnacle.” When its el came down in 1955, “Third Avenue emerged from beneath its tracks and girders like a hungover drunk waking up in the sunlight.” When high and low were about to clash at the Astor Place Opera House in 1849, “opera was ambrosia to a self-professed elite but chloroform to the masses.”

Mr. Caldwell’s broad sweep is welcome when he writes about the gaslights, the buses and subways, and the other new technologies that gave life to the night. There’s a wonderful passage when he quotes a writer visiting a brothel. There, the john discovered a new pleasure—pure running water coming from the new aqueduct system. The happy, clean customer wrote: “we cannot reveal to vulgar gaze the rapture that ensued.”

But Mark Caldwell never forsakes his dark focus. At the very end, he visits Flash Dancers, a Broadway strip joint in midtown. Despite the loud music and the flashing lights, the patrons are immobile; “the most surprising thing about it is its gravity,” he writes. Exactly like his book.

Judith H. Dobrzynski, former executive editor at CNBC and former New York Times reporter, is a writer in Manhattan.