FROM ITS EARLIEST DAYS, Times Square floated on a mighty ocean of alcohol—nickel beer, gin, whiskey, wine, and the fine champagne downed by the quart at Rector’s and Shanley’s. The artistic souls who passed their days and nights along Broadway—the actors and the hoofers and the chorus girls and the composers and writers and stage managers and agents and producers and ticket scalpers—soothed their frayed nerves and bucked up their faltering egos with nightly drafts from the local dives and taverns, the lobster palaces and the hotels. In Mirrors of New York, a thoroughly soused memoir dating from 1925, the essayist Benjamin de Casseres describes Times Square as the central depot of a “Grand Trunk Line of Booze” stretching down Broadway, and the bar at the Knickerbocker Hotel, on the southeast corner of 42nd and Broadway, as “the headquarters of the 42nd Street Country Club.” “At the corner outside one heard for years only one phrase,” De Casseres plangently recalls: “ ‘Let’s have another.’” Nineteen twenty-five was, of course, the heart of Prohibition; and Mirrors of New York is a melancholy recollection of a vanished golden age. “The rapid fall of the booze forts around these corners and the rise of the chocolate and soda centers on their ruins is a matter of near history,” De Casseres writes, in what is possibly the earliest account on record of Times Square ruined by the forces of modernization and propriety.

The Eighteenth Amendment took effect July 1, 1919, but the Volstead Act, which made Prohibition national law, only went into force on January 16 of the following year. It was a bitterly cold night; the temperature dropped to six degrees. The drinking crowd jammed into the old booze forts like condemned prisoners partaking of a final meal. Reisenweber’s held a funeral ball; the waiters at Maxim’s were dressed as pallbearers. For all the chin-up insouciance, the metaphor was no joke for the establishments themselves. Without alcohol, the great lobster palaces felt like overupholstered mess halls. Who would linger until the late hours over a carafe of ginger ale? Within three years, every single one of the great old Broadway restaurants had disappeared. And in their place came the hot dog stands and soda fountains and “coffee pots” that disgusted the likes of Benjamin de Casseres. Prohibition annihilated the splendid eating and drinking culture of Times Square.

What it could not annihilate, of course, was drinking itself; that was much too deeply ingrained in the life of the place. And so drinking changed, almost overnight, from a beloved pastime, like dancing or playgoing, to a clandestine and fugitive act. Within a few years there were hundreds, if not thousands, of speakeasies in the area around Times Square. Most of them were located not in the grand open spaces formed by the convergence of the avenues, as the lobster palaces had been, but in brownstones, and above restaurants, and behind shops, on the cross streets of the Forties. Many of them were just underground versions of the cheap bars that had flourished in the area for years; the patron would show a familiar face or mention a familiar name, or even mumble a password through a sliding window or a barred opening in the door. Others were private homes, where drinkers would be escorted into what had once been the living room of an apartment. Some of these establishments—the kind you might read about enviously in The New Yorker— offered copies of the latest magazines, and soft armchairs, and legitimate Scotch highballs. Others—a great many more—reeked of yesterday’s Welsh rarebit and watered their gin and padded their bills, and occasionally robbed a customer too drunk to notice. A. J. Liebling once wrote a story in The New Yorker about sign painters who had made a fine living during Prohibition instantly repainting nightclubs and shifting around the furniture, so that when outraged patrons returned the next day with the police the place was unrecognizable, and they doubted their own fuddled memories.

A speakeasy was a criminal establishment, like an opium den. The cop on the beat could usually be paid off to look the other way, but the more intrepid and relentless federal agents were raiding bars and nightclubs, smashing the bottles, padlocking the establishment, and carting off the owners and the staff to jail. Most patrons, and most owners, considered the raids a nuisance and an occupational hazard; Prohibition made absolutely no moral headway among the sophisticates and devout drinkers of Broadway. If anything, Prohibition had the effect of discrediting sobriety itself; the mild risk associated with drinking only made the act more chic. And the almost complete separation of eating and drinking probably also had the effect of promoting drunkenness.

But speakeasies rested on another and more serious species of illegality, for the trade in bootleg liquor was almost entirely controlled by organized crime. Rum-running essentially created organized crime in New York and Chicago, just as the rise of the drug trade in the 1960s and after fostered the rise of new criminal cartels. The great underworld figures of the day—Dutch Schultz, Owney Madden, Lucky Luciano—were first and foremost bootleggers. And they plowed their wealth back into Times Square in the form of nightclubs, which were speakeasies with entertainment. Virtually all the famous nightclubs of the day—the El Fey, the Silver Slipper, the Hotsy Totsy, the Parody—were partly or wholly owned by gangsters. “It was a setup made to order for mobsters,” as Nils T. Granlund, the foremost producer of nightclub acts, writes in his memoir, Blondes, Brunettes and Bullets. The mobsters were already supplying the alcohol, they had access to enormous supplies of cash, and many of them loved nothing more than hanging out at the clubs.

“At its best,” wrote Stanley Walker, the famous city editor of The New York Herald, “the night club, in all senses, was a poor imitation of the spacious, clean-aired cabaret; at its worst it was horrible—a hangout for thugs, cadets, porch-climbers, pickpockets, halfwits, jewel thieves, professional maimers, yeggmen, ex-convicts and, in its later days, adepts at kidnaping and ‘the snatch racket.’” The nightclub was an underworld; that very fact made it deeply attractive to the newspapermen and ballplayers and chorus girls and instant millionaires who took a dim view of respectability, or at least wanted to dip their toes in the disreputable. And it was this mixed crowd, and this clandestine culture, that was the source of the raffish Times Square of the Roaring Twenties that the whole world came to know thanks to the writing of Damon Runyon, Walter Winchell, Mark Hellinger, and the other great newspapermen of the age. Not for nothing did Stanley Walker refer to the twenties as the Nightclub Era. The nightclub was the subterranean stage of this self-consciously theatrical age. While the cosmopolitan wit of Kaufman and Woollcott and Benchley played out on the public stage of the theaters, the ribaldry and hijinks and gunplay of the nightclubs created a private—and for that very reason glamorous—stage of its own.

NILS T. GRANLUND, who was in a position to know, opined that every nightclub on Broadway in the early years of Prohibition was essentially a bordello with music and dancing. The first generation of clubs, like the old concert saloons, catered to men who wanted to get stiff as a board and to men who wanted to buy sex; the waitresses were essentially on their own when it came to making money off the clientele. The clubs rarely had the resources to afford serious entertainment, and the gangsters who owned them were in the habit of aiming low. The first classy nightclub was the El Fey, which opened in 1924. The club’s owner was Larry Fay, a bootlegger and taxi fleet operator who owned the taxi concessions at Grand Central Terminal and Penn Station. (It was widely understood that the second job required a good deal more ferocity than the first.) But the real force behind the club, and then behind a succession of clubs bankrolled by Fay and other gangsters, was a faded silent-movie star who called herself Texas Guinan. Tex, who at the time was forty, was a big, buxom woman perpetually swathed in diamonds and pearls, a florid, funny, loudmouthed, lovable character much like her near contemporary Mae West. And she was just about to become the whirling center of the new nocturnal culture—“the Queen of the Nightclubs.”

Tex presented herself to the world as a cowgirl who found that she loved the lampposts of Broadway better than the stars of the big sky— a sort of Annie Oakley–turned–Sophie Tucker character. She said that she had been raised on a fifty-thousand-acre ranch in Texas, that she had run away with a rodeo circus, that she had knocked around the Colorado mining towns. A biographer, after much patient research, concluded that all of these claims were fabricated. Tex had a relatively genteel upbringing in Waco and Denver, and then around 1907 became a vaudeville performer and a second banana in light operas along Broadway. Trifling with the strict truth in such matters was considered, at the time, an entirely laudable proof of imagination, but the fact that Tex chose to invent a Wild West background for herself says a good deal about life on Broadway. In the demimonde, or perhaps hemidemimonde, that she occupied, certain western ideals—the ability to handle yourself with your fists, to spin a yarn, to live by your wits—became strangely mixed with the sybaritic nighttime world of the big city. A faint tang of the mining camp clung to the nightclub.

Tex perfected her two-gun persona in silent movies like The Gun Woman. She did all her own stunts and was known as “the personification of female daredeviltry.” In 1921 she formed her own production company, planning to churn out a series of two-reelers—Texas of the Mounted, The Soul of Tex, The Claws of Tex, and so on. The venture never quite panned out, and Tex returned to New York, from which she had never been absent for long. Nils Granlund claimed that he discovered her emceeing a show at a club called the Beaux Arts, and introduced her to Larry Fay, an upwardly mobile gangster. In 1924 he opened up the El Fey—no one ever knew why he chose to misspell his own name—with Tex as hostess. The club, on 45th Street between Sixth Avenue and Broadway, was a tiny room located at the top of a narrow staircase and behind a door with a peephole cut into it. Most of the chorus came from the Ziegfeld Follies at the New Amsterdam; the girls came over after the show closed up at eleven. Some were as young as thirteen, and Tex served as their mother hen. There was no soliciting in either direction at the El Fey; some of the girls said later that they never heard so much as a cussword. The customers knew they would have to answer to Tex for any infractions of the rules.

Tex herself generally breakfasted some time before midnight, and arrived at the club around one. The girls would often come out and sing “Cherries,” and while they sang they would pass through the crowd picking cherries from a basket and popping them into the mouths of customers, who would beg for a cherry. (The rule against soliciting did not extend to titillating.) Then Tex, who had a voice of brass, might get up on a chair and lead the crowd in a rousing version of an old standard, like “California, Here I Come.” Thereafter, she would sit in the middle of the crowd, teasing and heckling her customers, inveigling the more demure among them into playing leapfrog and other silly games, and sometimes blowing on a police whistle to get attention. Arriving customers were greeted with the cry “Hello, sucker!,” a tacit acknowledgment that they were about to be fleeced by Tex’s ludicrous prices—$25 for a bottle of “champagne” that consisted of cider spiked with alcohol—and an act of welcome to the community of suckers, which included Tex herself. When a visiting dairy magnate spread his cash around particularly thickly, Tex shouted, “Here’s my big butter-and-egg man!,” coining the phrase that George S. Kaufman lifted for the title of his play—or so the legend goes.

Tex was a wisecracking, extravagant Dame of Misrule. Edmund Wilson described her as a “prodigious woman, with her pearls, her glittering bosom, her abundantly beautiful bleached yellow coiffure, her formidable rap of shining white teeth, her broad bare back behind its grating of green velvet, the full-blown peony as big as a cabbage exploding on her broad green thigh.” With her gleeful contempt for propriety, her ready wit, her love of the rollicking good time, her world-weary wisdom, Tex came to be viewed as an incarnation of the age—a sort of one-woman Algonquin Round Table. Paladins of high culture like Wilson made pilgrimages to her throne, and the highest of nobility paid her court. Tex claimed Edward, Prince of Wales, as one of her dear friends, and said that when she was raided one time she told the prince to hustle back into the kitchen and start frying eggs; Lord Mountbatten, on the other hand, she disguised as a drummer. The battle for the high ground between Tex and the authorities was strictly no contest.

Tex never stayed in one place for long. The police closed down the El Fey in April 1925, and Tex reappeared at the Texas Guinan Club on West 48th Street. The club was busted after four months, and then Tex popped up again at the Del Fey, back in the old spot on 45th Street—a calculated act of insouciance. Later she moved on to the 300 Club, the Club Intime, and the Club Argonaut. The New Yorker, which chronicled Tex’s doings, once noted that “the occasion of Texas Guinan’s 3,465th opening occurred, this time at 117 West Forty-eighth Street, where she was two summers ago.” Tex laughed at enforcement; and all New York, or so it seemed, laughed with her. When she was arrested in early 1927, the crowd spilled out onto the street while the band mournfully played “The Prisoner’s Song,” a big hit from 1924. When the city passed a draconian piece of legislation known as the Padlock Law, Tex put on “The Padlock Revue,” and swanned around her latest club in a necklace of padlocks. Finally subjected to a sort of show trial in 1928, Tex insisted that she had never owned any of her places, that in any case she had no idea liquor was being served, that her good name was being trampled in the mud, etc. The trial was a tabloid sensation, and the unsinkable Tex was finally cleared of all charges.

Tex’s various clubs were the Rector’s of the Prohibition era—the spot where the life of the place was most intensely led, where the true denizens of Broadway passed their idle hours while awestruck out-of-towners enjoyed a taste of the real thing and collected an anecdote or two to bring home. Tex knew everyone and everything. Reporters found her a precious resource. Heywood Broun of the World would drop by, and Mark Hellinger of the Daily News came almost every night with his young friend Walter Winchell. Winchell was a former vaudevillian, like Tex, who had spent years knocking around small-town theaters with a song-and-dance act known as Winchell & Green. He had begun his writing career by tacking typewritten sheets in the lobby of a theater with news items about the performers appearing that night. Then he had landed a job with Vaudeville News, a bit of puffery published by the Keith-Orpheum vaudeville circuit from the company’s headquarters in the Palace Theatre. Since virtually the entire world of vaudeville was concentrated in a two-block radius around the Palace, Winchell came to possess a microscopic knowledge of this knockabout, baggy-pants world. He did not, however, have much acquaintance with the beau monde, and in 1924, when the El Fey opened up, Winchell had just landed a job as a gossip columnist— a term that did not yet exist—at a dreadful little newspaper called TheGraphic.

Winchell was, as Stanley Walker put it, “an astonishingly alert, electrically nervous little man,” fast-talking, indefatigable, avid. His biographer Neal Gabler writes, “He smoked furiously, gabbed incessantly, scribbled quickly (usually with a stubby pencil on the back of envelopes or on a folded square of newsprint) and drummed the table with his fingers on the rare occasion when he wasn’t talking.” He would hang around the speakeasies, and if he heard a burst of laughter from a table he would race over and cry, “What’s the gag? Is it anything for the column?” Tex was, in the early days, his mother lode. Winchell would often spend the entire night at one of her clubs, playing poker and swapping stories with her and Hellinger after the place closed up, at three or four in the morning. Later on, Winchell would say that it was Tex who gave him the idea to write about society folks, because she would point around the room and say that this one was having an affair with a chorus girl, and that one was about to get married, and the other one had just come back from Reno. And Tex knew the gangsters every bit as well as she knew the party girls.

Winchell’s obsession with ephemera, his breathlessness, his hokey neologisms, made him something of a joke with the soigné crowd who hung around Neysa McMein’s studio; but he would ultimately become a bigger figure than any of them. Winchell’s education ran through sixth grade, and he aspired to nothing greater, or lesser, than to tell the secrets of Broadway, which he described variously as “The Main Stem,” “The Street of Broken Dreams,” “The Clogged Artery.” A nation that was as besotted with Broadway as he was couldn’t get enough of Winchell’s news. By the late 1920s, when he had left The Graphic for the far more reputable Mirror, Winchell was one of the most famous newspapermen in the great age of newspapermen. And then his stupendously popular radio show, which he began broadcasting in 1930, lifted him to a level of celebrity all his own. Winchell became the Mayor of Broadway, the Bard of Broadway, the Boswell of Broadway. He described a world where everybody had something going on the side—an affair, a racket, a dark secret. And he defined as well the tough-guy ethos of a crowd that lived by its own rules. “At that other table is a horse from a different stable. The woman with him isn’t his wife. . . . His wife is in a 46th Street hideaway right now with The One She Goes For. Got it? . . . Must be terrible to be found out. . . . And a guy is a sap to wise a pal, too, even when he knows he is being crossed. . . . They never appreciate the tip.”

Winchell absorbed the gangster ethos, and the gangster language, of the nightclub world, and replayed it to America in his own peculiar patois—“a guy is a sap to wise a pal.” Winchell knew that whole crowd, and was particularly close to Owney Madden, who gave him a Stutz Bearcat. Madden, who was also a friend of Tex’s, owned one of her clubs along with his confederates Frenchy DeMange and Feets Edson. Winchell often passed along to his readers juicy bits of gossip about hoods that he picked up from Tex. In February 1932, he reported that “five planes brought dozens of machinegats from Chicago Friday” in order to rub out Vince “Mad Dog” Coll, a feared hit man who had been reckless enough to kidnap DeMange and extort a ransom from Madden. When Coll was murdered in a phone booth that very night, Winchell was targeted for revenge—the hoods feared he would be forced to talk to the DA—and it may only have been his relationship with Madden that saved him.

Winchell was at once a creature of Broadway and a student of Broadway. He loved the big names, but he was too much the ex-hoofer to have stars in his eyes. Broadway, he once wrote, “is a hard and destructive community, even for those who ‘click.’” He would later become a baroque figure, a great friend of J. Edgar Hoover and a notorious red-baiter, less a teller of tales than himself the tale; but as a young man, hopping from one speakeasy to the next, he “caught the tempo of New York in the late twenties and early thirties,” as Stanley Walker writes. “The tempo was brittle, cheap, garish, loud, and full of wild dissonances.”

Texas Guinan ultimately became such a byword for Broadway nightlife that she starred in her own movie, Queen of the Night Clubs, in 1929, and enjoyed several stints as a celebrity journalist. Her column, “Texas Guinan Says,” appeared daily in The Graphic. She put three dots between her items, just like Winchell, producing the same breathless, jazzy sense of experience caught on the fly. She tossed off a rapid-fire sequence of cracks and tough-guy asides: “There are far too many women who act like they were born in revolving doors—they are so dizzy and keep going around in circles.” And she was a name-dropper to put anyone but Winchell in the shade, managing to include, in the space of about 250 words, Woodrow Wilson, Herbert Hoover, Benito Mussolini, Primo Carnera, David Belasco, Heywood Broun, and Ethel Barrymore— although, to be fair, it’s unlikely that Wilson, who died in 1921, visited any of Tex’s clubs.

Tex comes down to us today chiefly through the works of Damon Runyon, the other and more lasting bard of Broadway in the nightclub era. Runyon’s girlfriend Patrice Gridier was in Tex’s chorus in 1925, though it is safe to say that he would have gravitated to Tex’s clubs in any case. Tex was a natural-born goddess of Runyon’s scruffy Olympus. One of his most famous stories, “Romance in the Roaring Forties,” written in 1929, concerns not only Tex but Winchell, whom Runyon normally treated as somewhat below his level of regard, but who served perfectly as a Broadway type. Runyon barely deigned to disguise his characters: “Romance in the Roaring Forties” opens in the “Sixteen Hundred Club” of “Missouri Martin,” “an old experienced doll” known as “Mizzou” who “tells everything she knows as soon as she knows it, which is very often before it happens.” The story concerns a gossip columnist named Waldo Winchester who falls in love with Billy Perry, the girlfriend of a gangster named “Dave the Dude,” whom Jimmy Breslin, in his luminous but hallucinatory biography of Runyon, identifies with the Mafioso Frank Costello. The story’s narrator treats Waldo as an unaccountable idiot for having placed his life in jeopardy over a girl; and Mizzou tells Billy that she is “a little sap” for falling in love with a starving newspaperman when “everybody knows that Dave the Dude is a very fast man with a dollar.”

“Romance in the Roaring Forties” is, like so many Runyon stories, a kind of extended joke, because the violence for which the reader is being continually prepared not only never occurs but collapses into rank sentimentality. Rather than obeying his initial impulse to murder Waldo, Dave arranges for him to marry Billy because, he tells the narrator, “I love her myself so much that I wish to see her happy at all times, even if she has to marry to be that way.” And then, when it turns out that Waldo is already very much married and was only trifling with Billy, rather than murdering Waldo a second time, Dave turns around and marries Billy himself. Dave has a heart of gold; and he is still, of course, a ruthless killer. The story never loses its hard-boiled edge because we know perfectly well that marriage will not “reform” Dave. And it probably won’t reform Billy, either. But of course only a sap would suggest as much to either.

Runyon’s Broadway, like Winchell’s, was a comic rather than a tragic place, a place full of wild incident, a place where the normal human motives are much easier to read because the citizens prefer to do without the usual layers of hypocrisy. It is a very far cry from the Broadway of Julian Street or Rupert Hughes—not because the place has degenerated, but because it has become impossible to imagine a morally superior alternative. Some combination of Prohibition with the generational contempt for received proprieties has so completely discredited conventional norms of behavior that an honest cynicism, combined with the threadbare sentimentality of a dying hood who falls in love with a lame dog (another Runyon tale), has become the local ideal of nobility. A guy is a sap to wise a pal.

Runyon was, like Tex, a western migrant to the big city. He was born, by an amusing coincidence, in Manhattan, Kansas, and as a small-town newspaperman he had knocked around the western mining camps— usually reeling drunk—that Tex could only boast about. Runyon wasn’t a florid person, like Tex; he was one of those devastatingly funny people who almost never smile, which is to say that he could be a very disconcerting person. His stoicism, his tough-mindedness, his contempt for the straight and narrow, and his storytelling gifts made him an appealing figure among the hoods and horseplayers and reporters with whom he invariably hung out. Runyon only arrived in New York in 1910, when he was twenty-six. In 1914 he landed a job at William Randolph Hearst’s American, where he remained as sportswriter, feature writer, and columnist until 1928. When he wasn’t in Florida for spring training, or in Chicago for a fight, he could normally be found within the confines of Times Square.

Though Runyon was at least as much a Broadway character as George S. Kaufman or anyone in his circle, one finds very little reference to him in their writings, or to them in his. They occupied different Times Squares, for by this time Times Square had become such a capacious, such a various, place that it could accommodate several very different cultures and could conjure up to the rest of the world a very mixed set of images and associations. There was a lighthearted, witty, and urbane Times Square, and a roguish, slightly sinister Times Square. And this truth was expressed geographically, for Runyon’s Times Square, both the one he wrote about and the one he lived in, was a micro-neighborhood located well to the north of Kaufman’s theatrical world, which was concentrated in and around 42nd Street.

A new Madison Square Garden had gone up in 1925 on Eighth Avenue between 49th and 50th Streets; and the sports fans and promoters and ticket agents and bookies who went to the Garden for prizefights and college basketball games and bicycle races and wrestling matches hung out at the hotels and bars immediately to the east. The sidewalk on the east side of Broadway between 49th and 50th was known as Jacobs Beach, because the fight promoter Mike Jacobs and his pals were wont to camp out there. Both Winchell and Runyon frequently dropped in on the crowd there for local tidings; both men also lived for a time in the rooms above Billy LaHiff’s Tavern on 48th west of Seventh, as did Jack Dempsey and the columnist Bugs Baer. Runyon later removed to the Forrest Hotel, a block to the north, which also hosted the innumerable assignations of the boxer and heartthrob Primo Carnera. Texas Guinan’s various clubs were never more than a few blocks away, and the other great nightclubs of the time, including the Hollywood and the Silver Slipper, were virtually next door. Here was a vast, teeming world that extended no more than a thousand feet in any direction.

If Walter Winchell was Broadway’s town crier, then Damon Runyon was its griot and its folklorist-in-chief. Runyon gave the world a Broadway that was infinitely dense with incident, and yet scaled down to the size of a village. It was an intricate little place where people walked from here to there, saluting their friends and experiencing chance encounters that not infrequently led to their death. “One night,” Runyon writes in “The Brain Goes Home,” “the Brain is walking me up and down Broadway in front of Mindy’s restaurant, and speaking of this and that, when along comes a red-headed raggedy doll selling apples at five cents per copy. . . .” In other stories, the narrator isn’t even going anywhere; he’s just standing outside Mindy’s front door when the neighborhood characters come waltzing down the street, and soon another adventure has begun.

Runyon’s geography was subtly different from Winchell’s. With the help of guides like Tex, and thanks to his own burning ambition, Winchell had left behind the vaudeville shtetl of 47th Street for the beau monde of the clubs and cabarets. But it was just this side-street world, whose denizens gazed yearningly at the blazing lights of Broadway, that interested Runyon. For all his tough-mindedness, Runyon was a sucker for little people with hopelessly big dreams; he wrote about them with a pathos Winchell never could have mustered. In fact, he christened the block behind the Palace Theatre “Dream Street.” There, he wrote, “you see burlesque dolls, and hoofers, and guys who write songs, and saxophone players, and newsboys, and newspaper scribes, and taxi drivers, and blind guys, and midgets, and blondes with Pomeranians, or maybe French poodles, and guys with whiskers, and nightclub entertainers, and I do not know what else.” And all of them “sit on the stoops or lean against the railings of Dream Street, and the gab you hear sometimes sounds very dreamy indeed. In fact, it sometimes sounds very pipe-dreamy.” It is no coincidence that after this epic evocation, Dream Street Rose, the living soul of the street, tells the narrator a tale about a young woman—herself, in days gone by—in the mining town of Pueblo, Colorado, another burg full of stranded souls dreaming of the big strike that will set them free.

It is a crucial part of Runyon’s mystique that it is almost impossible to say where life ends and literature begins. You cannot read the Broadway stories without imagining Runyon himself as the all-knowing, deadpan narrator—the fellow who modestly says he “gets about.” Runyon, of course, got about. Keeping approximately the same hours as Winchell or Tex, he would emerge from LaHiff’s or the Forrest in the early afternoon, join the crowd at Jacobs Beach, and then wander inside to his table immediately to the right at the front of Lindy’s, the “Mindy’s” of his stories. Lindy’s was to Runyon what Texas Guinan’s clubs were to Winchell: the place where the stories he wanted to hear were told. Runyon would sit there for hours with Nils T. Granlund, or with Carnera or Dempsey, or with various small-time gangsters, or with Arnold Rothstein, the model for the Brain.

Rothstein, who controlled the poker games and the floating craps games along Broadway and elsewhere in the city, was a legendary figure in Times Square, a soft-spoken and mysterious character who seemed accountable to no one. In The Great Gatsby, Fitzgerald names him Meyer Wolfsheim and recounts the widely believed tale—since discredited—that he had fixed the 1919 World Series. Fitzgerald’s Rothstein is a silken monster who proudly shows Nick Carraway his cufflinks: “finest specimens of human molars,” he brags. Indeed, the dark revelation at the heart of the novel is that Jay Gatsby works as a bootlegger for Wolfsheim and owes his entire fortune to him. In Rothstein are concentrated all the dark forces that lie below the wild gaiety of Fitzgerald’s novel.

Runyon, by contrast, was friendly with Rothstein, as he was with Al Capone, Owney Madden, Frank Costello, and virtually every other important hoodlum of the day; and he turned them all into “characters.” Runyon knew very well what they were, but he had too dim a regard for legitimately constituted authority to judge them according to their deserts; besides, he had business transactions with several of them. Runyon and a few of his buddies were with Rothstein in Lindy’s the night of his death—one of the great set pieces of the journalism of the day. Rothstein used Lindy’s as his telephone booth, and one night in 1928 a call came in for him. Rothstein listened, nodded, put down the phone, handed his gun to a friend, and went out into the night. Everyone sitting there knew that he had become a hunted man after failing to pay a quarter of a million dollars in gambling debts. It was a moment of the kind of high stoicism Runyon cherished in his Broadway characters—a moment when Times Square turned into the O.K. Corral. Several hours later, Rothstein, riddled with bullets, stumbled out of the elevator of a Central Park West apartment building. He lived for several days, refusing to breathe a word about his assailant.

TIMES SQUARE IN THE Roaring Twenties was both the sparkling world of the Algonquin Round Table and the yeggs’ kingdom of Owney Madden—“Owney the Killer.” And though these may have been more parallel than overlapping worlds, each lent its atmosphere to the other. It was the sparkle of the age that made the gangsters so glamorous; it was the lurking brutality of the age that gave the drama its edge of menace. Perhaps the single most famous play of the decade was The Front Page, a story about gangsters, cops, killers, and reporters written by a pair of hard-boiled newspapermen. It was an era that thumbed its nose at authority and turned lawbreaking into a charming adventure. Even the city’s mayor, James J. Walker, was a figure out of Runyon—a dandy, a wit, a barfly, a friend to all, a faithless husband, and a veteran of Tin Pan Alley who never missed a heavyweight bout or a new nightclub act. A biographer called him “the John Barrymore of the political stage.” Walker ordered the police to stop enforcing Prohibition, and deprecated all forms of moral crusading with the sarcasm of a true New Yorker. Placing himself in opposition to a piece of censorship known as the Clean Books Bill, Walker famously declared, “I have never yet heard of a girl being ruined by a book.”

And then the bubble burst. First came the Depression, though it would take several years of hard times before people stopped buying tickets to shows or peeling off twenties in nightclubs. And then came the repeal of Prohibition, in 1933. Repeal killed many of the clubs, just as Prohibition had killed the lobster palaces. And it forced the mobsters to find less glamorous precincts in which to ply their trade. Jimmy Walker finally had to resign in 1932 after an investigation documented his habit of exchanging city contracts for quite large personal gifts; the new mayor, Fiorello La Guardia, vowed to clean up the town, and did. Florenz Ziegfeld, whose career had begun in the previous century, died in 1932—penniless, of course. Larry Fay was murdered by the doorman of his latest club in January 1933. And Tex, whose star had been dwindling since the late twenties, died later that year in Vancouver. She and the girls had been booted out of Paris for indecency, and Tex had then mounted a show called Too Hot for Paris, which turned out to be too hot for the hinterland as well. She had then bounced around Chicago, and had died on a western swing.

Tex’s demise received the kind of newspaper coverage once given to the deathwatch over J. P. Morgan. Her obituary appeared on the front page of many of the New York papers, and she was recalled as the very emblem of a world already receding into memory’s mists. Walter Winchell did not stint on behalf of his old muse. “We learned Broadway from her,” he wrote. “She taught us the ways of the Street.”

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