I Love This Dirty Town

Sweet Smell of Success, Swing Street, and the Voices and Vices that Made Mid-century Manhattan

EDITOR’S NOTE: This article is the first chapter of my book, Cocktails and Capers: Cult Cinema, Cocktails, Crime, & Cool. Before that, various bits and pieces appeared in articles scattered across Alcohol Professor. On Dec 11, 2020, the 21 Club announced that it was all over. Changing times and COVID-19 did what Prohibition couldn’t do. They’re just one among many stories that have ended this year, from grand old institutions to fantastic little holes in the wall, the pandemic has taken a brutal toll on restaurants, bars, and the people who depend on them for a living. If you have some extra, considering donating to the Restaurant Employee Relief Fund.

It’s after dark, when the city is at its best. We drift through the desperate, glorious chaos of New York at night, to the brassy, aggressive strains of a jazz anthem composed by Elmer Bernstein. Men in suits and women in cocktail dresses stumble into and out of cabs, into and out of nightclubs. People who want to be seen, people who want to see. Movers, shakers, power players, hustlers, hyenas. The kings and queens, the wannabes, the has-beens, the never-will-be’s. Our eye is the lens of James Wong Howe’s camera, in moody, beautiful black and white and at a depth-of-focus that is overwhelming, like the city at night. Too many people. Too many cars. Too many blinking neon signs. There’s too much too see. Too much. And never enough.

Through these dangerous waters that stink of booze and cigarettes and perfume swims J.J. Hunsecker, a merciless, emotionally-remote gossip columnist who can make or destroy a career with a single sentence—and who relishes that power of professional life and death. Around him swirls a cloud of sycophants looking to make themselves seem more impressive by association or looking to catch J.J.’s eye so that he might throw a kind word the way of their new play or new client. In the middle of the pack—and dreaming of leading the herd—is Sidney Falco, a hungry press agent with no morals, a man willing to pull any con, use anyone, hustle any way he can to claw his way out of mediocrity. Hunsecker is Sidney’s ticket out of the bush leagues. Hunsecker knows that. And Hunsecker isn’t the kind of man not to use it.

This is the world of Sweet Smell of Success, an acerbic showbiz noir from 1957 directed by Alexander Mackendrick and written by Clifford Odets and Ernest Lehman (who also wrote the novel on which the movie is based). It is one of the meanest films of the late noir era, full of cynical, misanthropic characters. It accomplishes this without gangsters, without shootouts, without murder or most of the accoutrements one usually associates with film noir. It is one of a handful of noir that focus on the cutthroat nature of the very business that created it: entertainment.

Burt Lancaster is the remorseless J.J. Hunsecker. Tony Curtis, in a role so slimy that his fans revolted against the besmirching of his good guy persona, stars as “anything to get ahead” press agent Sidney Falco. As J.J. says, “I’d hate to take a bite outta you. You’re a cookie full of arsenic.” They were both New York boys—Lancaster, from 209 East 106th Street in Manhattan; and Curtis, the son of a tailor from The Bronx—in one of the quintessential New York movies. Much of the film’s action takes place in two locations. The interiors were sets, but the exteriors and the locations were real. Sidney Falco throws himself into the sweaty, drunken crowd at the rowdy night spot Toots Shor’s. J.J., impeccably dressed and observing the world like a bird of prey, holds court in the estimable 21 Club. One of these places is gone; the other still stands in a city that always moves forward, the last remaining bastion of an area that once boasted jazz clubs and night clubs. Where the action was. The street that played host to the likes of Frank Sinatra and Billie Holiday.

They called it Swing Street.

52nd in Manhattan, when it was Swing Street

Nuttin’ Fancy

Just over half a century ago, in a Manhattan defined by sharp suits and three-Martini lunches, there was a joint called Toots Shor’s. It was the kind of place where Joe DiMaggio would go to enjoy a drink with Jackie Gleason; where Frank Sinatra would drop in to keep himself from brooding; where Marilyn Monroe could be found sitting at the famous round bar. Yet despite its place as one of the great celebrity watering holes of the Golden Age, it was no bastion of elegance. When they called it a joint, they meant it was a joint. Smoke and crowd and noise. Toots Shor, the man behind it, wasn’t a polished member of the aristocracy looking to foster the rarefied airs of café society. If Toots Shor’s was a cocktail, it would have been a whiskey sour. If it was food, it would have been “maybe you should eat somewhere else.”

I mean, yeah, they had a kitchen. It served up standard fare for a time when “fine dining” wasn’t very fine: shrimp cocktail, baked potatoes, Yankee pot roast. There’s a reason mid-century America is remembered for drinking, style, design, and architecture—but not cuisine. You didn’t go to Toots Shor’s for the food. You went for the atmosphere and the booze. Sure, you wore your suit and tie or your cocktail dress (wives were discouraged, though mistresses and “broads” were welcome—mid-century America isn’t celebrated for its cuisine, and it’s sure as hell not celebrated for gender politics.). But this place was all back-slapping drunks with their arms around each other…and occasionally their fists in each other’s faces. But only occasionally.

Toots was born in Philadelphia in 1903 to Orthodox Jewish parents who didn’t call him “Toots.” They called him Bernard. Both parents died tragically when Toots was young. When he was 15, his mother was killed in a traffic accident while she was sitting on the stoop of their apartment. His father went five years later. Suicide. Toots attended college, bounced into a job as a traveling salesman (shirts and underwear), and ended up in New York working the door at speakeasies. There, he met and befriended many of New York’s celebrities, politicians, and gangsters, all of whom came together for an illegal drink or two at places like the Five O’Clock Club and Lahiff’s Tavern. Gregarious, but capable of socking an unruly drunk when he needed to, Toots worked his way from the door to floor, then to manager, and finally to owner, when he opened his own place in the 1940s at 51 West 51st Street.

The celebrities he’d befriended over the years were happy to come along, especially when it became obvious that Toots was never going to call in their tab. Or even keep one. Through the 1940s and ’50s, Toots Shor’s was the place. Toots himself described it as “nuttin’ fancy.” An after-watering-hole watering hole. Jackie Gleason was practically a resident, showing up to drink away the afternoon, heading home for a nap (rumor had it he took an apartment in the same building so he wouldn’t have to walk far), then returning for the late-night scene. Sinatra name-dropped the place in “Me and My Shadow,” a duet with Sammy Davis, Jr., placing it alongside his other favorite hangout, Jilly’s Saloon. Judges, writers, stars, and mobsters flocked to Toots Shor’s, forming an inebriated brotherhood Toots lovingly referred to as “crum-bums.”

Toots Shor, Frank Sinatra, and Jackie Gleason

But above all others, Toots courted baseball players. Joe DiMaggio was a fixture, at least for a while. He stopped dropping by after Toots referred to Joe’s wife using a vulgar term for a lady of the night. Joe’s wife at the time being Marilyn Monroe. Joe and Marilyn split after less than a year of unhappy marriage. She wanted freedom. He wanted a housewife. Ugly though the split was, Joe never forgave Toots for insulting Marilyn. Not that he was any sort of dream husband for the blonde bombshell. His anger boiled over, left her bruised. After it all came unglued, DiMaggio sought companionship in Frank Sinatra—probably not the best drinking buddy at the time. Frank was a manic-depressive going through a serious depressive phase and a nasty break-up with Ava Gardner. It also probably wouldn’t have soothed Joe much to know Sinatra’s crew used Marilyn mercilessly.

Marilyn died in 1962. By 1962, Toots Shor’s was also gone, or at least relocated. It turned out that no matter how packed your place is, if you’re not making anyone pay their bill, it’s hard to pay the bills. Toots had to sell the 51st Street location in 1961, but he landed on his feet. Toots Shor’s reopened at a new location, 33 West 52nd Street. It was an address with a storied, perfectly sordid past as a place called Leon & Eddie’s, opened by entertainers Eddie Davis and Leon Enkin. It was one of the most infamous places along what became Swing Street but was then known as Strip Street. Toots himself had even worked there in the 1930s. Leon & Eddie’s catered to American servicemen looking for one last, memorable fling before shipping out to the War. Naked chorus girls, ribald stand-up comedians, and flirtatious dancers were happy to send the boys off with a smile that would last them to Berlin.

After Prohibition, some speakeasies going legit sought to cultivate an elegant clientele of celebrities and “café society.” Leon and Eddie’s, however, was the place local businessmen, adventurous tourists, cheap hustlers, and soldiers went to collect a secret, “a place where they didn’t have to worry about getting the high hat” as Billboard described it in 1946. Later, it became famous for regularly featuring two of America’s most celebrated burlesque queens: Noel Toy, a legend in the Chinatown nightclubs of San Francisco; and Sherry Britton, who peeled off clothes to Tchaikovsky and was made an honorary Brigadier General by President Franklin D. Roosevelt.

Just when Toots found himself out at 51st Street, Leon and Eddie were looking to call it a day. Shor, who had been a bouncer at the place in its speakeasy days, moved in. The new Toots Shor’s operated from 1961 until 1971, but the magic never returned. The late ‘60s and early ‘70s weren’t the ‘50s or early ‘60s. A turned-on, tuned-in young crowd was now in charge of defining the city’s sense of cool, and old cats like Toots weren’t able to run with the glitter and love brigade. He tried to franchise, selling the name to a management company that went on to handle TGI Fridays, but there just wasn’t much bank in a name like Toots Shor post-Sgt. Pepper’s. The space existed for a while as the New York, New York disco, home of the world’s first laser light show, until eventually the entire building was demolished. A massive glass and concrete high-rise looms there now.

Short of a whiskey and soda or Martini, about the only cocktail you’d order at Toots Shor’s was shrimp. Still, while researching the latest edition of the The Waldorf-Astoria Bar Book, writer/bartender Frank Caiafa came across a cocktail named in honor of Toots, though perhaps not with the character of the man or his joint particularly well reflected. According to Caiafa’s research, the “Toots Shor” as listed in the 1960 Calvert Party Encyclopedia was actually a Trilby No. 2 from the Savoy Cocktail Book, which already had a Trilby, even though the Trilby No. 2 probably predated the other Trilby, because it appeared in a 1900 manual by bartender Harry Johnson, where it was just called a Trilby. The history of cocktails is a nightmare. Whatever the case, the Toots Shor cocktails uses scotch, vermouth, Pernod, and Parfait d’Amour. The notion that Toots Shor would own a bottle of Parfait d’Amour, let alone drink it, is hilarious. But then again, who knows? Frank Sinatra painted himself up like a sad clown on one of his album covers. Those guys could contain untold depths.

The more suitable glass to raise in Toots’ honor is the whiskey sour, though it’s likely more than a few Rickeys and Gimlets got ordered at Toots Shor’s iconic round bar. The gimlet in particular has a storied past and a place of honor in the halls of hardboiled cocktails thanks to Raymond Chandler’s The Long Goodbye:

“We sat in a corner of the bar at Victor’s and drank gimlets. ‘They don’t know how to make them here,’ he said. ‘What they call a gimlet is just some lime or lemon juice with a dash of sugar and bitters. A real gimlet is half gin and half Rose’s Lime Juice and nothing else. It beats martinis hollow’.”

Rose’s Lime Juice was invented in 1867 by Lauchlan Rose as a way to preserve limes for the British Navy. The gimlet was invented when British Naval officers started mixing their daily dose of Rose’s Lime Juice with gin (non-officers mixed it with their rum and invented the first margarita). Why all the lime juice? The Merchant Shipping Act, also of 1867, required Navy vessels to provide a daily lime ration to sailors to prevent scurvy, a habit that earned British sailors the nickname “limeys.” Carrying Rose’s Lime Juice was much easier than hauling fresh limes around. Unfortunately, Rose’s Lime Juice (and limes in general) was terribly ineffective protection from scurvy.

It was believed at the time that acidity was what kept you from getting scurvy, so any sufficiently acidic fruit would do. This belief came about because in the mid-1700s, sailors who dosed their ration of grog (rum and water) with juice from citrus fruit were substantially healthier than other soldiers. This phenomenon was eventually attributed to the acidity of the fruit. Because the British Navy had easier access to limes than they did oranges or lemons, limes became the go-to—and didn’t do much of anything, especially once they had been processed into commercial lime juice. It wasn’t the acidity that was staving scurvy outbreaks; it was the vitamin C, and limes have very little vitamin C. Rose’s Lime had even less.

The Gimlet never really caught on in the United States, but Raymond Chandler’s hardboiled private detective, Philip Marlowe, enjoyed them (at least until tragic deaths spoiled his taste for the drink). Just as James Bond’s Vespers and shaken vodka Martinis cause debate, so too does Chandler’s recipe for a gimlet. His half-and-half proportions were likely because they were drinking rot gut gin. A saner ratio scales back the 50/50 scenario and uses better-quality gin. Just about everyone will tell you it has to be Rose’s, otherwise it is not a gimlet. As the 1954 Esquire’s Handbook for Hosts wrote, “A true Gimlet must be made with Rose’s bottled lime juice, which vanished like nylons during the war but is now seen around again.” But of course, what’s seen around now and what was seen around in then? It’s probable that Rose’s Lime today is not the same concoction it was.

So if you’re looking to stave off scurvy, keep dosing your grog with lemon and orange. But if you are just looking to sit in a corner booth in an old bar and enjoy a drink while you puzzle out the strands of a particularly convoluted case, the gimlet is there for you. Drink it under the same circumstances Marlowe’s doomed friend Terry Lennox prefers:

“I like bars just after they open for the evening. When the air inside is still cool and clean and everything is shiny and the barkeep is giving himself that last look in the mirror to see if his tie is straight and his hair is smooth. I like the neat bottles on the bar back and the lovely shining glasses and the anticipation. I like to watch the man mix the first one of the evening and put it down on a crisp mat and put the little folded napkin beside it. I like to taste it slowly. The first quiet drink of the evening in a quiet bar—that’s wonderful.”

Sinatra and Ava Gardner at Jilly’s

We’ll Wind up at Jilly’s Right After Toots Shor’s

West 52nd Street between Broadway and 8th Ave. is, today, one of those anonymous New York blocks that seems, at first glance, to offer very little other than the entrances to the Neil Simon and August Wilson theaters. But tucked beneath a nondescript red awning next to the buzzing neon Neil Simon sign is a piano bar and restaurant called Russian Samovar. The entrance is plain. The awning promises a “House of Flavored Vodkas,” which for some drinkers, is not an enticement, conjuring as it does chilling images of whipped cream or birthday cake-flavored shots of Smirnoff. The menu posted in the front window advertises traditional Russian fare: caviar and blini, salmon kulebyaka, vareniki, tabaka, beef stroganoff, and of course Chicken Kiev. Russia’s climate doesn’t inspire light, delicate victuals.

Russian Samovar opened in 1986, a partnership between three Russian expatriates: literature professor Roman Kaplan, famed poet Joseph Brodsky, and legendary ballet dancer Mikhail Baryshnikov. All three men considered themselves “fundamentally pro-Russian, yet vehemently anti-Soviet Union.” They wanted a place where like-minded artists could gather, talk, listen to music, and eat. Though most of the world didn’t realize it at the time, the Soviet Union was only a few years from dissolution, the Berlin Wall just a couple years from being overwhelmed and sledgehammered by jubilant Germans.

Before those momentous occasions, for many members of the Soviet diaspora who found themselves in New York, Russian Samovar became a home far away from home, where everything from politics to poetry was discussed over food and vodka.

The Soviet Union is gone now, but Russian Samovar is still there. Through the door, away from the crowd waiting to see Jersey Boys across the street, one is greeted by red boudoir lights, like something a saloon madam might have once hung in her cathouse. On the right is a long wooden bar behind which are arranged, among other liquors, some fifteen different house-infused vodkas. The vodka arrived in the 1980s, but the wooden bar has been there since the ’60s, when the place was called Jilly’s Saloon after its owner, Jilly Rizzo. Jilly’s was famous for a number of reasons, but two stand out above all others. One, it’s where someone once decided to murder Johnny Carson; and two, when Frank Sinatra was in New York, it’s where he would hold court, dining there several nights a week flanked by friends and associates while three waiters and Jilly himself ran interference on anyone hoping to drop by Frank’s booth without having been invited.

Despite being an icon of high living for generations, Sinatra was not a fan of haute cuisine. A high school drop-out from Hoboken, he was the only child of a lightweight boxer turned fireman and a political activist who ran an illegal abortion business that provided services for free. Even after he became famous, Sinatra preferred simpler fare and cozier surroundings than were found in the five-star restaurants of the world. There was P.J. Clarke’s at 915 Third Ave., where Sinatra carefully scheduled his nights to avoid gossip columnist Dorothy Kilgallen, whose favorite topic was anything going wrong in Sinatra’s life, especially if it concerned his tumultuous relationship with Ava Gardner. Then there was Patsy’s at 236 W. 56th St., where Frank ordered the breaded veal and spaghetti with red sauce on the side.

There’s a story about that place. As it goes, one Thanksgiving, Sinatra found himself on the skids, depressed, without company and without plans. So he made a reservation at Patsy’s, which wasn’t open that day. But owner Pasquale Scognamillo scrambled his staff and family so that when Frank rolled in at 3pm, the place was full. Rocky Lee Chu-Cho Bianco at 987 Second Ave was where Frank would go for pizza. And of course there was the spot on 52nd with the jockeys out front. But above and beyond them all was Sinatra’s affection for Jilly’s Saloon.

Don Rickles and Sinatra with Johnny Carson on the Tonight Show

Jilly was born Ermenigildo Rizzo on May 6th, 1917. His career in food services started early. He worked for his father, delivering Italian ice. He eventually opened his first restaurant, Jilly’s Saloon, on West 49th Street but later moved it to West 52nd, in the heart of Swing Street. It was this incarnation that attracted Sinatra’s patronage. On any given night when he was in town, he could be found at his regular booth surrounded by his regular friends. They would have received the call earlier in the day telling them to be there. Having grown up an only child, Sinatra swore he would never dine alone.

Jilly’s kitchen specialized not in Italian fare but in Cantonese food. Sinatra spent so much time there that Jilly became Sinatra’s closest friend, his right-hand man, and his bodyguard. By 1962 he and Jilly Rizzo were so close that Sinatra was securing bit parts for the saloon owner in films such as The Manchurian Candidate. That same year, Sinatra and fellow Rat Packer Sammy Davis Jr. recorded the duet “Me and My Shadow,” which twice mentions ending up at Jilly’s. He also name-dropped it in the 1968 song “Star,” in which he crooned “If they’ve got a drink with her name in Jilly’s bar, the chances are the lady’s a star.” In Sinatra’s 1968 detective movie Lady in Cement, he paid tribute to his long-time friend by naming a seedy Miami strip club after him.

Jilly’s was also famous as the spot where a mobster decided to murder comedian Johnny Carson. Inebriation had gotten the better of the funnyman’s judgment that night. He started flirting with a woman who’d caught his eye. According to Carson biographer Henry Bushkin, the popular funny man was doing his best to convince the young woman to leave with him. Unfortunately for Carson, that young woman was already spoken for by a jealous (and rather humorless) mobster. Enraged by Carson’s amorous intent toward the lady, the unnamed mobster and his crew roughed Carson up, even throwing him down a flight of stairs. It would have gotten uglier had Jilly Rizzo himself not intervened and cooled the situation down. Level heads prevailed only briefly, long enough for Carson to limp away. But he soon discovered that all was not forgiven. The mobster, still fuming, decided that night the world would be better off without Carson. A hit was put out on Johnny, who spent the next three days hunkered down in his room at the UN Plaza hotel, canceling multiple appearances and hoping things might simmer down.

They did eventually, but only after Carson cut a deal with crime boss and “civil rights activist” Joseph Colombo. Under the terms of his agreement with Colombo, Carson brokered a deal with NBC to cover Colombo’s Italian-American Civil Rights League Italian Unity Day rally. Mafioso Colombo formed the League to protest the stereotyping of Italian-Americans as a bunch of Mafiosos. The hit was called off, and Carson was free to resume his life. Colombo, on the other hand, was less fortunate. He was gunned down in 1971 during the second (and final) Italian Unity Day rally in Columbus Circle. The trigger man was a street hustler named Jerome Johnson, working presumably on orders from Vincenzo Aloi, right hand man of Colombo’s rival crime boss, “Crazy” Joe Gallo.

Colombo survived but was left completely paralyzed. He passed away in 1978 and was buried in Saint John Cemetery in Queens. Gallo was himself gunned down in 1972 while dining at Umberto’s Clam House (129 Mulberry St.). Coincidentally, Gallo, his family, and his crew had just come from seeing Sinatra’s favorite comedian, Don Rickles, at the Copacabana.

Umberto’s Clam House, site of one of New York’s most notorious Mob hits

Jilly’s wasn’t the kind of place that was going to last forever, not with the way they made a habit—not always by choice—of letting wise guys run up huge tabs without ever paying them. The passing of time inevitably faded the glory of the Rat Pack. By the 1970s, Tony Delvecchio, who had bought the place from Rizzo with a partner and done his best to keep it afloat despite changing times and unpaid tabs, had to shut it down. His experience running Jilly’s is detailed in a frequently-hilarious stream-of-conscious memoir titled Sinatra, Gotti, and Me. Jilly, who still served as the face of the bar, retired. The location ended up in the hands of Roman Kaplan, Joseph Brodsky, and Mikhail Baryshnikov.

Brodsky was born in Leningrad in 1940. As a child, he endured antisemitism, poverty, and the brutal siege of Leningrad during World War II. He was a rebellious kid who disliked the omnipresent images of Lenin that peppered the USSR. After dropping out of school, he drifted through a series of jobs and, in 1955, started writing poetry for an underground journal, Sintaksis. His fame spread rapidly, and for several years he enjoyed a great deal of success.

As success was wont to do during those paranoid years, it got Brodsky on the bad side of the government. He was denounced as a poor contributor to society, a pornographer, anti-Communist, and most outlandishly, “a pseudo-poet in velveteen trousers.” He was sentenced to five years of hard labor in the icy arctic north, only 18 months of which he served. Protests by prominent Soviet and foreign citizens secured his early release.

Contrary to the intentions of his rivals, Brodsky was fond of his time in the Arctic. He was invigorated by the labor and enjoyed the time for quiet contemplation, reading, and writing that the rustic isolation afforded him. After his return to Leningrad, he continued to write and continued to rub authorities the wrong way. In 1972, the Soviet government strongly suggested that Brodsky would be happier in Israel or, really, anywhere other than the USSR. Brodsky disagreed, stating flatly that he wanted to stay in Leningrad. Less than two weeks later, the government again suggested that he leave the country—this time by burglarizing his home, stealing all his papers, and forcibly placing him on a plane bound for Vienna. Having no interest in Israel or England, the exiled poet settled in the United States.

As Brodsky was being hustled onto a plane by the KGB, his countryman Roman Kaplan was boarding a plane for Israel with no intention of coming back to the Soviet Union. Kaplan, like Brodsky, was born in Leningrad around the same time (1938) and endured many of the same hardships during the war. He moved to Moscow and became a professor of American English and literature. By the 1970s, he was ready to live somewhere less oppressive. Eventually, Kaplan found himself in New York, where his passion for Russian art led to a job in a gallery. At the gallery, he met many prominent people, including Russians who were, like him, exiled from their home, their culture, and their food. Inspired by this, Kaplan opened his first restaurant, Kalinka, in 1984. In 1986, he sold Kalinka and opened a new restaurant at 256 W 52nd St., moving into the former home of Jilly’s. His contacts in the art world brought two business partners into Russian Samovar. One was Brodsky. The other was the most famous ballet dancer in the world. In 1974, Mikhail Baryshnikov, defected while in Toronto. In 1986, Baryshnikov became a naturalized citizen of the United States and agreed to get involved with Russian Samovar. In 1987, Brodsky won the Nobel Prize in Literature and invested the earnings into his friend’s new restaurant, a friendly, open space that would encourage art and expression.

Mikhail Baryshnikov

Kaplan read about the process of infusing vodka with flavors in old Russian texts and decided to introduce an infused vodka bar in the restaurant, a trend that would be copied by many bars and restaurants and that shouldn’t be blamed for the proliferation of birthday cake vodka. Infused vodka may be easy to find these days, but in 1986 when Kaplan got the idea, it was still a new concept in the U.S. Originally fabled to be aphrodisiacs (isn’t everything?), Kaplan and his bartenders encourage drinkers to consume the vodka the traditional way: with a compliment of pickles.

Though the restaurant has been around for decades now, Roman Kaplan still eats at Russian Samovar regularly. Enthusiastic and welcoming, with a wizened face lined by a fringe of well-groomed facial hair, he’s no hands-off owner. He’s there almost every night. There’s still music at Russian Samovar, and Frank’s table is still there, though few customers are aware of the role the spot once played in the life of the Chairman of the Board. If you want to talk about the history of the place, Kaplan will make time over the sounds of diners and live music. It might not be Sinatra, but the music is lively.

Jilly Rizzo, retired and moved to Palm Springs but still living the sort of life that led to things like a 1991 conviction for fraud (for which he was sentenced to 1000 hours of community service), was killed on May 6, 1992—his 75th birthday—when his car was struck by a drunk driver. Joseph Brodsky passed away in 1996 of a heart attack at the age of 55.

While vodka may be the star attraction at Russian Samovar, if you want to raise a glass to Sinatra, his “gasoline” of choice all those years was bourbon: four ice cubes, two fingers of Jack Daniels, and a splash of water. And if you were the type to “well, actually…” Sinatra about Daniels—he never called it “Jack”—being Tennessee whiskey and not bourbon, you’d soon get acquainted with the sidewalk out front of Jilly’s Saloon with a gruff warning from Jilly that it’d be in your best interest not to come back. But don’t worry. Swing Street had plenty more to offer than a chance to gawk at Frank Sinatra eating sweet and sour chicken.

Lady Sings the Blues

There are few moments more perfect than walking into a dimly-lit bar late at night and hearing a Billie Holiday song. “These Foolish Things” is practically custom-made for sliding onto a stool and ordering an Old Fashioned as you prop your elbows up on the bar and think about lost loves and life’s regrets. Her discography is not composed entirely of anthems for the lonely, but few American artists seem to have captured the melancholy of 2 a.m. quite like the woman who would become known as Lady Day. For much of her career, her unique voice could be heard in one of the many clubs that used to line Manhattan’s 52nd Street, that stretch of the city once known as Swing Street.

Verifiable details about Holiday’s life before her stardom are scant. Her own autobiography is vague and riddled with inconsistencies (it was, in fact, written by a man named William Dufty, and when questioned about some obvious errors in it, Holiday famously shrugged and said “I ain’t never read that book.”). She was born Eleanora Fagan in Philadelphia and raised in Baltimore. Her father split, and her mother worked such long hours that Eleanora was usually left in the care of her mother’s half-sister, Eva Miller, who herself worked so much that she left young Eleanora in the care of her own mother-in-law. As a girl, she was in and out of a reform school called House of the Good Shepherd. The first time was after she was caught skipping school. The second time was after a neighbor attempted to rape her, and the police needed to keep her somewhere with more protection than her empty home.

She found work as an errand girl in a brothel, and it was there that she first heard the music of Louis Armstrong, the artist she credits as inspiring her to become a performer. In 1929, she moved with her mother to Harlem, where both of them found work in a brothel. Eleanora was thirteen at the time. When the house was raided by police, she was placed in the workhouse on Blackwell’s Island (later renamed Roosevelt Island). When she was released, she decided she’d had enough of being Eleanora Fagan. She sought work as a singer, taking the stage name Billie from her favorite actress, Billie Dove, and the last name Holiday from musician Clarence Holiday, the most likely candidate for being her father. She teamed up with neighbor and aspiring saxophonist Kenneth Hollan and began knocking on club doors. It didn’t take long for managers to realize there was something special about this tragic young kid. She soon had a new home, on the original Swing Street—133rd Street between Seventh and Lenox in Harlem. The Renaissance was in full swing, and Swing Street was its artistic heart.

Something as momentous as the Harlem Renaissance doesn’t have a specific start date. Such large cultural awakenings grow organically over time, and sometimes it’s only in hindsight that we can see a Movement. For the sake of having some starting point, many people cite 1917, the year in which white playwright Ridgely Torrence cast black actors in a series of performances that allowed them to actually be actors—no minstrelry, no blackface. In 1919, poet Claude McKay wrote the poem “If We Must Die,” a piece that served as a clarion call for black Americans to stand up and defy the racism and subjugation that had been their lot in life for so long.

It all happened to the wild sound of a new piano style called Harlem Stride. Jazz, previously regarded as low-class and “Southern,” not really the stuff for more sophisticated urbanites, began to gain popular acceptance among Harlem’s more progressive residents. New clubs opened to showcase the new sound. During Prohibition, many of the Harlem jazz clubs—Tillie’s Chicken Shack, Pod’s and Jerry’s, the Rhythm Club, the LGBTQ-friendly Harry Hansberry’s Clam House—continued on as speakeasies. White patrons who fancied themselves adventurous began making the trip up to Harlem to see this once-in-a-lifetime gathering of musicians that included artists such as Louis Armstrong, Duke Ellington, and Fats Waller. The influx of white patrons was a mixed blessing. It was good because it exposed whites to black culture—not just the music, but also to social and political thinking. It was good because it resulted in integrated streets. But it was bad because those streets sometimes integrated at the expense of black locals, who found themselves pushed out of their own neighborhood by newcomers. And it was bad because some of the clubs, including the famous Cotton Club, opened specifically to showcase black talent for white-only audiences.

King and Queen: Louis Armstrong and Billie Holiday

It was in this dynamic, tumultuous time and place that Holiday took the stage. Her reputation grew quickly. In 1933 producer John Hammond heard her sing for the first time and, that same year, arranged for her first recording, backed by Benny Goodman. Her first recording resulted in her first hit, “Riffin’ the Scotch.”
Hammond had never heard anyone sing like Billie Holiday. There was something about Billie’s voice, something unique. Something to do with smoke and shadow and sex. Something that seems melancholy even when the lyrics and melody are happy. Something a little slurred, a little muddled. Something that could stun you into silence. Exactly the voice you need late at night. Exactly the voice to define a new America. Hammond paired her with an impressive array of musicians, both black and white, including Teddy Wilson, Artie Shaw, and Count Basie, who was at the time in a musical duel with Chick Webb, whose lead vocalist was Ella Fitzgerald. Holiday’s working relationship with Basie was tense. He said she was temperamental, unprofessional, difficult. She claimed he was cheap, and that he demanded artistic changes that undermined the very reason people were coming to see her. The differences between Basie and Billie proved irreconcilable. After a short time together, she left the band.

By the end of the 1930s, Harlem’s Swing Street was gone. The Depression, the end of Prohibition, the rise of organized crime, and the brutal suppression of demonstrations that became the Harlem Riot of 1935 kept patrons away. By then, Billie Holiday was a star who transcended any neighborhood. Hammond booked her at a new place, downtown in New York’s bohemian Greenwich Village, called Café Society. It was opened in 1938 by New Jersey shoe salesman Barney Josephson. From the get-go he intended it as a thumb to the nose of high-falutin’ society. The name was chosen as a joke, a satirical reference to writer and socialite Clare Boothe Luce’s praise of sophisticated “café society.” Josephson referred to his club as “the wrong place for the Right people” — the word “Right” being specifically capitalized as a reference to the conservatives he thought throttled American culture.

Most notable, however, was that it was a racially-integrated nightclub, one of the first in the city. Nightclubs in New York, and indeed across America, had a long history of booking black talent but only allowing white clientele. Josephson’s club welcomed black as well as white patrons, treating both equally. The list of performers who worked the stage at Café Society is staggering. Billie was one of their star performers, and also one of their most daring. There was a night in 1939 when she took the stage and delivered her usual wonderful set…until she got to the last song, one she hadn’t performed before. Audience members were thrown for a loop. Wait service stopped. They shut off all the lights but one, a spotlight on Billie’s face, her eyes closed. In that silent darkness, Lady Day launched into the song, “Strange Fruit.”

The song was originally written as a poem by teacher Abel Meeropol, who was moved to pen it after seeing a photo taken by Lawrence Beitler in 1930 depicting the lynching of two black men, Thomas Shipp and Abram Smith. Meeropol searched unsuccessfully for a partner who could set the poem to music. Eventually, he did it himself, performing “Strange Fruit” with vocalist Laura Duncan. Someone at Café Society, either Josephson or director Robert Gordon, heard it and convinced Holiday to perform the song at the club.
At first, she was wary. It is a chilling song, subverting the image of trees laden with fruit by likening it to hanged black men. Holiday was nervous about reprisals, but Josephson convinced her to go through with it. The audience was awestruck. It was so well received that it became a regular part of her Café Society shows. When it came to recording it, however, producers were as wary as Holiday had first been. After Columbia, the label to which Holiday was signed, refused to let her record the song, she turned to producer John Hammond, who also balked. Holiday then took the song to Milt Gabler’s small, avant-garde Commodore label. It was there she was finally able to record “Strange Fruit.”

Café Society continued challenging the establishment, breaking down barriers, and fostering incredible musical talent, until the club came under intense harassment from the House Un-American Activities Committee, that Congressional mob charged, in theory, with ferreting out Communist threats at the expense of any sense of free speech or Constitutional rights. After Barney Josephson’s brother, Leon, was called to testify before the committee and refused, a propaganda campaign was waged against Café Society. In 1947, Barney had no alternative but to close it down, another victim of the Red Scare plaguing the country.

Social upheaval and the end of Prohibition may have shuttered many of the famous nightclubs on 133rd Street, but jazz proved it could adapt and survive. It found a new home in the cafés and nightclubs of Greenwich Village, and it found a new Swing Street on 52nd between Fifth and Seventh Avenue. Clubs such as 3 Deuces, The Onyx, and Club Carousel kept the Harlem Renaissance alive, even if it wasn’t in Harlem anymore (the biggest club in Harlem at that time was Minton’s, popular because the owner was more than happy to indulge musicians with free food and drink).

The pioneers of the ’20s and ’30s turned these new stages over to the new generation of jazz legends: Charlie Parker, Thelonious Monk, John Coltrane, Miles Davis. Big band and swing gave way to bebop, and bebop to cool jazz and hard bop. But Lady Day remained. In 1939, Frank Sinatra—born the same year as Holiday—saw her at the Uptown House. He was entranced (and probably smitten). “Standing under a spotlight in a 52nd Street jazz spot,” he recalled, “I was dazzled by her soft, breathtaking beauty.”

Sinatra undoubtedly learned lessons from Holiday, like how to use emotion and how to turn a song into a story. He later said of Billie, “It is Billie Holiday who was, and still remains, the greatest single musical influence on me.” Throughout the 1940s, her popularity continued to grow. Her best known and biggest hits, songs like “God Bless the Child” and “Lover Man,” were from this era. She well and truly was the voice of America, and it seemed there was really no stopping her. Then, in 1947, it all started to fall apart.

Though an open secret among the people with whom she worked, Holiday’s addiction to heroin became public knowledge when she was arrested in 1947. Many who owed their success to her abandoned Billie during this setback. When her lawyer no-showed the trial, she plead guilty and was sent to Alderson Federal Prison Camp, better known as Camp Cupcake (later the temporary residence of Martha Stewart). She was released less than a year later and, despite having no albums released in years, performed to a sold-out house at Carnegie Hall. A successful follow-up show on Broadway in 1948 seemed to signal that, despite addiction, legal setbacks, and the march of time, Lady Day was still a force to be reckoned with.

But in 1949, she was arrested once again on possession charges, this time in San Francisco. Although she recorded another of her most famous songs, “Crazy He Calls Me,” in the wake of this second arrest, her popularity took a hit. She began to disappear from American radio. New York used her drug arrests to justify revoking her Cabaret Card. Implemented in 1940, the New York City Cabaret Card system required artists be licensed to perform in any establishment that served alcohol. The law was repealed in 1967, thanks largely to Frank Sinatra’s threat to never perform in New York again, but for Holiday in 1949, it meant she was effectively banned from just about every club in the city. At least she was in good company—over the years, Charlie Parker, Chet Baker, Thelonious Monk, and Lenny Bruce had their cards revoked as well.

Loss of the card forced Billie into smaller venues for less pay. Critics said her voice was shot, that it was all over, but she soldiered on. In the 1950s, she toured Europe and began recording for the Verve label, releasing albums that proved audiences still wanted her music, and that reports of the demise of her voice were greatly exaggerated. In 1956, in support of the release of her suspect autobiography, she recorded “Lady Sings the Blues,” the song that would become synonymous with Billie Holiday. She returned triumphantly to Carnegie Hall that same year. In 1957 she married a hustler named Louis McKay, a small-fry goon who, liked most of the men Billie ended up with, treated her poorly. But he was committed to getting her off heroin, even if it was not for altruistic reasons. He lived better when she was performing well, and he planned to franchise her name to open a chain of Billie Holiday recording studios.

In 1958, she once again proved the critics who were writing her off wrong, recording Lady in Satin, one of the greatest albums of her career. She toured Europe again in 1959 and began recording an album for MGM. It was released posthumously. Billie Holiday died on July 17, 1959, at the age of 44.

Swing Street didn’t survive, either. The Cotton Club, 3 Deuces, Onyx—all gone. Most of the Greenwich Village clubs are gone as well. No plaque commemorates Café Society, though a block away is another historic joint, the Stonewall Inn. But despite the changes, despite all that has come and gone, despite the fact that New York has torn down and rebuilt itself a dozen times since she first set foot on a Swing Street stage, Billie’s voice remains. You can still bow your head at the bar, feel the chills as you let Billie’s voice wash over you, and take one last drink before you bid goodbye to the bartender and head out into the night.
You don’t want to wish woe on anyone, but when tragedy forges a talent like Billie Holiday, you can tell yourself at least some of it was worth it. Like Sinatra said, “Lady Day is unquestionably the most important influence on American popular music in the last 20 years. With a few exceptions, every major pop singer in the United States during her generation has been touched in some way by her genius.”

Inside the 21 Club

The Start of Something Big

While Sidney Falco was pushing through the drunks at Toots Shor’s, J.J. Hunsecker was presiding over a more refined­—but no less frenzied—scene a short distance away at the 21 Club, which, despite the changes in the city over the years, remains a stalwart presence on the block that used to swing but now mostly manages investments and whatever else it is bankers do in those austere, anonymous skyscrapers. Located at 21 West 52nd Street and opened (as a speakeasy, naturally) during a wild party on Dec. 31, 1929, it’s one of the city’s few remaining establishments that expects you to dress up. Jeans are forbidden, and a jacket is required (sadly, they relaxed the rule about ties in 2009).

Before settling in at the address that would stay theirs for decades, 21 bounced from location to location. In 1922, cousins Jack Kreindler and Charlie Berns opened the first incarnation, known as the Red Head, in Greenwich Village. They later moved to Washington Place and changed the name to Fronton, then moved again to 42nd St., where it was known as the Puncheon Club. It was at this location they introduced the more elegant atmosphere, which stayed in place when they moved to 52nd St. and christened the new location Jack and Charlie’s ’21’.

“A more elegant atmosphere” doesn’t mean a reserved atmosphere. This was still Prohibition after all, and what went on at 21 was still illegal. Like many speakeasy proprietors, Jack, Charlie, and their staff devised a number of ingenious contraptions to help them avoid getting busted during raids. There was a lever near the bar which, when thrown, would tilt the shelves so the booze dropped down a chute into the city sewer. The bar itself could rotate into a hiding place behind the wall. There was also a secret door leading to the club’s wine cellar.

When J.J. Hunsecker used it as his office away from the office in Sweet Smell of Success, 21 was a hive of activity. This was the age of two, three, four martini lunches and lots of business in the dining room. Each table had a phone jack nearby. Writers, advertising executives, and celebrities would stay for hours with assistants running in and out all day. It wasn’t a quiet, romantic night out, but if you were making the scene, or like J.J., breaking someone’s scene, 21 was where you staked your territory. “Still the snappiest restaurant in New York,” wrote Spy magazine in 1960, in a description of the place that perfectly captures its appearance in Sweet Smell of Success. “A caste system operates in this plush spot, separating the big from the small and the biggest from them all.”

Sydney and JJ at 21 in Sweet Smell of Success

Sidney Falco is one of the small, looking to sit at the biggest table. J.J.’s table. Ostensibly, it’s because Falco wants his latest client to succeed, and a kind mention from J.J. would cement that. As the film progresses, it becomes less about client success and more about Sidney’s obsessive drive to make it, for himself to succeed. J.J., recognizes that whiff of desperate fear, like any well-honed predator would. He is more than happy to dangle the bait in front of Sidney and offer him a deal. It might destroy a couple lives, and it would definitely blacken Sidney’s soul, but hey…what’s that compared to the sweet smell of success?

Toots Shor’s was a place for a whiskey sour and a plate of indifferent grub. Jilly’s slung cheap Chinese food. 21 was where you went for a good meal. They prided themselves on their food and have worked for some 85 years to maintain that reputation. Similarly, they’ve sought to keep pace with the changing face of cocktail culture, from the classics like Manhattans and Martinis that would have been the lifeblood of Hunsecker to the craft cocktails that define the landscape today. But people still expect a certain level of old-school tradition from 21, so they’re not going to stray far from the classics. You won’t find dry ice and mystery pearls in their cocktails. And if there’s one cocktail, besides the Martini and Manhattan, that characterizes the 21 from the era of Sweet Smell of Success, it’s the Southside.

Today, the atmosphere at 21 has calmed down a little, and alas, the table-side phone jacks are gone, but it’s still a place to see and be seen, as well as the site of countless business deals. World leaders, artists and actors, and business moguls can still be seen there any day of the week. In its long history, the restaurant has played host to writers, movie stars, singers, average folks looking for a fancy experience to remember, and every American President since Franklin Roosevelt, except for George W. Bush. You will also find local New Yorkers and visitors who have come to experience the history. While people can wait months to get a reservation at whatever the new trendy restaurant might be, it’s easier to secure a table at a classic like 21.
The Club was even dragged into a brouhaha when President-elect Donald Trump ditched the press corps and sneaked out for a private meal. His destination? 21 Club, where so many other presidents and dignitaries and dukes and duchesses have enjoyed a meal beneath the dining room’s ceiling of knick knacks, including a model PT boat donated by John Kennedy.

“Prohibition raids, Hemingway escapades, Marilyn Monroe and Joe DiMaggio, a gift from JFK,” says Avery Fletcher, current Director of Sales and Marketing for 21. “Jackie Gleason swapping a model train for the pool cue from The Hustler, Gordon Gecko (Michael Douglas) declaring ‘Lunch is for wimps’ in Wall Street, Nelson Mandela, Bette Midler, Jimmy Fallon crossing the room to offer Wes Anderson a taste of his Chicken Hash.”
It’s hard to think of a place where so many disparate temperaments, political alignments, and types of people have gathered peacefully, entering the street-side iron gates flanked by a retinue of ever-vigilant jockeys. As, one by one, the famous clubs of Swing Street began to die off, 21 weathered the storm, thanks perhaps to the fact that they proved a little more competent in managing their money than neighbors like Toots Shor and Jilly Rizzo, both of whom it seemed could never stay out of debt or off the IRS’ radar. The food was also better. Even as skyscrapers sprouted up around them, replacing the old establishments, 21 remained, as Fletcher describes it, “the lone reminder of Swing Street’s previous self; standing tall figuratively though dwarfed physically.”

Match Me, Sidney

By the time Sweet Smell of Success hits its closing shot, as the mournful menace of the Chico Hamilton Quintet’s “Night Beat” signals a ceasefire to the evening’s battles, the viewer, like the characters, has been through the ringer. No one emerges unscathed. Lives are ruined, perhaps more and different lives than J.J. Hunsecker hoped…including his own. There is a sense of exhaustion, carnage, defeat. Not everyone survives a night in New York. Not everyone returns in the morning.

But other lives go on. Other people have found the inspiration, however ugly the source, to be reborn, to pick themselves up and strike out in search of something new. As the sun rises on the streets of New York, littered with the casualties of another night of revelry, deal-making, and sin, the grime and filth seems somehow…admirable? Maybe. A red badge of courage? Perhaps.

And those who didn’t survive the night? Maybe they’ll be remembered. Maybe not. Maybe someone will eulogize on their behalf…if they can remember the names. If there’s even time to bother. After all, it all starts again the next evening. Some will return for another go-round. Others will be taking the field for the first time. That’s the game. That’s the city. It’s not going to pause for you to catch your breath and lick your wounds. This city doesn’t have time to stand still, and why would anyone want to live in a New York that stands still?

Even if Toots Shor’s is gone, even if Swing Street is gone, even if 21 Club is the lone guardian of that wild, damaged, enthralling Swing Street era, it’s hard, if you really have the city in your blood, not to stand there surrounded by all the concrete and glass and human wreckage and say to yourself, like J.J. Hunsecker, “I love this dirty town.” §

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