Bar History: I Love This Dirty Town (Part 2)

A historic peek into ’21’ Club from the lens of Sweet Smell of Success

21 Club - Exterior SunsetPart One discussing character Sidney Falco’s favorite haunt, Toots Shor’s, can be read here.

All photos courtesy ’21’ Club

The King of 52nd Street

While Sidney was pushing through the drunks at Toots Shor’s to the sound of the Chico Hamilton Quintet playing in the corner, JJ was presiding over a more refined but no less frenzied scene a short distance away at the ’21’ Club (previously featured here), which despite the changes in the city and that block in particular 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 (though 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. Originally, it was located in Greenwich Village as far back as 1922, when cousins Jack Kreindler and Charlie Berns opened the first incarnation, known as the Red Head. They later moved to Washington Place  and changed the name to Fronton, and then moved again to 42nd St., where it was known as the Puncheon Club. It was this version that saw the introduction of a more elegant atmosphere, which stayed in place when they finally moved to 52nd St and christened the new location Jack and Charlie’s ’21’.

21 Club - Archive 10“A more elegant atmosphere” doesn’t mean a chaste 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 quickly and efficiently tilt the shelves so that all the booze dropped down a chute and into the city sewer while the bar itself smoothly rotated to a hiding place behind the wall. There was also a secret door that led to the club’s secret wine cellar. After Prohibition, the sophisticated air and clientele the cousins had cultivated during their illicit years stayed loyal. And, remarkably, they’ve remained loyal ever since.

When JJ Hunsecker used it as his office away from the office in Sweet Smell of Success, ’21’ was a hive of activity. “Though none of our associates date back quite that far, we have learned over the years that the buzz in Sweet Smell of Success is an accurate portrayal of the time,” says Avery Fletcher, ‘current Director of Sales and Marketing for ’21’. “This was an age of 2, 3, 4 Martini lunches and lots of business in the dining room. Each table had a phone jack nearby and writers, advertising executives, and celebrities would stay for hours with assistants running in and out all day long.” It wasn’t a quiet, romantic night out, but if you were making the scene, or like JJ 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.” 4

Gene Autry visits '21' in the 1950s
Gene Autry visits ’21’ in the 1950s

Sidney Falco is one of those kids looking to sit at the big table, at JJ’s table. Ostensibly, it’s because Falco wants his latest client to succeed, and a kind mention from JJ would pretty much cement that. But as the film progresses, it becomes a lot less about the client succeeded and more about Sidney’s obsessive drive to make it, for he himself to succeed. JJ, recognizing that whiff of desperate fear like any well-honed predator would, is more than happy to dangle the bait for Sidney and offer him a Faustian 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? If one wants to scour away some of the romanticization of the Mad Men era, which wasn’t exactly as great a time for many as it was for white guys, Sweet Smell of Success goes a long way to poking that seedy underbelly and skewering “dog eat dog” machismo.

Toots Shor’s was a place for a beer and a whiskey and a plate of grub, and nearby Jilly’s slung cheap, hearty Chinese food, but ’21’ was where you went for an actual 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 mid-century classics like Manhattans and Martinis that would have been the lifeblood of Hunsecker and his crew to the book in craft cocktails that defines the landscape today.

“We aim to blend the classic with the contemporary for our cocktail selections,” says Avery Fletcher. “Seasonal creations like the Iron Gate Old Fashioned, Jam Mule and Secret Password feature housemade gastriques, syrups and bitters.” Though, she adds, people today expect a certain level of old-school tradition from ’21’, so they’re not going to stray too far from the classics. “You won’t find dry ice and mystery pearls in our cocktails.”

the Bar Room at '21' as it is today
the Bar Room at ’21’ as it is today

She says if there’s one cocktail, besides the aforementioned Martini and Manhattan, that characterizes the ’21’ Club of Sweet Smell of Success’ era, it’s the Southside:


  • 2 oz Plymouth gin
  • 1 oz fresh lemon juice
  • 5  mint leaves
  • 1 oz simple syrup

In a shaker, muddle the mint and lemon juice. Add the remaining ingredients, fill with ice, and then shake and strain into a chilled Martini glass. Garnish with a mint sprig or lemon twist.

Similarly, the atmosphere at ’21’ Club has calmed down a little, and alas, the table side phone jacks are gone. “The technology has changed with cell phones replacing the table side plug-ins and perhaps the pace is a little less frenetic,” says Fletcher, “but ’21’ today is still a place to see and be seen as well as the site of many business deals. World leaders, artists and actors, and business moguls can still be seen here any day of the week. Of course, today, you will also find local New Yorkers and visitors who have come to experience the storied history.” Which is true. While people wait months and years to get a reservation at whatever the new trendy restaurant might be, it’s easier to secure a table at a classic like ’21’. When I had dinner there, I didn’t spy any titans of modern culture (to be fair, I would recognize more people from 1957 than 2017), but I did bond with an older gentleman who was initiating his college-age grandson into the family tradition of enjoying a meal at ’21’. Also, he was explaining to the younger generation the importance of the dress code and why it’s nice to have some places that still enforce standards of attire.

Richard Nixon visits '21'
Richard Nixon visits ’21’

In its long history, 21 has played host to writers, movie stars, singers, and every American President since Franklin Delano Roosevelt except for George W. Bush. In fact, the club was recently dragged into a brouhaha when newly minted President-elect Donald Trump ditched the press corp and snuck out (or at least tried to) 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 iconic ceiling of knick knacks and ephemera, including a model PT boat from JFK. “Prohibition raids, Hemingway escapades, Marilyn Monroe and Joe DiMaggio, a gift from JFK,” reflects Fletcher, “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 all passed through the street side iron gates flanked by a retinue of ever-attentive 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 had, say, neighbors like Toots Shor and Jilly Rizzo, both of whom could never seem to stay out of debt or off the IRS shit list. The food was also much better at ’21’. Fletcher adds, “Our core tenants of fine cuisine, wine and service in a sophisticated fun environment will never change. However, we do continually adapt to the evolving wants and needs of our guests. Whether it is integrating contemporary mixology or culinary techniques into our menus or being one of the first luxury restaurants in NYC to have a Facebook page.” Even as skyscrapers sprouted up around them, replacing the old establishments, ’21’ remains “the lone reminder of Swing Street’s previous self; standing tall figuratively though dwarfed physically.”

21 Club - Exterior with Doorman 2By 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 have been through a ringer, and no one emerges unscathed. Lives are ruined, perhaps more and different lives than JJ Hunsecker hoped. But lives have also found the inspiration, however ugly the source, to be reborn, to peel themselves away from the pack 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 still seems somehow…admirable? Maybe not? A red badge of courage? Perhaps. And whoever didn’t survive the night? Maybe they’ll be remembered. Maybe not. Because it all starts again later that evening, some players returning, others taking the field for the first time. That’s the game. Who wants to live in a New York that stands still? And even if Toots Shor’s is gone, even if Swing Street is gone, even if ’21’ Club is one of the lone remaining guardians 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 JJ Hunsecker, “I love this dirty town.”


  1. (from part one) Bowery Boys (2015, January 13). Toots Shor’s and the art of celebrity male bonding. Retrieved July 13, 2017, from
  2. (from part one) Jeremiah’s Vanishing New York ( (2011, January 24). Leon and Eddie’s. Retrieved July 13, 2017, from
  3. (from part one) Caiafa, F. (2016). The Waldorf Astoria bar book. NY, NY: Penguin Books, an imprint of Penguin Random House, LLC. pp. 330-331
  4. Kriendler, H. Peter., and H. Paul Jeffers. “21”: Every Day Was New Year’s Eve: Memoirs of a Saloon Keeper. Dallas, TX: Taylor Pub., 1999. Print.

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