The Stinger is a native New Yorker. A product of the city’s Gilded Age, it would—if personified—don a top hat and monocle. Though its popularity has ebbed and flowed over the past 130 years, today, as the city’s newest bars look back to its past for inspiration, the Stinger is reemerging as a swanky expression of New York-in-a-glass.

The Stinger’s life began at the southwestern corner of Madison Square Park in 1890. Originally christened the Bartholdi Cocktail after the hotel where it was born, the two-part combination of Cognac and crème de menthe was simply shaken, served up and garnished with a lemon twist. It didn’t take long for the Bartholdi Cocktail to head uptown across Madison Square Park, where it landed seven blocks north at the Holland House Hotel. There, George Kappeler added two dashes of Angostura bitters to the formula and, putting his own spin on it, renamed it the Brant Cocktail. 

Up Fifth Avenue the Brant Cocktail went, finding yet another home in the bar at the Waldorf-Astoria, which also created its own riff on the drink: The Prince, a rye-based version, featured orange bitters in place of Angostura. From the Waldorf, the minty cocktail moved further up Fifth Avenue to West 57th Street and the palatial mansion of Reginald Vanderbilt. He’d shake them up for himself and friends in his barroom, always with a dash of absinthe added. But Vanderbilt didn’t call this drink the Brant or the Bartholdi—he called it the Stinger.

Strangely, the name is the only element associated with the drink’s history that seems to have originated outside of the New York milieu. Perhaps drawn from the world of boxing (referring to a quick jab), the Stinger name was first attached to the drink in a handwritten addendum tucked into William T. Boothby’s American Bartender around 1910, attributed to John C. O’Connor’s bar in San Francisco. Then, in 1913, Jacques Straub included it in the popular bartender manual Drinks.

By the 1940s, the drink—now strictly traveling under the Stinger name—was still enjoying immense popularity. It appeared on the 1944 cocktail list at Brooklyn’s Gage & Tollner; no surprise, as the venerable chophouse was, by that time, already seen as a Gay ’90s time warp. Given its lineage, the Stinger is understandably undergoing something of a renaissance in present-day New York’s new—or newly revived—opulent restaurants.

In 2021, while preparing to reopen the bar at Gage & Tollner (which had sat dormant for over 15 years), co-owner St. John Frizell methodically worked through every drink on the restaurant’s WWII-era cocktail list and, in collaboration with Jelani Johnson, developed the Stinger that now graces the menu there. The pair worked off of the Kingston Stinger, a rum-based version that Zac Overman had developed at Frizell’s Red Hook bar, Fort Defiance. The resulting recipe combines Cognac, white crème de menthe, Branca Menta, rich Demerara syrup and fresh mint, all shaken and strained into a snifter over pebble ice then served with a bouquet of mint and a Jamaican rum float. For Frizell, the charm of the Stinger is that it’s a quintessential New York nightcap, what he calls an “out-on-the-town cocktail.”  

Just as the city is experiencing a resurgence of the chophouse, the restaurant scene at Rockefeller Center—one of the most “New York” of New York places—has also been undergoing a transformation. Nowhere is this clearer than at Le Rock, a stunning restaurant that channels the New York–French cuisine that enjoyed a spate of popularity during the postwar years. In addition to a list of Martinis and original house cocktails, beverage director Estelle Bossy serves a Stinger frappé over pebble ice as an after-dinner cocktail in a nod to the midcentury period, when the drink first started getting the crushed ice treatment. 

Le Rock’s Stinger employs the same batch-and-freeze method used for the house Martini program, which Bossy says makes for a perfectly viscous drink. Instead of Cognac, she reaches for a more freezer-friendly five-year-old Armagnac, which “brings an oily, beefy meatiness that flavors cling to,” she explains. Not only does the drink fit right into Bossy’s Francophile program, it offers a showcase for crème de menthe to redeem its lowbrow reputation. “Everybody’s scared of crème de menthe, right? I mean, people still trash the Grasshopper, [but] it’s so yummy,” Bossy says. As Frank Caiafa, former bar manager at the Waldorf-Astoria, notes, the liqueur was a staple in the 1970s, too—another era that has been the subject of a host of modern-day bar concepts and spinoffs. “Everyone had crème de menthe in the house and you drank it,” he says. “It landed on the Sunday dinner table, along with anisette and Galliano.”

Bossy’s is an approach that mirrors the Stinger that William Elliott used to serve at the bygone Sauvage, a stylish Brooklyn brasserie that made for a natural home for a drink built on two French ingredients. Like Bossy’s version, his was batched and frozen, though he doctored the drink with a dash of absinthe à la Reggie Vanderbilt, and served it up in a coupe over a hand-carved hunk of ice. 

Between hotel bars, steakhouses and ’70s throwbacks, New Yorkers are nostalgic for the city’s earlier eras. The casual style of service that rose to prominence 20 years ago is giving way to more formal spaces, and cocktails from days gone by—the Martini chief among them—have become wildly popular once again. In this new (old) New York, could the Stinger be the next big thing?