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New York is birthplace and ground zero for some of the world’s most popular things to eat and drink including chicken and waffles, egg creams, Eggs Benedict, Waldorf salad, NYC-style pizza, Nathan’s hot dogs, Baked Alaska, and Dominique Ansel’s people-still-line-up-for-it-every-morning cronut. The same goes for some of the world’s most iconic cocktails, so why not tipple your way through history with these five classic libations, which you can enjoy at their birthplaces (in some cases) or superior downtown spots like Waverley Inn, Pouring Ribbons, PDT, and Paul’s Cocktail Lounge.

The Old Fashioned

NYC Birthplace: The Waldorf-Astoria Bar

The Old Fashioned we know today may have its roots in Louisville, Kentucky, where bartender James E. Pepper first devised the recipe at The Pendennis Club circa the late 1800s, but the cocktail only truly rose to fame when Pepper introduced the concoction at New York City’s Waldorf-Astoria (that recipe can be found in The Waldorf Astoria Bar Book). Famously Don Draper’s libation of choice and still riding high on Mad Men’s pop culture tail, this combination of muddled sugar, Angostura bitters, soda, and either whiskey, Scotch, brandy, bourbon, or rye is sometimes accompanied by orange or citrus rind. “We muddle a slice of orange and also put a slice of orange on the side,” says Roger Jazilek, a longtime veteran of the New York bar and restaurant scene who can be found these days working his magic at Paul’s Cocktail Lounge (pictured above, front and center).

The Manhattan 

NYC Birthplace: The Manhattan Club

Another 19th-century invention (circa the 1870s) that bears similarity to the Old Fashioned—sweet Vermouth instead of muddled sugar is the main difference. The Manhattan, it is said, was first whipped up Manhattan Club, a now-defunct social club, for a banquet honoring New York City Governor Samuel Tilden when he was a candidate for US President. “When you come to Manhattan, you should always have a Manhattan,” Jazilek insists. Although the recipe remains essentially the same as when it was first imbibed, some mixologists give the tiniest twist to its components. “It calls for red Vermouth, but at Paul’s, we use Antica Vermouth which is more spicy and interesting, and instead of a cherry we use brandied cherries so it’s a more exciting Manhattan than the usual.”

The Bloody Mary, aka The Red Snapper

NYC Birthplace: King Cole Bar at St. Regis Hotel

Ubiquitous at brunch, The Bloody Mary—vodka, tomato juice, salt, pepper, and Worcestershire sauce—was the handiwork of a French bartender named Fernand Petiot who essentially spruced up a 50/50 vodka-tomato juice combination favored by comedian of the day George Jessel, in 1934. You can still savor Petiot’s recipe replete with a lemon wedge and Spanish queen olives at the King Cole Bar today (they served the one millionth in 2017), although “the glassware is certainly different,” says Will Rentschler, St. Regis’s director of food and beverage. Rentschler also notes that “Red Snapper” isn’t a gin variant and that the name was simply used because Bloody Mary was considered too vulgar during the time of the cocktail’s invention. “It’s a very personal drink,” he says. “Guests are very particular how they take it: some with olives, some without, some very mild, others with a lot of spice and kick. Everybody has a certain way they like it and can’t be convinced otherwise, and it’s a very simple drink in itself, which lends itself to the creativity of the person making it.”

Moscow Mule

NYC Birthplace: The Chatham Hotel

Traditionally served in a copper mug, this frosty blend of vodka, ginger beer and lime reportedly dates back to 1941, when three pals, including the heads of Smirnoff Vodka and Hollywood California’s Cock ’n Bull Tavern (which fashioned a ginger beer), had the brainstorm of combining their respective products with lime juice for good measure. Upon returning to the West Coast, the drink was officially launched in the Tavern. In honor of its still proliferating fame and popularity (and variations), March 3rd, 2017 marked the first annual National Moscow Mule Day, and you’ll find no shortage of recommended spots to try classic and nouveau takes. “We don’t really make the classic Mule because it has ginger beer,” Jazilek notes. “We make the ginger syrup ourselves and mix that with soda so it’s more interesting.”

The Cosmopolitan

NYC Birthplace: The Odeon

Tribeca’s The Odeon can be lauded—or chastised—for birthing the pink-toned, quintessentially Sex And The City accessory that dates back to 1987. Absolut Citron vodka, Cointreau, cranberry juice and fresh lime juice shaken and poured into a martini glass, it’s “the cocktail that wouldn’t die,” Jazilek jokes. “It was big in the ’80s before Sex And The City and used Absolut Citron for a lemony flavor. Absolut was the biggest-selling vodka at the time with fantastic advertising. Maybe once in a blue moon, someone orders an Appletini, but Cosmos once or twice a week maybe.”

Words Lawrence Ferber

Photography courtesy of Paul’s Cocktail Lounge

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