With its three-pillar construction—base spirit, sugar and citrus—the simple sour template provides the blueprint for countless classic cocktails, from the Margarita to the Daiquiri. But within this category, it’s the Whiskey Sour that has occupied a position of unparalleled popularity in the history of American drinking for more than a century and continues to inspire modern interpretations today.

The first printed record of the Whiskey Sour appears in 1862 in Jerry Thomas’ How to Mix Drinks, though the recipe likely dates back many years earlier. Relying on sugar to be dissolved in a small amount of water before adding the remaining ingredients, rather than syrup, the original Whiskey Sour construction resembles that of punch. But unlike punch, the Whiskey Sour has always been made on a small plan, a fact that makes it difficult to pinpoint the drink’s precise origins.

By 1870, however, its popularity was well enough established that it required no explanation when printed in a feature in the Waukesha Plaindealer, a Waukesha, Wisconsin, newspaper. Indeed, as David Wondrich observes in Imbibe!, at the peak of its popularity between the 1860s and the 1960s, the Whiskey Sour “was one of the cardinal points of American drinking, and… one of the few drinks that could come near to slugging it out with the vast tribe of cocktails in terms of day-in, day-out popularity.”

While the original three-ingredient cocktail is still the best-known version, other early renditions of the drink have since gone on to become classics in their own right, from the red wine-topped New York Sour to the frothy Boston Sour, made with egg white—a PUNCH favorite. From there, many of today’s bartenders have contributed simple riffs to the canon. Switching up flavors via the additions of liqueurs and nontraditional sweeteners results in a wide variety of Whiskey Sours, though most of them still hew closely, at least in construction, to the original template.

Here, get to know the Whiskey Sour and its modern interpretations.

Classic: Whiskey Sour
Modern: Midnight StingerMott and MulberryBetty Carter, Penicillin, Ol’ Pepper, Thirsty Monk, Mountain Man

Making a riff on the Whiskey Sour can be as simple as splitting the base, as is the case with the Midnight Stinger from Sam Ross, who splits the base between bourbon and Fernet Branca. (Leo Robitschek similarly splits the base of his Mott and Mulberry between equal parts rye and Luxardo Amaro Abano.) Most commonly, though, bartenders rely on alternative sweeteners to add complexity, like pêche de vigne in the Mountain Man, PX sherry in the Betty Carter, chipotle honey and honey-ginger syrup in the Ol’ Pepper and Penicillin, respectively, and both Bénédectine and génépy in The Thirsty Monk.

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