Vermouth had just hit the States, and mixing the classy new European import with whiskey was a brilliant marketing move to make it less intimidating and foreign to American drinkers. By the 1880s the Manhattan had been featured in Esquire, classic cocktail recipe books and become part of the city’s identity. A fixture on the cocktail menu at top New York bars like Delmonico’s, WaldorfAstoria, and Hoffman House, mixing a Manhattan was now considered a test of a bartender’s skill, thanks to its short ingredient list and emphasis on technique. It was conventionally thought of as a man’s drink, but also enjoyed by intellectual women in more progressive social circles. Once it hit the menus in train bar cars from New York to Chicago, the drink of choice for businessmen riding firstclass, the cocktail transcended its birth city and went nationwide.

The start of Prohibition put the kibosh on the production of American rye whiskey, but not on the growing popularity of the Manhattan. Bartenders at underground speakeasies used anything they could get their hands on to make this trendy cocktail: bootleg spirits, housemade bitters and cheap vermouth. To compensate for the inferior ingredients, they’d load it up with sugar, absinthe rinses and lots of ice, depending on the region and what was available to them. This spirit of improvisation established the Manhattan as a symbol of adaptation and rebellion, cool jazz and smoky glamour. Bartenders also swapped in more accessible bourbon or Canadian whiskey, a mellower counterpart to domestic whiskey that resulted in smoother cocktails with far less bite changes to the flavor profile that still echo in the Manhattan of today.

When Prohibition was finally repealed in 1933, distilleries reopened and US whiskey came flowing back into American lives as if it had never left. The Manhattan assumed its ubiquitous presence in cosmopolitan drinking culture, often served as a predinner drink at fine hotels and restaurants. Along with the Old Fashioned and the Whiskey Sour, the Manhattan became known as one of the three kings of whiskey cocktails, each cocktail a radically different showcase of the spirit’s versatility.

But as the cocktail hour found its way into the average family home postWorld War II around the midcentury, drinkers’ tastes and cocktail culture in general began to change from work mode to play mode. Women, younger drinkers, and other demographics historically left out of cocktail culture until it became more integrated into domestic life were turned off by the masculine, serious connotations of cocktails like the Manhattan, and craved lighter, sweeter, simpler drinks. The Manhattan began felt stiff and overly formal, a holdover from an earlier era that men in their 50s enjoyed at business lunches. This was also thanks in large part to the new, aggressive marketing of vodka, fostering the public’s interest in screwdrivers, Cosmopolitans and vodka martini variations.

Initially, it was modified to suit the new tastes: made sweeter with bourbon and a bright red cherry garnish, casually shaken instead of carefully stirred, served over ice rather than up, and featuring basic domestic vermouth rather than a true imported bottle with a more complex herbal profile. Folks coming home tired at the end of a long workday relied on shortcuts like processed mixers and artificial flavors to mix up a quick, tasty cocktail and unwind. All this added up to a marked decline in cocktail quality that some purists call a dark age of drinking culture. Eventually, like many classic cocktails, the Manhattan was mostly phased out for lighter, more modernfeeling options, and remained mostly dormant through the end of the 1980s.

But if there’s one thing about cocktail culture that you can rely on, it’s that everything old will someday be new again. For the Manhattan, that day arrived in the late 1990s, when pop culture experienced a resurgence of interest in the retro aesthetic of the 1940s. (See also: what’s happening right now with the 90s). Along with movies like Swingers, the heritage cocktails of preProhibition came roaring back in style, along with a renewed appreciation for the crafts and techniques that made these drinks so special in the first place.

New York was the epicenter of the new foodie culture, and bartending as profession had just begun its professional glowup. Bartenders at highend speakeasies dusted off the Manhattan and polished it back to a high shine using quality vermouth, housemade bitters, chilled glassware, a thoughtful garnish, and the triumphant return of rye whiskey as a base. By the 2010s, the Manhattan had become cool again in major cities across the country, a pop culture favorite it’s Don Draper’s drink of choice and a template for endless innovation. There’s the Black Manhattan, which swaps amaro for sweet vermouth; the barrelaged Manhattan; the smoked Manhattan, and seasonal riffs featuring Applejack, mezcal, cherry bark bitters and more. From trendy to timeless, the Manhattan is here to stay.