We all have that one drink: the cocktail standard that we order when we’re feeling fancy, and we want a little more than Blank & Blank. I’m talking about the go-to when you’re dressed up for the night, and you want to feel like your drink made as much effort as you did to be standing in this bar wearing your new bomb-ass boots. For me, that cocktail is the Old Fashioned. And if I want to class up my personal joint (and I am assured that the bartender has time), I order what I consider to be the most classic of bourbon cocktails.
If it’s not the most classic, it is probably the oldest, or at least the oldest to be given the name “cocktail.” The term cocktail can be traced as far back as 1806, and in the strictest version of the the term it means a drink that is composed of any spirit, sugar, water, and bitters…so if you know the recipe, you can see how the Old Fashioned would be one of the oldest. But in case you don’t know, this is the Scout (and generally) accepted recipe:
Put some sugar (1 cube, a bar spoon full, or some simple) at the bottom of the glass, add two healthy dashes of bitters, and stir or muddle, depending on your sugar type. Add a couple ice cubes and a healthy serving of bourbon (rye is acceptable if bourbon for some reason is unavailable). Stir to combine. Finish with the essence of an orange peel (twist it above the glass to release all those good oils and rub it around the rim) and garnish with said orange peel.
Note: Some people will tell you there should be a cherry in there; those people, in my personal opinion, are wrong. God forbid someone muddles said cherry, and bless their hearts if it was a maraschino. Now I realize I may not be in the majority here; said people include the apparent namers of the cocktail, and a certain hometown establishment for Zelda and me, The Pendennis Club (Maybe if they let more women in, they’d get it right…but I digress. More on them later.). You do you, I guess: Just keep all cherries away from my old fashioned’s, please.
The name “Old Fashioned” probably initially referred to all drinks made in this spirit-sugar-water-bitters style. The term came into prominence in the late nineteenth century and referred mostly to drinks made in “an old fashioned style,” as opposed to with newfangled liqueurs and the like. There were old fashioned cocktails made with gin and whiskey and brandy (see: a gin version mentioned in 1862’s Jerry Thomas’s Bartender’s Guide: How to Mix Drinks). But the whiskey and bourbon versions gained more and more popularity as the nineteenth century turned into the 20th, and were soon cemented as The-with-a-capital-T Old Fashioned.
The official story is that the cocktail we know today as the Old Fashioned was invented in the 1880’s at Louisville’s own aforementioned Pendennis Club, by a bartender and whiskey magnate called James Pepper. He invented the drink and mixed the very first one in Louisville, and he later brought it up to New York’s City’s Waldorf-Astoria, where it really made its name (The old fashioned apparently has a similar life trajectory to Zelda’s and mine, fancy that).
In 1885, George Kappeler published Modern American Drinks, which included the recipe for The Old Fashioned Whiskey Cocktail: “Dissolve a small lump of sugar with a little water in a whiskey-glass; add two dashes Angostura bitters, a small piece of ice, a piece of lemon-peel, one jigger whiskey. Mix with small bar-spoon and serve, leaving spoon in glass.” And essentially, that was that. The recipe has been slightly modified back and forth since then, but has stayed relatively close to the original.
In the 1930’s, the orange peel and cherry garnish were introduced, instigating turmoil among drinkers over what actually makes the perfect old fashioned. But you know you’ve got a good bartender when they ask “How do you like your old fashioned” after you order. Whether you stick to the traditional four-ingredient base, or add some orange zest, or take yours with brandy like they do in Wisconsin, or I suppose even if you muddle yours with a maraschino cherry (*sigh*), the old fashioned, in some way, shape, or form — is here to stay.
The great thing about a classic cocktail is that there’s endless potential to put a new spin on it, and bars these days continue to seize the opportunity, making them with agave or sorghum or whatever they can find. We are, as they say, in the age of the craft cocktail, and you can be sure that the Old Fashioned is in no danger of becoming what its name might suggest. But if you’re making me one? Please, no cherries.
Zelda & Scout 
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