The history of booze is, perhaps unsurprisingly, frequently hazy, confused, and debated. While the origins of certain iconic drinks can be attributed to a specific clever bartender at a single glorious place and time, many others are nearly impossible to trace.
Even the origin of the word cocktail has several explanatory stories from which a person could choose. I would, however, advise you to lean toward the well-researched explanation of cocktail historian David Wondrich: He argues that cock-tail was a (somewhat vulgar) slang term for something that would course through, give you a surge of energy, lift your spirits, and basically cock your tail up (in the sense of lifting it or making it jaunty) like a prancing horse’s. In England this was typically a spicy ginger libation, but in America it evolved into something considerably stronger.
We don’t know precisely how or when Americans began taking their medicinal shot of bitters (which originated as medicine) tempered with alcohol, sugar, and a bit of water, or when they began terming it a cocktail. But we do know that one of the earliest written references we can find comes from an 1806 edition of The Balance, and Columbian Repository, a conservative newspaper in upstate New York. In response to a reader questioning the off-handed mention of “cock tail” in a column from the week before, the editor explains, "Cock tail, then is a stimulating liquor, composed of spirits of any kind, sugar, water and bitters. It is vulgarly called a bittered sling…”
A cocktail, then, was just four key ingredients—the combination of which work together in wondrous alchemy—that should sound like a pretty familiar list: booze, bitters, sugar, water. This is exactly the cocktail a purist would now call an Old Fashioned, unsullied by muddled oranges or cherries or splashes of Sprite.
And we likely owe the name "Old Fashioned" to purists (or at least the change-averse). Four ingredients is a great jumping off point for creative additions, and the 1870s and 1880s saw bartenders adding dashes of this and splashes of that to the cocktail, delighting some but absolutely appalling others. Those who were put-off by the modern flourishes took to ordering an “old-fashioned whiskey (or other spirit) cocktail” to be sure they received a cocktail made to the original four-ingredient specifications.
But, purists aren’t really that fun are they? And, while I might not dare to call any of my Old Fashioned-inspired creations an "Old Fashioned,” lest I incite rage, I do see the Old Fashioned as a perfect starting place for trying an infinite variety of customizations.
1. Try changing your base spirit.
An old fashioned cocktail originally could use any spirit, so you most certainly can, too! Don’t like whiskey? Try gin, rum, brandy, apple brandy, tequila, you name it. You might discover something interesting.
Death & Co. in New York brought this old idea back with their, now oft-copied, Oaxacan Old Fashioned, which not only uses an unexpected base spirit, but actually combines two different base spirits; it’s mostly tequila with a little extra boost from smoky mezcal (their recipe calls for 1 1/2 ounces tequila, 1/2 ounce mezcal, 1 teaspoon agave nectar, and 2 dashes Angostura bitters, stirred with ice and garnished with a twist of orange peel. Yum.) And at Bar Agricole in San Francisco, you can sometimes find a velvety gin Old Fashioned made with St. George’s Rye Gin and a twist of citrus.
You can be even bolder and create your own new base spirit by infusing it with something else. No need to infuse a whole bottle of booze: Just take a cup of your base spirit, combine it with what you want to infuse it with (use 1/2 cup of chopped fruit or nuts or around 1 tablespoon of fresh herbs, spices, or tea) and let it infuse for 2 to 24 hours, giving it a little shake and tasting a tiny nip every couple hours to check its progress. Then strain it. This can add a nice flavor to your end drink without requiring as much extra sweetener as you might need to use if you were using an infused syrup.
2. Or change up your sweetener.
A lump of sugar is the original (an old Old Fashioned usually came with a little spoon to allow the drinker to keep stirring the drink until the sugar was fully dissolved), but a teaspoon or two of simple syrup dissolves more easily.
And once you’ve veered into syrup territory, it’s an easy step to try maple syrup (excellent with bourbon), honey (nice with blended Scotch or rye), or agave syrup (a good choice for agave spirits like tequila).
Or you could make a flavored syrup, which can be a less risky and more subtle than directly infusing your base spirit.
The purists will be crying for you to stop the insanity, but I suspect you’ll be having fun.
3. Then you can also change up your bitters.
One of the remarkable things with cocktails is that subtle changes in ingredients can make a big difference in the final drink, and so it is with changing your bitters. Angostura bitters have a way of harmonizing and augmenting the flavor in nearly anything, but there are so many exciting flavors of bitters, from orange to grapefruit-hops, to cherry-vanilla, to chocolate-mole, on the market, I think it’s totally worth exploring.
Or do all three! The more changes you make, the more you have to think about how the flavors will harmonize together in the final cocktail, but use your culinary common sense and don’t be afraid to tweak something until you like it.
At the cocktail room at our distillery, we’ve had a number of drinks that were inspired by the Old Fashioned, including one we called the “Old Cedar”—cedar wood aged gin with grapefruit-rosemary syrup and grapefruit bitters—as well as the "Cold Fashioned," a cocktail of cognac barrel aged aquavit with maple syrup and cherry-hazelnut bitters.
And here, while it’s still summer, is a very tropical rum-based variation on an Old Fashioned!
For the drink:
2 1/2 ounces dark Rum
1 to 2 teaspoons roasted pineapple syrup (see below)
2 dashes Angostura bitters
For the roasted pineapple syrup:
1 whole ripe pineapple
2 1/2 cups sugar
Second and third photo by Bobbi Lin; last photo by Emily Vikre; all others by James Ransom