It is the original American cocktail, with ingredients so simple—sugar, bitters, bourbon, water, ice—that making one might seem idiot proof. But the Old- Fashioned is fiendishly difficult to perfect; the elements need to blend harmoniously for the drink to come off. Feeling daunted? Fear not, the home bartender can get the knack of this elegant and refreshing drink with a little practice and patience.
First, a bit of history. The Old-Fashioned originated in Kentucky’s bourbon country in the late 1800s. Legend has it that a bartender at The Pendennis Club in Louisville whipped it up for a local bourbon distiller, Colonel James E. Pepper. Like the Manhattan, its whiskey-based cousin, which was also invented around the same time, the Old-Fashioned has seen many iterations over the years. Some barkeeps muddle cherry; some do not (more on this in a moment). Some use bourbon, the traditional whiskey component; others prefer the less sweet rye, which is my choice. It’s a matter of personal preference. Go to ten different bars, and you will get ten different riffs on this classic.
Here’s how I make mine: to start, you need the right glass, itself a crucial element to a perfect OF. The heavy-bottomed tumbler that takes its name from the drink feels just right in the hand, and shows off the amber hues of the whiskey that forms the backbone of the drink.
The glass is a triumph of form and function: the vessel gives you plenty of room at the base to muddle the ingredients. Place a sugar cube in the bottom of the glass—you can use simple syrup, but I prefer a cube, preferably demerara—and saturate it with Angostura bitters. (About 4-5 shakes.)
Then, fill the glass with a small amount of water, just enough to cover the cube. Using a wooden or metal cocktail muddler, crush the cube until it completely dissolves. It takes several minutes, and requires some persistence: you want no residual granules, which alter with the drink’s smooth finish.
Many Old-Fashioned recipes call for maraschino cherries to be muddled with the sugar, but I prefer mine with just an orange peel for the following reasons. First, the artificial dyes of the maraschino bring a tacky note to this most elegant of elixirs. Secondly, the cherry adds even more sweetness to a drink that some sneer at for being too sugary. Many of the newer generation of craft cocktail makers eschew muddled cherries. And I concur: leaving out the muddled cherry makes for a leaner, more lip-smacking drinking experience. The orange peel, however, brings a vital citrus tang to the affair, and melds beautifully with the clove and allspice notes of the bitters. (After they blend, take a whiff.)
Next, add the ice. Some prefer one big rock, which is fine; I use four medium cubes, which lend the drink a nice acoustic effect. Now, your build is coming together. It’s time to add the main ingredient, the whiskey. As noted above, I prefer rye. It is less sweet than bourbon, and brings a pleasantly spicy heft to the OF. Stir. You can garnish with an uncrushed cherry—Luxardo, if you must—and start sipping.
For me, the making and drinking of an Old-Fashioned is a meditative evening-time pleasure, to be taken reading the day’s news in a favorite chair.
Matthew is a freelance writer who has contributed to the The Guardian, The Los Angeles Times and Vogue along with many others. Based in New York, Matthew offers and in-depth view of being a gentleman stateside.