Take a quick scan through Robert Simonson’s book “The Old-Fashioned: The Story of the World’s First Classic Cocktail, with Recipes and Lore” and you’ll immediately learn one thing: The Old Fashioned has a history rich in ancestral recipes, regional styles, and modern-day offshoots. While we love riffs on the classic, such as the Calvados Old Fashioned and the variety inspired by Oaxaca, we also believe that if ain’t broke, don’t fix it.
For this list, we looked to the different styles of the tried-and-true cocktail. The drinks that qualify helped lead to the modern-day Old Fashioned or closely resemble the cocktail in its most classic form, giving us a canon of Old Fashioned-esque concoctions plus some regional takes on the bourbon-and-bitters drink. Even if the classic Old Fashioned is your Platonic ideal of a cocktail, try out this mix of seven styles — maybe one will become your New Fashioned.
Whiskey Cocktail (Bittered Sling)
The Whiskey Cocktail — also known as the Bittered Sling — is a direct ancestor of the Old Fashioned. It was first developed in the 1800s, and one of the earliest recipes is found in “Jerry Thomas’ Bartender’s Guide: How to Mix Drinks,” the first published cocktail book in English. This might be the oldest ancestor of the Old Fashioned, but it’s closer to what we know as the classic cocktail today than the later recipes (see below) that helped develop it. The Whiskey Cocktail calls for gum syrup, but if gum syrup is out of reach, Simonson says simple syrup will do. For the booze, the measurement is half a “wine-glass of whiskey,” the equivalent of 2 ounces, according to Simonson. It’s rounded out with a few dashes of bitters and some crushed ice — or, as Thomas called it, “fine ice” — for mixing.
Improved Whiskey Cocktail
Like many other mixologists in the 1800s, once Maraschino liqueur and absinthe trickled into the U.S. market, Thomas crafted an “improved” version of his already-established Whiskey Cocktail. For this recipe, Thomas specifies “rye or bourbon” as the spirit. While that gets us closer to today’s Old Fashioned recipe, the rest of this mix gets a bit wild. It calls for Maraschino liqueur, simple syrup, absinthe, and both Peychaud’s and Angostura bitters. The absinthe adds a boozier kick and, with it, a sweet anise flavor.
Old Fashioned Whiskey Cocktail
This account of the Old Fashioned Whiskey Cocktail likely came about due to a journalistic faux pas. According to Simonson, in 1908, a reporter for the New York Sun attributed this recipe — which includes nutmeg — to famed bartender Jim Gray, who became a popular mixologist in New York City thanks to his work at Astor House and the Fifth Avenue Hotel. Other bartenders were skeptical about the autumnal spice’s inclusion and wrote to the paper that the reporter must have mistaken Gray’s Whiskey Toddy recipe for his Old Fashioned Whiskey Cocktail. But as the saying goes, “journalism is the first rough draft of history,” and this account cemented Gray’s Old Fashioned style within the cocktail canon. It uses bourbon or rye and a sugar cube muddled with water and nutmeg. The ensemble is mixed with ice, strained, and poured into an Old Fashioned glass and then dressed up with an additional dusting of nutmeg. There’s remarkably no mention of a citrus peel garnish or any inclusion of bitters.
Old Fashioned Cocktail Method 1
Bartender Theodore Proulx published the first-ever Old Fashioned recipe in his 1888 book “Bartender’s Manual.” This mix is similar to Gray’s version with an added dash of absinthe. It also includes sugar dissolved in water, Angostura bitters, simple syrup, and whiskey. A lemon peel garnish is added to the liquid before mixing for a bigger citrus presence.
Old Fashioned Cocktail Method 2
Proulx’s second method for the Old Fashioned, as outlined in his manual, is much more recognizable than the primary one. Just like the first method, this recipe begins with a sugar cube dissolved in water. From there, Angostura bitters, simple syrup, whiskey, and a lemon peel get mixed with ice to create the cocktail.
Pendennis Club Old Fashioned
It’s a common legend in the cocktail community that the modern Old Fashioned recipe comes from a social club in Louisville, Ky., called the Pendennis Club, but it is a widely contested claim. Regardless of its origin, the club’s version is still one to try. It calls for muddling some orange, a lemon peel, and a seedless cherry with simple syrup and bitters. From there, mix in the bourbon — from Kentucky, obviously — and some ice.
Brandy Old Fashioned (Wisconsin Style)
The Brandy Old Fashioned is better known as the Wisconsin Old Fashioned, and given its unofficial moniker, it is one of the most popular orders in the Midwest. As the name implies, the most notable inclusion in the Brandy Old Fashioned is — you guessed it — brandy. What makes it of the Wisconsin variety is the use of Korbel. Simonson says if you don’t have access to it, any domestic, light-bodied brandy will do. The drink also calls for a sugar cube muddled with Angostura bitters, lemon lime soda, and two maraschino cherries as the garnish.
