Prep Time

　　2 minutes

　　Total Time

　　2 minutes

　　The invention of the classic old-fashioned is frequently (and probably inaccurately) credited to a bartender at the Pendennis Club in Louisville, Kentucky, who, around the turn of the 20th century, reportedly made the drink for Colonel James E. Pepper, a member of the club and by some accounts a prominent bourbon distiller.

　　There’s a strikingly similar cocktail in Jerry Thomas’s 1862 How to Mix Drinks, or the Bon-Vivant’s Companion, called the Whiskey Cocktail. What probably happened at Pendennis, says Robert Hess, founder of drinkboy.com and cofounder of the Museum of the American Cocktail, was that the bartender served a Whiskey Cocktail made the old-fashioned way—that is, the spirit combined with sugar, bitters, and water, the way cocktails were made as early as 1806.  

　　Like a manhattan or a martini, the best old-fashioned recipe for you is the one you love. It’s a stirred drink generally made right in the glass you’ll sip it from. Some prefer to swap the simple syrup for a muddled sugar cube or granulated sugar (doused in the warmly spiced Angostura bitters). That allows the flavor to evolve as you sip your way down the drink, starting bracingly strong and winding up softer and sweeter. A careful muddle is needed to prevent grit. You could also play around with the sweetener, using maple syrup or even the liquid from a jar of cocktail cherries instead. As for the bitters, making a simple old-fashioned cocktail with a different brand of aromatic bitters—or even swapping them out for Peychaud’s, orange bitters, or whatever you fancy—is a wonderful way to observe how the different seasonings play along in a drink.

　　An orange peel (or lemon peel) garnish, expressed over the top of the drink and then dropped in, offers citrusy aroma and a touch of bitterness to balance the drink, while an orange slice moves things into juicier territory. Some love bourbon here, others prefer peppery rye whiskey—either way, it improves the drink to start with higher-proof spirits. (Here’s our guide to the best whiskey for cocktails and sipping.) Swap in gin for the whiskey in the old-fashioned recipe below, and you’ll have an excellent gin old-fashioned. For more variations, see this guide to riffing on classic cocktail recipes—and a list of more essential classic cocktails to try at home.

Ingredients

　　⅛ oz. simple syrup

　　2 dashes Angostura bitters, plus more to taste

　　1 half dollar-size slice orange peel, including pith

　　2 oz. good-quality rye or bourbon

　　1 maraschino cherry (preferably a Luxardo cherry)

　　In an old-fashioned glass, combine ⅛ oz. simple syrup and 2 dashes Angostura bitters. Fill glass halfway with ice, then stir about a dozen times. Add enough ice to fill glass. Squeeze 1 half dollar-size slice orange peel, including pith, over glass to extract oils, add peel to glass, then add 2 oz. good-quality rye or bourbon. Stir just until drink is cold and the bite has softened, about a dozen times. Garnish with 1 maraschino cherry (preferably a Luxardo cherry). 

　　Editor’s note: This old-fashioned recipe first appeared on Epicurious in August 2006. Head this way for more of our favorite easy cocktail recipes →