Outsider Cocktails: Classic Old Fashioned With Rye

by Jim Casey
photo by Outsider

While the Old Fashioned is a classic cocktail, it features plenty of palatable twists and turns. Bourbon or rye? Sugar cube or simple syrup? Orange peel or cherry (or both)? We recently shared a recipe for the cocktail that featured bourbon (as well as a sugar cube, bitters, and an orange peel). Today, we’re going to use an Old Fashioned recipe from Outsider’s Brandon Chesbro that features rye whiskey (as well as simple syrup, bitters, an orange peel, and a cherry).

Bourbon, among other requirements, uses a mash bill of at least 51 percent corn and is typically sweet on the palate, while rye whiskey uses a mash bill of at least 51 percent rye grain and is typically spicy on the palate. Both bourbon and rye are commonly used in the classic Old Fashioned, since both were readily available when cocktails began to gain traction in the early 1900s. Of course, whether you prefer bourbon or rye in your Old Fashioned is a matter of personal taste—but you should frequently test the waters whiskeys.

Let’s get mixing with Brandon’s recipe for the classic Old Fashioned with rye.

Ingredients: Classic Old Fashioned With Rye

Three of Brandon’s favorite rye whiskeys for Old Fashioned cocktails include Sazerac Rye, Old Forester Rye, and WhistlePig PiggyBack Rye.


Pour 2 oz. Old Forester Rye (3 oz. if you want it stronger) into an empty rocks glass (image 1). Add 2 dashes Angostura Orange Bitters (2). Add 2 dashes Angostura Aromatic Bitters (3). Next, add 1 tsp. simple syrup (4).

Add 1 maraschino cherry and stir (5). Gently add 1 large square ice cube and stir (6). Express orange peel oils into the drink (7). Rub orange peel around the rim of the glass (8) and add twisted peel to the glass.

Enjoy your Old Fashioned masterpiece.