"The original Old Fashioned recipe would have used whiskeys available in America in the late 1800’s, either Bourbon or Rye Whiskey. The first recipe is from 1895. But in some regions, especially Wisconsin, brandy is substituted for whiskey (sometimes called a Brandy Old Fashioned). Eventually the use of other spirits became common, such as a gin recipe becoming popularized in the late 1940s. The first mention of the drink was for a Bourbon whiskey cocktail in the 1880s, at the Pendennis Club, a gentlemen’s club in Louisville, Kentucky.
Common garnishes for an Old Fashioned include an orange slice or a maraschino cherry, although these modifications came around 1930, sometime after the original recipe was invented. The practice of muddling orange and other fruit gained prevalence as late as the 1990s. In muddling the fruit make sure to muddle the fruit but try not to muddle the peel too much. You want to release the oils and fruit flavor but not a lot of the acid. As with spirit only drinks what whiskey/brandy you make this drink with matters. The fun is in trying to find which one you really like!
Drop sugar cubes, water and angostura bitters in an old-fashioned glass. Drop in a cherry and an orange wedge. Muddle into a paste using a muddler or the back end of a spoon. Pour in bourbon, fill with ice cubes, and stir. To muddle, you want to gently smash the fruit and sugar so release the flavors before adding the spirits.