The first documented definition of the word "cocktail" was in response to a reader's letter asking to define the word in the May 6, 1806, issue of The Balance and Columbia Repository in Hudson, New York. In the May 13, 1806, issue, the paper's editor wrote that it was a potent concoction of spirits, bitters, water, and sugar, a kind of bittered sling.
The first use of the specific name "Old Fashioned" was for a Bourbon whiskey cocktail in the 1880s, at the Pendennis Club, a gentlemen’s club in Louisville, Kentucky. The recipe is said to have been invented by a bartender at that club, and popularized by a club member and bourbon distiller, Colonel James E. Pepper, who brought it to the Waldorf-Astoria Hotel bar in New York City.
There is great contention on the proper way to make an Old Fashioned. The apparently earliest written recipe, from 1895, specifies the following: "Dissolve a small lump of sugar with a little water in a whiskey-glass; add two dashes Angostura bitters, a small piece ice, a piece lemon-peel, one jigger whiskey. Mix with small bar-spoon and serve, leaving spoon in glass.
Two recipes from the 1900s vary in the precise ingredients, but continue to omit the cherry expected in a modern Old Fashioned, as well as the top off of soda water contested by cocktail purists. Orange bitters were highly popular at this time and, for the second recipe, Curacao appears to have been added to increase the orange flavor