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 Columbian 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; it was also referred to at the time as a bittered sling. J.E. Alexander describes the cocktail similarly in 1833, as he encountered it in New York City, as being rum, gin, or brandy, significant water, bitters, and sugar, though he includes a nutmeg garnish as well
By the 1860s, it was common for orange curaçao, absinthe, and other liqueurs to be added to the cocktail. The original concoction, albeit in different proportions, came back into vogue, and was referred to as "old-fashioned”. The most popular of the in-vogue "old-fashioned" cocktails were made with whiskey, according to a Chicago barman, quoted in The Chicago Daily Tribune in 1882, with rye being more popular than Bourbon. The recipe he describes is a similar combination of spirits, bitters, water and sugar of seventy-six years earlier.
Traditionally, the first use of the name "Old Fashioned" for a Bourbon whiskey cocktail was said to have been, anachronistically, at the Pendennis Club, a gentlemen's club founded in 1881 in Louisville, Kentucky. The recipe was said to have been invented by a bartender at that club in honour of Colonel James E. Pepper, a prominent bourbon distiller, who brought it to the hotel bar in New York City.