Preparation
Add the sugar and bitters into a mixing glass, then add the water, and stir until the sugar is nearly dissolved.
Fill the mixing glass with ice, add the bourbon, and stir until well-chilled.
Strain into a rocks glass over one large ice cube.
Garnish with an orange twist and a cherry.
History
The first documented definition of the word "cocktail" was in response to a reader's letter asking to define the word in the 6 May 1806, issue of The Balance and Columbian Repository in Hudson, New York. In the 13 May 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 and is essentially the recipe for an old fashioned. 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.