Place one of the ice cubes in a rocks glass and sprinkle the sugar on top. Add the bourbon, and briskly mix the drink with a small stirrer or bar whisk until the sugar dissolves and the glass is nice and cold. Replace the half-melted ice cube with the remaining fresh ice cube. Add the bitters and serve with a cherry or twist of orange peel.
On Sweetness: If you are someone that likes drinking bourbon straight, go with 1 teaspoon of sugar. If you normally like sweeter cocktails, increase the sugar to 2 teaspoons. It will still be a strong drink, but for someone like me that usually prefers mixers, I find it makes it a more enjoyable experience. As with most cocktails, do what makes you happiest!
On Strength: As you see, there isn’t much in the way of a mixer in this cocktail. If the drink is too strong for your tastes, add a splash of cold still or sparkling water. I also like to throw in a splash of the juice from the cherry jar, but maybe that’s just me.