Combine the sugar, bitters and ½ teaspoon water in the bottom of a rocks glass and muddle with a muddler or gently smash with the wooden handle of a spoon or other kitchen implement until the sugar dissolves. Add the bourbon or rye and stir until well-mixed.
Using a vegetable peeler, remove a 3- to 4-inch long strip of zest from the orange. Immediately twist the peel directly over the drink, then run the pith side around the rim of the glass. Drop the twist into the glass and add one big ice cube or enough regular-sized ones to nearly fill the glass. Stir until the drink is very chilled, 20 to 30 seconds. Repeat as needed.
Stirred and Strained Old Fashioned: Stir the drink in a cocktail shaker with ice, then strain into a chilled rocks glass with ice.
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