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Make the simple syrup by combining the light brown sugar and water in a small pot and cooking until the sugar has melted. Set aside to cool.
Add ice to a mixing glass, and top with bourbon, bitters, cherry syrup, and simple syrup. Stir to combine.
Strain into an old-fashioned glass with a large ice cube. Top with a cherry.
Twist the peel of an orange over the glass to express its oil, brush it around the rim of the glass, then add it to the cocktail.