Cook 1 cup sugar and 1 cup water in a small saucepan over medium-high heat 5 minutes, stirring until sugar dissolves. Remove from heat, and cool.
Pack a 3 1/2-ounce cocktail glass with ice cubes, and set glass aside.
Combine whiskey, bitters, sugar syrup, and a few ice cubes in a cocktail shaker; stir to chill.
Discard ice cubes in cocktail glass. Coat inside of glass with liqueur, shaking out excess liqueur. (For stronger licorice flavor, leave excess liqueur in glass.) Rub lemon rind over rim of glass, and discard rind.
Strain whiskey mixture into prepared glass. Serve drink immediately.
Note: For testing purposes only, we used Jim Beam Straight Rye Whiskey, Peychaud's Bitters, and Herbsaint anise liqueur. Rye whiskey is distilled from rye grain instead of wheat and barley, giving it a smooth, rich flavor similar to that of bourbon.
I had to use trial and error to figure out how much simple syrup to add. I finally settled upon 1/4 ounce. I personally like a bit extra anise, but I suggest you try the recipe as stated first. I didn't have rye, so I used bourbon and I garnished with cherries.