Pour the bourbon, lemon juice, and simple syrup into a 2-quart pitcher.
Stir for about 20 seconds, until the mixture looks cloudy and even, with no syrup pooling at the bottom.
Cover and refrigerate the pitcher for at least 30 minutes and up to 24 hours.
Fill each rocks glass with a single large ice cube.
Pour the whiskey sour mixture over the ice, filling each glass nearly to the rim.
Add a dash or two of bitters to the surface of each glass, then garnish with a lemon wheel and a cherry.
Good to Know
For the zero proof pitcher, replace the bourbon with 2 cups black tea brewed strong and cooled, and skip the bitters. The lemon and syrup carry the whole drink.