Hold an 8-ounce glass or jelly jar sideways, squirt in about a tablespoon or so of chocolate syrup about a quarter of the way down from the top and rotate the glass to coat the inside. Repeat with 5 more glasses and put in the freezer until ready to serve the milkshakes.
Whip the cream with 1 tablespoon bourbon and refrigerate until ready to serve.
Chop the chocolate bars finely. Remove the stems from 12 of the cherries and chop them finely.
Put the ice cream, milk, and ½ cup of bourbon in a blender and process until thick and smooth. Add the chopped chocolate and cherries and blend. Pour the mixture into the prepared glasses, top with whipped cream and a cherry and serve with a straw and a spoon.