Add the cherries, vanilla ice cream, milk and bourbon to your blender, puree until smooth.
In a small saucepan over medium heat, add the chocolate and heavy cream. Bring to a simmer and low the heat, stirring until the chocolate is completely melted.
Pour 2 ounces of chocolate ganache in the bottom of 2 milkshake or Collins-style glasses and then divide the milkshake between each glass.