For the Fudge: 1/4 cup unsweetened Dutch-processed cocoa powder 1/3 cup packed dark brown sugar 1/2 cup light corn syrup 2/3 cup heavy cream 1/4 teaspoon salt 6 ounces good dark chocolate (not unsweetened), finely chopped (I used Ghirardelli Intense Dark Chocolate) 2 Tablespoon unsalted butter, cup into small cubes 1 teaspoon vanilla extract For the Milkshake: 2 cups vanilla ice cream 1 cup whole milk 1 ounce bourbon (optional) 1 tablespoon pure vanilla extract For the Whipped Cream: 1/2 cup heavy cream 2 tablespoons powdered sugar 1 teaspoon pure vanilla extract
To Make the Fudge: Stir together cocoa powder, brown sugar, corn syrup, cream, salt and half of the chopped chocolate in a 2-quart heavy saucepan and cook over moderate heat, stirring, until chocolate is melted. Cook mixture at a low boil, stirring occasionally, for 5 minutes. Remove pan from heat, add remaining chocolate, butter and vanilla and stir until smooth. Cool slightly before serving. Cooled sauce can be refrigerated in an airtight container for up to 1 week. Reheat over how heat, stirring. To Make the Whipped Cream: In a medium bowl whisk together heavy cream, powdered sugar, and vanilla. Whisk by hand (because you have muscles) until soft peaks form. Allow to chill in the refrigerator while you blend the milkshake. To Make the Milkshake: In a blender (or milkshake machine) combine ice cream, milk, bourbon, and vanilla. Blend until thick and creamy. Add more ice cream to thicken to desired consistency or more milk to thin to desired consistency. To Assemble the Milkshake: Pour a few tablespoons of warm fudge into a tall glass. Top with milkshake. Dollop on whipped cream. Sprinkle with jimmies and chocolate. Cherry to top and serve immediately.