This whiskey-and-Coke fandango is so chewy, dense, and rich, it’ll actually need the whipped cream to lighten it up. No, you don’t have to use Jack Daniel’s. It just seems as if you should. Certainly don’t use a fancy single malt. A blended whiskey will be fine, a nice depth of flavor. And one more thing: all the whiskey doesn’t “cook out” of the filling. Don’t kid yourself. This one’s for the adults who can partake.
Single-crust version of Shortening-Butter Crust
1½ pounds semisweet or bittersweet chocolate, chopped
11 tablespoons (1 stick plus 3 tablespoons) unsalted butter, cut into chunks
¾ cup whiskey, preferably Jack Daniel’s, plus additional as needed
⅔ cup cola (do not use diet soda)
2 cups granulated white sugar
10 large eggs, at room temperature
1 tablespoon vanilla extract
1 teaspoon salt
⅔ cup all-purpose flour
1½ cups dark chocolate chunks
2 cups jarred caramel or butterscotch caramel ice cream topping
1. Position the rack in the center of the oven. Heat the oven to 350°F.
2. Prepare and shape the crust as directed in a 13 × 18-inch lipped sheet pan. Prick the crust repeatedly with a flatware fork across the flat surface and up the sides.
3. Cover the crust with aluminum foil, pressing down gently to cover the exposed surface without smushing into the crust. Bake for 10 minutes. Transfer to a wire rack and remove the foil. Maintain the oven’s temperature.
4. Put the chocolate, butter, whiskey, and cola in a large saucepan over medium heat. Cook, stirring constantly, until about two-thirds of the chocolate has melted. Remove from the heat and continue stirring until smooth. Pour and scrape into a large bowl; cool to room temperature, about 30 minutes.
5. Using a handheld electric mixer or a stand mixer with the paddle attachment, beat the sugar into the chocolate mixture at medium speed until smooth and light, about 3 minutes. Beat in the eggs one at a time, then beat in the vanilla and salt until uniform.
6. Scrape down the inside of the bowl. Beat in the flour just until there are no dry specks anywhere. Scrape down and remove the beaters or paddle.
7. Use a silicone spatula to fold in the chocolate chunks. Pour and spread this batter into the prepared crust.
8. Bake until puffed and set, about 25 minutes. Cool in the pan on a wire rack until room temperature, about 1½ hours.
9. Whisk the caramel in a small bowl with just enough whiskey to create a sauce that can be drizzled off the tines of a flatware fork. Smooth the sweetened whipped cream over the top of the pie. Drizzle the caramel mixture over the cake before serving.