Whip the cream, pudding mix, sugar, bourbon, and salt in the bowl of a stand mixer fitted with the whisk attachment until stiff peaks form. If desired, add a touch more bourbon. This will keep in the refrigerator for several days.

To make the pudding, bring the milk to a simmer over medium heat in a saucepan. In a medium bowl, whisk together the sugar, cornstarch, cocoa powder, salt, egg yolks, and egg. Once the milk simmers, temper it into the egg mixture by slowly streaming in the hot milk and whisking continuously. Pour the mixture back into the saucepan and bring it back to a simmer, stirring constantly with a wooden spoon or whisk. Once it thickens, remove from heat and add the chocolate chips and butter, stirring until both are melted. Cover the surface with plastic wrap to prevent skin from forming and allow it to cool.

For assembly, I use small cups for easy portioning and pastry bags to neatly pipe both the pudding and whipped cream. Put a layer of chocolate pudding at the bottom, followed by a sprinkle of cookies, a layer of whipped cream, and a sprinkle of mint chocolate candies. Repeat layering to fill the cups and refrigerate until ready to serve.