Begin by finely crushing 24 Oreo cookies with a tablespoon of granulated sugar in a food processor. Incorporate 6 tablespoons of melted, slightly cooled unsalted butter, pulsing until the crumbs are uniformly moistened. Firmly press this mixture into a 9-inch pie dish, forming an even layer for the crust. Chill the crust for at least 30 minutes, or up to 12 hours, to ensure it sets perfectly.
Preheat your oven to 350°F (175°C) and toast ½ cup of raw pecans on a baking sheet until they are fragrant and lightly browned, typically 13-17 minutes. Allow them to cool before finely chopping. For the fudge filling, combine ¼ cup plus 1 tablespoon heavy cream, 3 tablespoons chilled unsalted butter, 2 tablespoons light corn syrup, and ½ teaspoon Diamond Crystal or ¼ teaspoon Morton kosher salt in a small saucepan. Bring to a simmer over medium heat, then pour the mixture over 4 ounces of coarsely chopped bittersweet chocolate in a heatproof bowl. Let it sit for one minute, then whisk until smooth. Stir in 1 cup (110g) of sifted powdered sugar and 1 tablespoon of bourbon until the mixture is smooth. Spread this rich fudge evenly over the chilled crust and refrigerate for 2 hours.
Soften 1 pint of coffee ice cream by microwaving it in 10-second intervals for a total of 20-30 seconds until it becomes pliable. Transfer the softened ice cream to a large bowl and mix with a rubber spatula until it reaches a slightly malleable consistency. Spread the ice cream evenly over the chilled fudge layer. Sprinkle the toasted, chopped pecans over the ice cream, gently pressing them into the surface. Freeze the pie for 1-2 hours, or until the ice cream is firm.
Prepare the topping by bringing 2 tablespoons heavy cream, 2 tablespoons unsalted butter, 1 tablespoon light corn syrup, and ¼ teaspoon Diamond Crystal or Morton kosher salt to a gentle simmer in a small saucepan over low heat. Remove from heat and whisk in 3 ounces of coarsely chopped bittersweet chocolate until it's completely melted and smooth. Stir in 1 teaspoon of bourbon. Allow the topping to cool slightly, then artfully drizzle it over the ice cream and pecan layers in a crosshatch pattern. Freeze the pie for an additional 20 minutes to set the topping.
Before serving, an optional sprinkle of flaky sea salt can be added to enhance the flavors. Use a warm, sharp knife to cut the pie into elegant slices. This Mississippi Mud Pie is an ideal dessert for advance preparation; it can be made up to 4 days ahead. Simply wrap it tightly and store it in the freezer until ready to enjoy.
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