Preheat the oven to 350°F (177°C). Ensure the center oven rack is ready for baking the cookie crust.
Grind 22 whole Oreo cookies into fine crumbs in a food processor, stir in 5 tablespoons of melted unsalted butter, and press the mixture firmly across the bottom and up the sides of an ungreased 9-inch pie dish. Bake for 10 minutes until the crust is fragrant and set, then let it cool completely on a wire rack.
Heat 3/4 cup of heavy cream in a small saucepan over medium heat until it simmers, then pour it immediately over 6 ounces of finely chopped semi-sweet chocolate in a heat-proof bowl. Let the bowl sit untouched for 2 to 3 minutes, then stir gently until the ganache turns smooth, glossy, and slightly thick at room temperature.
Whip 1 cup of cold heavy cream on medium-high speed for about 3 minutes until stiff peaks form, transfer it to a separate bowl, then beat 8 ounces of softened cream cheese, 1 and 1/2 cups of creamy peanut butter, 3/4 cup of confectioners’ sugar, and 1 teaspoon of vanilla extract in the mixer bowl until thick and smooth. Fold the whipped cream into the peanut butter mixture gently with a silicone spatula until no white streaks remain.
Spread the peanut butter filling evenly across the bottom of the cooled crust using a small offset spatula. Level the top surface so the chocolate ganache distributes evenly across the pie.
Pour the cooled chocolate ganache directly over the peanut butter filling and smooth it outward to the crust edges. The ganache should create a satiny, even layer across the entire top surface.
Scatter 1/4 cup of crushed Reese’s Pieces and 1/4 cup of chopped peanuts over the wet ganache if skipping piped whipped cream garnish. Pressing dry toppings into the unset ganache anchors them securely in place before refrigeration.
Transfer the assembled pie to the refrigerator to chill for at least 6 hours or up to 48 hours. Cover the pie loosely if storing it chilled for longer than a single day to protect the dairy from absorbing odors.
Pipe decorative whipped cream rosettes over the chilled ganache using a star piping tip, then scatter crushed candies and chopped peanuts over top. The firm, chilled chocolate layer supports the piped cream without sinking.
Slice the pie while cold using a sharp knife and serve immediately. Cover remaining slices and return them to the refrigerator promptly for safe storage.