Prepare the Crust: If using homemade crusts, crush 24 chocolate Oreos into fine crumbs and mix with 6 tablespoons of melted butter. Press evenly into two 9-inch pie pans. Chill in the refrigerator while preparing the filling.
Crush the cookies: Set aside 8 mint cookies for garnish, then crush the remaining cookies into coarse crumbs.
Mix the filling: In a large bowl, beat the softened cream cheese until smooth. Add the sweetened condensed milk, mint extract, and green food coloring. Beat until fully combined and creamy.
Fold in Cool Whip: Gently fold in 8 ounces of Cool Whip and the crushed cookies until evenly incorporated.
Assemble the Pies: Divide the filling evenly between the two prepared pie crusts, spreading it into an even layer.
Melt the chocolate: In a microwave-safe bowl, combine the semi-sweet chocolate chips and heavy whipping cream. Microwave in 20-second intervals, stirring in between, until smooth and melted. Drizzle or spread the melted chocolate over the pies as desired.
Garnish: Crush the reserved cookies and sprinkle them on top of the pies. Optionally, dollop the remaining Cool Whip on top and garnish with cookie halves or additional mint candies for a festive touch.
Chill and Serve: Chill the pies in the refrigerator for at least 4 hours or overnight for the best texture. Slice, serve, and enjoy this creamy, minty dessert!