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Heaven in a pie plate starts with a creamy cheesecake-like filling. Buttery pecans, coconut, and crunchy Oreos are all tied together with some salted caramel so there's something heavenly in every bite.
Gather all ingredients.
Remove 20 of the cookies from 1 of the packages of chocolate cookies; set aside. Working in 2 batches, process remaining cookies (about 30 oz.) in a food processor until crushed into very fine crumbs, about 30 seconds. Transfer crumbs to a large bowl and add salt. Microwave 1 cup of the butter in a heatproof bowl on HIGH until melted, 30 to 60 seconds. Add melted butter to crumb mixture and stir until well combined.
Transfer crumb mixture to 2 ungreased deep dish (9- to 9 1/2-inch) pie plates (about 3 cups per plate); firmly press crumbs into bottom and up sides of pie plates. Freeze crusts, uncovered, until firm, about 20 minutes.
Meanwhile, melt remaining 1/4 cup butter in a large skillet over medium. Add pecans; cook, stirring often, until fragrant, 1 to 2 minutes. Stir in coconut; cook, stirring constantly, until toasted and golden, about 4 minutes. Transfer to a large baking sheet; spread in an even layer. Let cool completely to room temperature, about 20 minutes.
Beat together sweetened condensed milk, cream cheese, and vanilla in a large bowl with an electric mixer on high speed until smooth, about 1 minute. Stir in 1/2 container of the whipped topping to lighten the cream cheese mixture. Gently fold in remaining 1 1/2 containers whipped topping in 3 batches until just combined.
Spoon about 2 cups of the cream cheese mixture into each cooled pie crust; spread into an even layer with an offset spatula. Drizzle about 1/3 cup of the caramel sauce on each cream cheese mixture in crusts; gently swirl into cream cheese mixture. Sprinkle 1 cup of the cooled coconut mixture on top of each pie. Coarsely crumble 5 of the reserved cookies onto each pie in an even layer. Repeat layers once more with remaining 4 cups cream cheese mixture, 2/3 cup of the caramel sauce, remaining 2 cups cooled coconut mixture, and remaining 10 cookies. Drizzle with remaining about 1/3 cup caramel sauce evenly over top both pies.
Cover with plastic wrap and freeze until firm, at least 4 hours or up to 24 hours. When ready to serve, remove pie from freezer and allow to stand at room temperature for 10 minutes before slicing.