Preheat oven to 400 degrees. Let pie crust sit out for 10 minutes; unroll onto pie plate. Poke holes in the bottom of crust with a fork, then bake for 10-12 minutes until golden brown. Let cool completely.

Mix pudding and milk on medium speed for 2 minutes; pour into a bowl and set aside. Don’t bother rinsing bowl before step 3.

Mix peanut butter, 1/2 cup powdered sugar, & 2 tablespoons heavy cream on medium-high speed for 1 minute; spoon into a separate bowl and set aside. Rinse & chill mixing bowl for a few minutes, then whip 2 cups heavy cream and 1/4 cup powdered sugar in chilled bowl until stiff peaks form.

Place Oreo cookies in a Ziploc bag and crush with rolling pin.

Assemble pie; first, spoon peanut butter mixture onto pie crust. Sprinkle half of crushed Oreos over peanut butter. Spoon chocolate pudding over top of Oreos. Spoon whipped cream over top of pudding. Chill at least 1 hour.