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For Chocolate Cookie Crust: Place cookies in food processor and blend until fine cookie crumbs are formed. Add melted butter, and pulse food processor 3-4 additional times. Spray a 9-inch deep dish pie plate with baking spray and press the cookie crumb mixture into the bottom and up the sides of the pie plate. Place pie plate in freezer to chill for 10-15 minutes.
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For Cappuccino Pie: Chill a large metal or glass bowl and wire whisk in the freezer for 15 minutes.
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Meanwhile, in a large bowl, whisk together milk, coffee, pudding mix and ½ cup heavy cream. Set aside.
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Add remaining 1½ cups heavy cream, powdered sugar and vanilla to chilled bowl. Using a large hand-held whisk or an electric mixer, whip cream until it begins to thicken. Continue to whip cream until soft peaks begin to form. Use caution and do not over mix.
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Fold half of the whipped cream mixture into the pudding mixture, being careful not to over mix. Pour pie filling into prepared pie crust and store remaining whipped cream in refrigerator until ready to serve.
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Place pie in freezer and freeze for 4-6 hours, or until frozen. When ready to serve, remove pie from freezer and let sit at room temperature for 15 minutes.
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Meanwhile, place 8-10 chocolate sandwich cookies in food processor and blend until large cookie crumbs are formed.
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Right before slicing, spread remaining whipped cream on top of pie and top with large cookie pieces. Slice and serve immediately.