Place 40 Oreo cookies in the bowl of a food processor and pulse until finely ground. Reserve ½ cup of the Oreo cookie crumbs and set aside.
To the remaining cookie crumbs, add ½ cup melted butter and pulse to combine.
Press the cookie mixture into a greased and parchment-lined 9-inch springform pan. Cover the bottom and ¾ of the way up the sides with an even layer of pressed crumbs. Place the pan in the freezer to firm the crust while preparing the cheesecake layer.
In a medium mixing bowl, beat together the cream cheese, 1 cup of powdered sugar, vanilla extract, and pudding mix until thoroughly combined.
With the mixer running, slowly drizzle in 1 cup of heavy whipping cream, beating until smooth and fluffy.
Pour the remaining 2 cups of heavy whipping cream into a chilled mixing bowl. Beat at medium-high speed (either with a standing mixer whisk attachment or with a handheld mixer). When the whipping cream thickens to soft peaks, add in the remaining ⅓ cup powdered sugar.
Continue beating until whipped cream forms stiff peaks.
Fold one cup of the whipped heavy cream and the reserved cookie crumbs into the cream cheese mixture. If desired, you can also chop up a few extra Oreo cookies and fold them into the mixture for some bigger chunks.
Spread the cheesecake layer evenly into the prepared crust.
Top with the remaining whipped cream.
Chop 5 to 6 Oreo cookies and sprinkle around the outer edge of the top of the cheesecake (or decorate however you like!).
Place the cheesecake in the refrigerator for at least 4 hours or in the freezer for at least 2 hours to set.