Line your baking dish with parchment paper. Secure with binder clips or clothes pins and set aside.
Finely chop 5 of the Oreos and set aside. Place the remaining 9 Oreos in a plastic bag and crush into a fine crumb with a rolling pin or the bottom of a glass. Pour crumbs into a medium bowl and stir in melted butter until well mixed. Pour crumbs into prepared baking dish and press out into an even layer.
In a medium bowl, use a handheld electric mixer to beat heavy cream until stiff peaks form (when you lift the beaters straight up, the peaks should stand straight up without flopping over). Set aside.
In a medium bowl, beat softened cream cheese, sugar, and vanilla until well mixed. Fold in whipped cream and Oreos, being careful not to deflate the whipped cream. Transfer mixture to your prepared dish and spread over crust. Cover and freeze until firm, about 3 hours.
Use the parchment paper to remove cheesecake from the container and cut into 24 small squares. Add a dollop of whipped cream to each if desired, and enjoy!
Notes
Store airtight container in the refrigerator for up to 3 days or in the freezer for 2 to 3 weeks.Approximate nutritional information is per bite and does not include optional whipped cream topping. *To make additional whipped cream for topping the bites, beat together 1/3 cup cold heavy cream and 2 teaspoons granulated sugar until stiff peaks form. Transfer to a piping bag and pipe small dollops over the bites.