Cut off the strawberry stems. Remove the inside of the strawberry with a small knife and spoon to create a cup for the filling.
Trim the pointed strawberry tip with your knife so the strawberry will stand upright. Place on a cookie sheet.
Make the OREO cheesecake filling by crushing the cookies with a food processor or place in a large zipper plastic bag and smash with a rolling pin. With a spoon, mix 1 package of softened cream cheese with the crushed cookies.
Spoon the OREO filling into the strawberries.
In another bowl, beat 8 ounces cream cheese, sugar, and vanilla with a mixer until fluffy.
Place the cream cheese mixture in a pastry bag and pipe into the top of the Oreo stuffed strawberries.
Refrigerate until ready to serve. Only make 4-5 hours before serving or your strawberries will get soggy.
Right before serving, garnish with a mini Oreo cookie or graham cracker. (cookies will get soggy if you add these too early)
If you only want the cheesecake stuffed strawberries. Omit the OREO cookies and only get 1 package of cream cheese.