In a medium bowl, combine the crushed Oreo cookies and melted butter. Mix until the crumbs are well coated and resemble wet sand.
Divide the Oreo mixture evenly among serving cups (about 1.5 tablespoons per cup), pressing it down firmly to create a crust layer on the bottom.
In another large bowl, beat the softened cream cheese using an electric mixer until smooth and creamy.
Add the powdered sugar and vanilla extract to the cream cheese, mixing until fully incorporated and smooth.
In a separate bowl, whip the heavy cream until stiff peaks form. Gently fold the whipped cream into the cream cheese mixture using a spatula until well combined, being careful not to deflate the whipped cream.
Spoon the cream cheese mixture over the crust in each cup, smoothing the top with a spatula.
Refrigerate the cheesecake cups for at least 4 hours, or until set.
Before serving, top each cup with additional crushed Oreo cookies or a whole Oreo for garnish.