Place 8 of the Oreo cookies in a food processor and crush them into fine crumbs. Reserve 4 Oreo cookies to crush into larger chunks for topping or layering.

Divide half of the finely crushed Oreo crumbs evenly into the bottoms of serving cups or glasses to create the base layer.

In a large mixing bowl, beat the softened cream cheese with powdered sugar and vanilla extract until smooth and creamy.

In a separate bowl, whip the heavy whipping cream with granulated sugar until stiff peaks form.

Gently fold the whipped cream into the cream cheese mixture until fully combined and fluffy.

Spoon or pipe the cheesecake filling over the Oreo crumb base in each cup, filling the cups about halfway.

Layer the remaining finely crushed Oreo crumbs or larger Oreo chunks over the cheesecake filling as desired.

Top with another layer of cheesecake filling until the cups are full.

Garnish with extra crushed Oreos or Oreo halves, if desired.

Refrigerate the cups for at least 2 hours to set before serving.