Crush the Oreos: Place the Oreos in a large Ziploc bag and crush them with a rolling pin or use a food processor to get fine crumbs. Set aside.

1. Prepare the cream filling: In a large bowl, beat the softened cream cheese with an electric mixer until smooth and creamy. Add the powdered sugar and vanilla extract, and mix until well combined.
2. Whip the cream: In a separate bowl, whip the heavy whipping cream and ½ cup powdered sugar with an electric mixer until stiff peaks form.
3. Combine the cream filling: Gently fold the whipped cream into the cream cheese mixture, being careful not to deflate the whipped cream.
4. Assemble the cups: In individual dessert cups or mason jars, layer the crushed Oreos at the bottom, followed by a generous layer of the cream filling. Repeat the layers, finishing with a layer of the cream filling on top.
5. Chill the dessert: Refrigerate the Oreo Dessert Cups for at least 2 hours to allow the flavors to meld and the layers to set.
6. Garnish and serve: Just before serving, garnish the top with extra crushed Oreos, chocolate syrup, or mini chocolate chips for added texture and flavor. Serve chilled.