Prep your cups. Set out 8–10 small serving cups or jars.
If you like neat layers, choose clear glass to show them off.
Make the Oreo crust. Add 14 Oreo cookies to a food processor and pulse into fine crumbs. (No processor? Seal in a bag and crush with a rolling pin.) Mix crumbs with the melted butter until they resemble damp sand.
Press the base. Spoon 1–2 tablespoons of crumbs into each cup. Press down firmly with the back of a spoon.
Aim for a tight, even base so it holds together.
Crush Oreos for the filling. Roughly chop or crush 6 Oreos into chunky pieces. You want bits for texture, not powder.
Beat the cream cheese. In a large bowl, beat the softened cream cheese with a hand mixer until smooth and fluffy, about 1–2 minutes. No lumps—this is key.
Add sugar, vanilla, and salt. Beat in the powdered sugar, vanilla, and salt until creamy.
Scrape the bowl so everything blends evenly.
Whip the cream. In a separate chilled bowl, whip the cold heavy cream to stiff peaks. It should hold its shape when you lift the beaters.
Fold it together. Gently fold the whipped cream into the cream cheese mixture in two additions. Keep it airy.
Then fold in the crushed Oreo pieces.
Fill the cups. Spoon or pipe the cheesecake filling over each crust, leaving a little room on top for garnish.
Top and chill. Crush the remaining 4 Oreos and sprinkle over the cups. Add mini chips or a light drizzle of chocolate sauce if you want. Chill for at least 2 hours, or 30–45 minutes in the freezer for a quicker set.
Serve. Enjoy straight from the fridge for the best texture.
The filling will be silky and spoonable, not stiff.