Make the crust: Place the 10 chocolate Oreos in a food processor and pulse until you have coarse crumbs. Add 1 tbsp melted butter and pulse again to combine. Divide the mixture evenly between 4 (8oz) mason jars. Press the crumbs down with a spoon or the end of a rolling pin to form a crust.
Prepare the cheesecake filling: In a large bowl, place 8 oz softened cream cheese. Whisk with an electric mixer for a few seconds to loosen. Add 1/2 tsp vanilla extract and 1/2 cup confectioners’ sugar. Stir gently, then whisk until smooth.
Whip the cream: In a separate bowl, whisk 1/2 cup heavy cream until soft peaks form. Fold the whipped cream into the cream cheese mixture gently.
Add the chocolate: Pour in 2.25 oz melted bittersweet chocolate and 2.25 oz melted semi-sweet chocolate. Stir until fully combined.
For easier layering, transfer the chocolate mixture into a plastic sandwich bag, snip off a corner, and pipe it into each mason jar over the Oreo crust. Tap the jars lightly to remove air bubbles.
Top with cherries: Place 3 fresh pitted cherries on top of the chocolate layer in each jar. Spoon 1–2 tablespoons of black cherry pie filling over the cherries.
Sprinkle with 2 tbsp grated semi-sweet chocolate.
Serve or store: Enjoy immediately, or cover with lids and refrigerate for up to 2 days. Serve chilled.