1. Prepare the Base: In a bowl, combine the crushed chocolate sandwich cookies with the melted unsalted butter. Mix until well combined, resembling wet sand.
2. Create the Crust: Press about 1-2 tablespoons of the cookie mixture into the bottom of 12 small cups, glasses, or ramekins. Use the back of a spoon to firmly press and create an even layer. Chill for at least 10 minutes while you prepare the filling.
3. Make the Cream Filling: In a separate bowl, beat together the softened cream cheese, sweetened condensed milk, vanilla extract, and sifted powdered sugar until smooth and creamy. If using, stir in the 2 tablespoons of cherry juice for extra flavor.
4. Assemble the Layers: Spoon a generous layer of the cream cheese mixture over the chilled cookie crust in each cup. Smooth the top.
5. Add the Cherries: Top the cream cheese layer with a spoonful of drained, pitted cherries in each cup.
6. Prepare the Whipped Topping: In a chilled bowl, whip the cold heavy whipping cream until stiff peaks form. Be careful not to over-whip.
7. Top with Whipped Cream: Dollop or pipe the whipped cream over the cherries in each cup.
8. Garnish: Sprinkle with chocolate shavings or mini chocolate chips and top with a reserved cherry for garnish.
9. Chill: Refrigerate the mini cups for at least 30 minutes before serving to allow the flavors to meld and the dessert to set.