Process the cookies and granulated sugar in a food processor for 30 seconds or until finely ground. Add the butter; pulse 8 to 10 times or until combined. Press the mixture into bottoms of 8 (8-ounce) serving glasses (or small canning jars).
Microwave the chocolate in a medium-size, microwave-safe bowl 50 seconds to 1 minute or until melted and smooth, stirring after 30 seconds. Let cool slightly.
Beat the cream cheese with a mixer at medium speed 2 to 3 minutes until fluffy. Add the vanilla, salt, and melted chocolate, beating at low speed until well blended.
Beat the whipping cream until foamy; gradually add the powdered sugar, beating until soft peaks form. Fold the whipped cream into the chocolate mixture. Spoon into the glasses. Cover and chill 4 hours or until set.
For the topping, cook the cherries and sugar in a small saucepan over medium 5 minutes or until the sugar dissolves. Stir the cornstarch with 1 tablespoon water in a small bowl. Stir into the cherries; cook, stirring frequently, 5 minutes or just until thickened. Remove from the heat. Stir in the orange liqueur (or orange juice) and salt. Let cool.
Top each serving with a layer of whipped cream and the Cherry Topping to serve.