Make Pie Crust: In a food processor, grind cookies until fine crumbs form; add melted butter and process until combined.
Press cookie crumb mixture into the bottom of the pie pan and up the sides. Refrigerate at least 30 minutes.
Make Cherry Pie Filling: Melt Candy Melts in the microwave according to package instructions. Cool, stirring occasionally, until just warm to the touch without becoming solid, about 10 to 15 minutes.
Whip 1/2 cup heavy cream on high speed until soft peaks form, about 3-4 minutes; set aside.
On medium speed, beat cream cheese until fluffy, about 20 to 30 seconds. Add the melted candy melts; both the candy melts and cream cheese should be about the same temperature to avoid curdling.
Add the chopped cherries and beat until blended then fold in the whipped cream.
Spoon the filling into the crust and refrigerate until firm, at least 3 hours or overnight.
Make Topping: Before serving whip the remaining 1/2 cup heavy cream on high speed with an electric mixer until frothy and slightly thickened. Add powdered sugar and vanilla extract. Continue whipping until stiff peaks form.
Using a 1M tip, pipe rosettes around the edge of the pie. Garnish with the additional fresh cherries, if using.