To prepare the crust, combine cookie crumbs, butter and sugar in a medium bowl. Press into the bottom of a 9-inch springform pan. Refrigerate while you prepare the filling.
In a separate bowl, beat the cream cheese and 1/3 cup sugar until smooth. Mix in sour cream and vanilla. Fold in the Cool Whip.
Spread half of the cream cheese mixture over the prepared crust. Freeze while you prepare the chocolate layer.
In a microwave safe bowl, melt the chocolate with the milk at 50% power until smooth. Cool to lukewarm. Stir the chocolate into the remaining cheesecake filling.
Spread the chocolate filling over the vanilla filling. Cover and refrigerate for 4-6 hours, or until firm. Before serving, top with cherry pie filling.