Whip the cream and vanilla until stiff peaks form.
Beat the cream cheese with the sugar until smooth and well blended. Fold the whipped cream into the cream cheese mixture. Remove a little less than half the mixture and combine it with the melted chocolate.
Place the chocolate cream cheese mixture into a food storage bag and snip off one of the corners. In another food storage bag, put the rest of the cream cheese mixture and snip off one of the corners.
Place 1 tablespoon of graham style cracker crumbs into the bottom of 8 small wine glasses, cordial glasses, or dessert tasting cups. Pipe the chocolate mixture into the cups, then pipe the cream cheese mixture on top of the chocolate. Dust the top of the desserts with cocoa powder and refrigerate for at least 1 hour. Can be made a day ahead.