Place the cream cheese in a large bowl and allow it to reach room temperature.
In the meantime, melt the chocolate according to the package directions. Remove from heat source and let cool.
Gradually add the milk to the softened cream cheese and beat after each small amount until blended.
Add the dry pudding mix and cooled melted chocolate. Slowly beat until blended, approximately 1 minute.
Fold in whipped topping to keep the mixture light and fluffy.
Line a 9x5-inch loaf pan with parchment or wax paper. Create “handles” for easy removal by extending the paper over the sides.
Layer your cake by arranging ¼ of the cookies on the bottom of the pan.
Cover the cookies with 1/3 of the pudding mixture. Repeat layers twice.
Top with remaining cookies (or cookie crumbleand add your Halloween decorations.
Refrigerate for at least 5 hours.
Using your paper handles, slowly remove the cake from the loaf pan before serving individual slices.