2 bags Pepperidge Farm Chessmen cookies (or three if you want a consistent top layer design!)
6 to 8 bananas, sliced
2 cups milk
1 (5-ounce) box instant vanilla pudding
1 (8-ounce) package cream cheese, softened
1 (14-ounce) can sweetened condensed milk
1 (16-ounce) container heavy whipping cream
1.5 tablespoons powdered sugar
2 tsp vanilla extract
Line the bottom of a 13 by 9 by 2-inch dish with 1 bag of cookies and layer bananas on top.
In a bowl, combine the milk and pudding mix and blend well using a handheld electric mixer. Using another bowl, combine the cream cheese and condensed milk together and mix until smooth. In yet another bowl mix the whipping cream, powdered sugar and vanilla until stiff peaks form. Fold the whipped topping into the cream cheese mixture. Add the cream cheese mixture to the pudding mixture and stir until well blended. Pour the mixture over the cookies and bananas and cover with the remaining cookies. Refrigerate until ready to serve.
I think this gets better with time so it would be a great make ahead dessert or if you like your cookies crispy make it right before you head out the door!