Place one package of the Chessman cookies on the bottom of a 9X13 baking dish. They can overlap a bit.
2 packages Pepperidge Farm Chessman Cookies
Top the cookies with sliced bananas in a nice layer.
6 bananas
Beat the softened cream cheese and sweetened condensed milk until smooth.
1 cup cream cheese, 1 (14 ounce) can sweetened condensed milk
Add the dry pudding mix to the bowl and beat.
1 (5 ounce) box Instant Banana Pudding
Add the vanilla and milk and blend until smooth. Scrape down the sides of the bowl to mix evenly.
1 teaspoon vanilla extract, 2 cups whole milk
Carefully fold in the Cool Whip and then spread the mixture evenly over the top of the sliced bananas.
5 cups (about 12 ounces) Cool Whip
Top the pudding mixture with the rest of the Chessman cookies.
Cover the baking dish and place in the fridge. Let it chill for a minimum of 4 hours.
Remove from the fridge. Slice, and enjoy!