Preheat the oven to 350 degrees.

Crush 1½ bags of Chessman cookies using a food processor or by hand in a zip-top bag.

In a medium bowl, mix the crushed cookies with 4 tablespoons melted butter until evenly coated.

Press the mixture firmly into the bottom of a 9×13-inch casserole dish.

Bake for 8–10 minutes until lightly golden. Let cool completely.

In a dry skillet over medium heat, toast ½ cup chopped pecans for 4–6 minutes, stirring frequently, until fragrant and golden. Set aside to cool.

In a large mixing bowl, combine milk and instant pudding mix.

Mix with an electric hand mixer on low speed for about 2 minutes until thickened.

In a separate large bowl, beat softened cream cheese and sweetened condensed milk on medium-high speed until smooth and lump-free.

Gently fold the thawed whipped topping into the cream cheese mixture using a rubber spatula.

Once combined, fold in the pudding mixture until fully incorporated.

Layer banana slices evenly over the cooled cookie crust.

Sprinkle half of the toasted pecans over the bananas.

Spread the cream mixture over the bananas and smooth it into an even layer.

Crush the remaining ½ bag of cookies and sprinkle them over the top.

Finish by sprinkling the remaining toasted pecans for garnish.

Cover with plastic wrap and refrigerate for at least 3 hours, or ideally overnight, to allow flavors to meld and layers to set.