Line the bottom of a 9x13 inch dish with one bag of cookies. Lay them flat in a single layer. Make sure the bottom is fully covered. This creates a solid, buttery base for your pudding.

Peel your bananas and slice them into thin rounds. Spread the slices evenly over the cookie layer. Use enough bananas so every bite has fruit. I usually use about seven large bananas for this step.

In a medium bowl, combine the cold milk and the instant pudding mix. Use a whisk to blend them together. Let it sit for five minutes. It should become thick and smooth before you move on.

In a separate large bowl, beat the softened cream cheese. Add the sweetened condensed milk slowly. Mix until the texture is completely smooth. There should be no lumps left in the bowl at all.

Gently fold the thawed whipped topping into the cream cheese mixture. Use a spatula for this part. Do not overmix it. You want the mixture to stay light and fluffy for the best result.

Add the prepared vanilla pudding into the cream cheese mixture. Stir them together until the color is even. The result should be a thick, pale yellow cream. It smells amazing at this point!

Pour the creamy mixture over the bananas and cookies. Use your spatula to spread it to the edges. Ensure all the bananas are covered. This keeps the fruit from turning brown too quickly.

Take the second bag of Chessmen cookies. Arrange them neatly on top of the pudding layer. You can make a pretty pattern with them. Press them down very lightly so they stick.

Cover the dish with plastic wrap. Place it in the fridge for at least four hours. Overnight is even better. The cookies will soften slightly while the pudding becomes firm and cold.