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In a large bowl, prepare the Jell-O Vanilla Instant Pudding according to package directions, using 3 cups of cold milk. Whisk until well combined and slightly thickened. Set aside.

In a separate large bowl, beat the softened cream cheese until smooth and creamy. Gradually add the entire can of sweetened condensed milk, beating until fully incorporated and the mixture is light and fluffy.

Gently fold in the thawed Cool Whip into the cream cheese and condensed milk mixture until no streaks remain. Be careful not to overmix.

Combine the prepared vanilla pudding with the cream cheese and Cool Whip mixture. Mix gently until just combined. This will be your creamy topping.

To assemble the pudding, arrange approximately 16 Pepperidge Farm Chessmen Butter Cookies in a single layer at the bottom of a 9x13 inch dish.

Layer half of the sliced bananas over the cookies.

Spread half of the creamy topping mixture evenly over the bananas.

Repeat the layers: another layer of approximately 16 Chessmen cookies, followed by the remaining sliced bananas, and then the rest of the creamy topping.

For garnish, you can crush a few additional Chessmen cookies and sprinkle them over the top, or arrange whole cookies decoratively.

Cover the dish tightly with plastic wrap and refrigerate for at least 4 hours, or preferably overnight, to allow the flavors to meld and the cookies to soften.


In a large bowl, prepare the Jell-O Vanilla Instant Pudding according to package directions, using 3 cups of cold milk. Whisk until well combined and slightly thickened. Set aside.

In a separate large bowl, beat the softened cream cheese until smooth and creamy. Gradually add the entire can of sweetened condensed milk, beating until fully incorporated and the mixture is light and fluffy.

Gently fold in the thawed Cool Whip into the cream cheese and condensed milk mixture until no streaks remain. Be careful not to overmix.

Combine the prepared vanilla pudding with the cream cheese and Cool Whip mixture. Mix gently until just combined. This will be your creamy topping.

To assemble the pudding, arrange approximately 16 Pepperidge Farm Chessmen Butter Cookies in a single layer at the bottom of a 9x13 inch dish.

Layer half of the sliced bananas over the cookies.

Spread half of the creamy topping mixture evenly over the bananas.

Repeat the layers: another layer of approximately 16 Chessmen cookies, followed by the remaining sliced bananas, and then the rest of the creamy topping.

For garnish, you can crush a few additional Chessmen cookies and sprinkle them over the top, or arrange whole cookies decoratively.

Cover the dish tightly with plastic wrap and refrigerate for at least 4 hours, or preferably overnight, to allow the flavors to meld and the cookies to soften.
