Chessmen Cookie Banana Pudding

I love butter cookies. When I hear the words, butter cookies, I instantly think of the blue tins that were always at my grandma’s house. Each paper cup had its own uniquely designed butter cookie. It was pure joy! Recently, I stumbled across a recipe for banana pudding with butter cookies.

One of my favorite things about this recipe besides the cookies, is that it DOES NOT have a banana candy flavor to it. I am not a fan of banana taffy and I have had tried many recipes that have that banana taffy flavor.

This is not the traditional vanilla wafer recipe we all grew up on. It’s way better!


5-6 medium bananas, sliced (my bananas were kind of small)

2 bags of Milano Chessman cookies

1 box of instant vanilla pudding

2 cups of milk

1- 8oz block of cream cheese, softened

1 can of sweetened condensed milk

Homemade Whipped Cream

1 tablespoon of vanilla

1 pint of whipping cream (Near the half and half in the dairy section. Homemade whipped cream is the best!)

Honey roasted pecans, optional

1. In a 9 x 13 dish, place the cookies down in an even layer and lay sliced bananas on top.

2. In a large mixing bowl, combine the instant vanilla pudding and milk. Beat with an electric mixer for two minutes. Set aside.

3. In a separate bowl, cream the sweetened condensed milk and cream cheese together. Set aside.

4. In a medium sized bowl, combine the vanilla and the whipping cream. Beat on low with an electric mixer until the liquid turns to whipped cream. It takes about 3-4 minutes. The whipped cream will have stiff peaks when it’s ready.

5. Fold the whipped cream into the cream cheese mixture. Then fold this into the pudding. Pour all of this over the bananas and cookies. Top with additional cookies in any pattern you like. Cover the dish and allow it to set in the fridge for a few hours before serving.

Optional: Top each serving with a little bit of chopped, honey roasted pecans. (My grandmother has a nut allergy so, we put the nuts on the side.)

Notes: Recipe has been slightly modified from Paula Deen’s Not Yo Mama’s Banana Pudding.

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