Chessmen Cookie Banana Pudding

White dish with banana pudding dessert inside of it with chessmen butter cookies, pudding, and sliced bananas.

Chessmen Cookie Banana Pudding is a layered dessert recipe with butter cookies, fresh sliced bananas, and a creamy & thick banana cream pudding + French vanilla pudding mixture with Cool Whip and sweetened condensed milk.

Course Dessert

Cuisine American

Keyword banana pudding with chessmen cookies recipe, chessmen banana pudding, chessmen cookie banana pudding

Prep Time 20

Cook Time 0

Fridge Time 6

Total Time 6 20

Servings

Calories 219kcal

Author Jessica - Together as Family

Ingredients

2 bags (7.25 oz each) Pepperidge Farm Chessmen Butter Cookies
4-5 bananas thinly sliced
2 cups half and half
1 box (3.4 oz) banana cream instant pudding
1 box (3.4 oz) french vanilla instant pudding
8 ounces cream cheese softened
1 can (14 oz) sweetened condensed milk
1 tub (8 oz) Cool Whip thawed

Instructions

In a 9x13 baking dish layer 24 cookies into the bottom.
* Use any of the broken cookies from the two packs for the bottom layer. You want to do 4 columns with 6 cookies in each. You may have to cut some towards the bottom depending on the pan shape.
Layer the sliced bananas over the cookies. You will have enough to overlap some of the bananas, which is fine.
In a mixing bowl, add the half & half, banana cream instant pudding, and french vanilla instant pudding. Beat with a hand mixer until it’s combined well. Mixture will be thick. Let it sit while you prepare the next step so it can thicken up more.
In a separate bowl, add the cream cheese and sweetened condensed milk. Beat with a hand mixer until combined and creamy. Fold the Cool Whip in and stir until it’s mixed well.
Add the pudding mixture into the cream cheese mixture and stir with a wooden spoon until it’s combined well. Pour this over the sliced bananas and spread it out evenly.
Place the remaining 24 cookies over top in the same pattern as the bottom layer. 4 columns with 6 cookies in each. Cover the pan with plastic wrap and refrigerate for at least 6-8 hours before cutting and serving.
When ready to serve, cut the banana pudding using the cookies as the reference point. One cookie square area will equal one serving of the dessert.

Video

Notes

Instant Pudding : The original version of this recipes calls for two boxes of vanilla pudding. I really like the combo of french vanilla + banana cream so that is what I use. If you can't find french vanilla, then plain vanilla works great too.

Half and Half : This is a lighter version of heavy cream and can be found by the other milks at the store. You want the fat in this milk that will help create a thick and set texture, which makes this dessert easier to cut into squares. I do not recommend substituting this with anything else. You could get away with using whole milk.

Make It Ahead of Time : Plan ahead because this dessert needs to be in the fridge for at least 6-8 hours before serving and cutting. You can even make it the day before and let it refrigerate for up to 12 hours before serving. Because you have not cut into it yet, the bananas will not brown at all!

Once you cut into the dessert, the exposed banana layers will turn brown, which it will look ugly but it still tastes delicious. You can also go into the not exposed squares to eat leftovers because the bananas will not be browned yet.

Leftovers : Store leftovers in the pan, covered, for up to 4-5 days. Leftovers were amazing on day 3 and 4. The cookies do get softer the longer it's in the fridge.

Nutrition