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Southern Chessman Banana Pudding

Southern Chessman Banana Pudding (Alice Anderson)



2 cups cold milk

2 (3.4 ounce) packages instant French vanilla pudding mix (or 1 and 1/2 batch cooked vanilla custard) 

1 (14 ounce) can sweetened condensed milk

1 (8 ounce) package cream cheese, softened

1 (8 ounce) container whipped topping (such as Cool Whip), thawed in fridge

2 (7.25 ounce) packages butter shortbread cookies (such as Pepperidge Farm Chessmen)

6 medium/large bananas, sliced thin


1. Take all of your cookies out of their bags/slips. Sort any broken cookies to use for base 

2. Slice 6 bananas, fairly thin

3. Place even rows on the cookies at the base of a 9x13 pan 

4. Layer banana slices evenly over the shortbread (thinner slices should overlap to completely cover the cookies) 

5. In a medium bowl, combine milk with vanilla pudding packets, whisk vigorously until there are no lumps, set aside

6. In a large bowl, use an electric mixer to combine cream cheese and sweetened condensed milk until smooth 

7. Fold in the whipped topping until smooth

8. Fold in pudding until smooth

9. Pour pudding picture over the shortbread and bananas, smoothing until even 

10. Arrange final layer of shortbread across the top—for best results do not crowd the cookies—you want them to line up with the bottom layer of cookies, making it easier to slice later (slices beautifully). Push them into the pudding mixture just slightly. 

11. Put in the fridge 3 hours to overnight. 

12. Refrigerate after serving 


Note: You will be tempted to use banana pudding—don’t! The fresh bananas do the job!

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