Chessmen Cookies Banana Pudding

Our spin on a widely popular Banana Pudding, with a few twists and additions. The chessmen cookies still bring that elegant presentation, but with all the delectable flavor and no baking required!
Prep Time: 15 minutes
Chill Time: 4 hours
Total Time: 4 hours 15 minutes
Course: Dairy, Dessert, Snack
Cuisine: American
Keyword: banana pudding with pepperidge farm chessmen cookies, chessmen cookies banana pudding, not yo mamas banana pudding, pepperidge farm chessman cookie banana pudding
Servings: 12 servings


  • 1 KitchenAid Mixer paddle attachment
  • 1 13 x 9 baking pan


  • 2 pkgs Pepperidge Farm Chessmen cookies good ole fashioned vanilla wafers, butter cookies or shortbread cookies work too
  • 3 - 6 medium bananas sliced; depending on how much you like bananas will determine how many you choose to use
  • 1 8 oz pkg Cream Cheese Blocks softened to room temperature
  • 1 14 oz can sweetened condensed milk
  • 1 tsp Madagascar vanilla bean extract
  • 1 5 oz box Instant Banana cream pudding mix french vanilla or vanilla pudding mix can be used too
  • 2 cups whole milk any milk will do
  • 12 oz Cool Whip thawed


  • Line the bottom of your 13 x 9 baking pan with one package of cookies. Top with the sliced bananas.
  • In the stand mixer, beat the cream cheese with sweetened condensed milk and vanilla extract until smooth. Add in pudding mix and milk. Beat for about 5 minutes, scraping down the sides of the bowl as needed.
  • Fold in the cool whip and spread over banana layer.
  • Top with the remaining package of cookies. Cover with plastic wrap and refrigerate for 4 hours. Enjoy!!
    NOTE: For best results, although it's difficult due to the temptation, allow to chill for at least 4 hours, but overnight is absolute best as it firms up!
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