- In a large mixing bowl, using electric hand mixer, combine milk and instant pudding mix. Mix on low speed until combined and thickened, about two minutes.
- In a separate large mixing bowl, combine softened cream cheese and sweetened condensed milk. Beat together on medium-high speed until no lumps remains and mixture is smooth.
- Gently fold in the Cool Whip, using a rubber spatula, just until combined.
- Transfer to the bowl with the pudding and stir gently until completely combined.
- Line the bottom of a 9×13-inch casserole dish with 1 bag of the cookies.
- Top with sliced bananas in an even layer.
- Next, top the bananas with the whipped cream mixture and smooth out even with a rubber spatula.
- Lastly, lay out the second bag of Chessmen cookies.
- Cover dish with plastic wrap and refrigerate at least 3 hours (overnight is even better!)
- Scoop the banana pudding onto serving plates and enjoy!
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