Preparation

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!