Step 1

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.

Step 2

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.

Step 3

Gently fold in the Cool Whip, using a rubber spatula, just until combined.

Step 4

Transfer to the bowl with the pudding and stir gently until completely combined.

Step 5

Line the bottom of a 9x13-inch casserole dish with 1 bag of the cookies.

Step 6

Top with sliced bananas in an even layer.

Step 7

Next, top the bananas with the whipped cream mixture and smooth out even with a rubber spatula.

Step 8

Lastly, lay out the second bag of Chessmen cookies.

Step 9

Cover dish with plastic wrap and refrigerate at least 3 hours (overnight is even better!)

Step 10

Scoop the banana pudding onto serving plates and enjoy!