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1
In a bowl, combine very cold milk with instant vanilla pudding mix. To keep the milk cold, add an ice cube to the measuring cup. Whisk together thoroughly.
2
Let the pudding mixture sit for about 5 minutes to thicken. While waiting, prepare your Chessman cookies and Nilla Wafers by having them ready for assembly.
3
Once the pudding has thickened, stir in the sweetened condensed milk.
4
Gently fold in the Cool Whip with a whisk, trying to be as gentle as possible to maintain the fluffy texture. You can also use freshly whipped heavy cream as a substitute.
5
Spread a thin layer of the cream mixture on the bottom of a 9 by 13-inch baking dish to act as a base.
6
Create the first cookie layer with about six Chessman cookies, then fill in the gaps with Nilla Wafers, breaking them as needed.
7
Layer banana slices on top of the cookies, using about one to one and a half bananas, avoiding the edges to ensure the cream mixture covers them well.
8
Spread about one-third of the cream mixture over the bananas and smooth it out.
9
Repeat the layering process: alternate between cookie and banana layers, then cream mixture. Build three complete layers of cookies and bananas with three layers of cream in between, finishing with cookies on top.
10
Top with Chessman cookies, then before serving, sprinkle with crushed Nilla Wafers to maintain freshness and crunch. Cover loosely and refrigerate for a minimum of 4 hours, preferably 6 hours or overnight. Do not refrigerate longer than overnight, as the bananas will oxidize.
11
When ready to serve, gently scoop and plate the pudding. It will have a nice texture and hold together beautifully.
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