Whisk together 2 cups of cold milk and the instant pudding mix for about 2 minutes, then refrigerate for at least 30 minutes to set.

In a separate bowl, beat together the sweet condensed milk, softened cream cheese, and vanilla extract until smooth, then fold in Cool Whip.

Layer one-third of the whole vanilla wafers in a 9x13-inch dish, followed by half of the crushed cookies and one-third of the pudding mixture.

Add half of the banana slices over the pudding, then layer more whole wafers on top.

Repeat layering with more pudding, the remaining banana slices, and the rest of the crushed cookies, finishing with a layer of pudding.

Cover and refrigerate overnight to allow flavors to meld, ensuring the pudding is firm yet creamy when served.

Garnish with whole vanilla wafers, Chessman cookies, and a drizzle of caramel sauce before serving.