1 pint Heavy Whipping Cream
1/4 cup Sugar
1/4 teaspoon Vanilla Powder or 1 teaspoon Vanilla
1 8oz block Cream Cheese
1 14oz can Sweetened Condensed Milk
1 3.4oz box Instant Vanilla Pudding Mix
1 cup Half and Half, you can sub regular milk
4 ripe Bananas
2 Packages Chessman Butter cookies
In a stand mixer beat whipping cream, sugar and vanilla powder until thick. Beat on medium speed rather than high speed to stabilize the cream. This will take longer, but will ensure the cream is not weepy.
Remove 1/2 of the whipped cream to a separate bowl.
Add cream cheese to the stand mixer and whip until combined with cream.
Add can of condensed milk. Whip until combined.
Add vanilla pudding powder. Whip until combined.
Add half and half. Whip until combined, smooth and thick.
Arrange the cookies from one package into the bottom of 1- 9"x 13" rectangular or 2 - 8"-9" square cake pans. Do not overlap cookies.
Spoon over the top of cookies 1/2 of the cream mixture. Spread evenly.
Slice two of the bananas over the top of the cream mixture.
Spoon over the top of the bananas the reserved whipped cream. Spread evenly.
Slice remaining two bananas over the top of the whipped cream.
Spoon remaining cream mixture over the top of the whipped cream. Spread evenly.
Top cream mixture with remaining cookies, arranged in the same direction as was done on the bottom of the pan. This ensures clean cuts and serving of portions.
Gently press cookies into the cream, cover and refrigerate for at least 2 hours. I prefer to refrigerate overnight to soften the cookies slightly.
Serve by cutting along cookie edges and lifting out of the pan.
Makes 12-24 servings, depending on cutting along 1 or two cookies. 1 cookie portion photographed below.