Whip 1 cup of cold milk, vanilla and 2 packets of Dream Whip in a large bowl on high speed until thick and soft peaks form.

Combine Dream Whip mixture with chocolate pudding using a spatula or a hand mixer until combined. Try not to over mix as it may start to deflate the mixture.

In another bowl, combine heavy whipping cream, vanilla and powdered sugar. Whip on high speed with a hand mixer until soft peaks form.

Crush cookies in a plastic bag or in a food processor.

In a large bowl, glass trifle bowl or individual glasses- begin with the pudding layer and alternate with whipped cream. Sprinkle some of the crushed cookies in between layers if you wish, or leave them just for the topping. Refrigerate covered for at least 4 hours, preferably overnight. You can reserve the crushed cookies for the topping until ready to serve if you’d like.