Prepare crust according to recipe directions. Chill until filling is ready. (You can also use a store bought crust.)
Place 2/3 cup sugar, cornstarch, and salt in a medium saucepan. Whisk in milk. Place over medium-low heat and stir constantly with a wooden spoon until the mixture thickens and just starts to boil, about 5-7 minutes. Remove from heat and stir in 1 tablespoon vanilla bean paste (or extract). Transfer to a heat safe bowl and cool to room temperature, then chill for at least 4 hours.
Make the whipped cream: beat remaining 1/4 cup granulated sugar with the cream cheese until smooth, scraping the sides of the mixing bowl often. Slowly add the heavy whipping cream and 1 teaspoon vanilla and beat on high speed until stiff peaks form. This will take a minute or two in a stand mixer, longer time with a hand mixer.
Fold 3/4 cup of the whipped cream into the pudding.
Slice the bananas. Place a single layer of sliced banana in the bottom of the prepared crust. Top with half the pudding, then another layer of bananas, then another layer of pudding. Top with remaining whipped cream, a banana slice and crumbled cookies. Chill at least 1-2 hours before serving.
This pie is best assembled and eaten the same day. The pudding and crust can be made the day before, but don’t make and assemble the whipped cream and pie until the day it’s to be served. Store in refrigerator.