In a bowl combine the cream cheese, condensed milk, box of pudding, milk and vanilla extract. Mix with a hand mixer until combined and smooth. Let sit for 5 minutes until slightly firm. Then add in half of the container of cool whip and fold in.
In a bowl or pie plate, cover the bottom with the cookies. Pour 1/3 or 1/2 (this depends on how deep you’re pie dish or bowl is) on top and smooth over. Cover with banana slices and crumble a few cookies and add on top. Repeat with the pudding, banana slices and cookie crumbles. Add the remaining cool whip on top, smooth over, top with banana slices and cookie crumbles.
Let chill in the fridge for 3-4 hours.