Preheat your oven to 350°F (175°C). In a medium bowl, combine the crushed vanilla wafer cookies and melted butter. Mix until the cookies are evenly coated.
Press the cookie mixture into the bottom of a 9x13 inch baking dish to form a crust. Bake for 10 minutes, then remove from the oven and let it cool completely.
In a large mixing bowl, whisk together the instant vanilla pudding mix and milk until smooth and thickened, about 2 minutes. Set aside.
In another bowl, beat the softened cream cheese, powdered sugar, and vanilla extract until creamy and well combined.
Gently fold half of the whipped topping into the cream cheese mixture until smooth. Then, fold in half of the prepared pudding mixture.
Spread half of the cream cheese mixture over the cooled cookie crust. Layer half of the sliced bananas on top.
Pour half of the remaining pudding over the bananas, followed by another layer of the cream cheese mixture and the rest of the bananas.
Top with the remaining pudding mixture and spread the rest of the whipped topping over the top. If desired, sprinkle with ground cinnamon.
Cover with plastic wrap and refrigerate for at least 4 hours, or overnight for best results, to allow the flavors to meld and the layers to set.