Crust: Blend or with a rolling pin crush about 20 Oreo's. Melt the butter and mix in to the crushed cookies. Pour in to an 8x8 baking dish to create a crust. Place in freezer for a minimum of 30 minutes.
In a bowl, combine the instant banana pudding with the milk. Set aside.
With an electric mixer, combine 1 mashed banana and cream cheese and mix until creamy. Stir in vanilla and powdered sugar. Gently fold in 1 cup of cool whip.
Remove the crust from the freezer, create a single layer with all the sliced bananas.
Pour the mix from step 3 over the layer of bananas and spread evenly. Next, pour the pudding from step 2 over and spread evenly. Top with a layer of cool whip.
Let it chill in the fridge for 2 - 3 hours. Top with a few broken or crushed Oreo's and sliced banana. Enjoy!