Preheat the oven to 350°F (175°C). Lightly grease a 12-cup muffin pan.
Beat the softened butter, granulated sugar, and brown sugar until light and creamy.
Add the egg and vanilla extract. Mix until well combined.
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the butter mixture, mixing just until combined.
Fold in the crushed vanilla wafers.
Divide the dough evenly between the muffin cups. Press the dough into the bottoms and slightly up the sides.
Bake for 10 to 13 minutes, until the edges are lightly golden and the centers are still slightly soft.
Remove from the oven. While the cookies are warm, gently press the centers with the back of a small spoon to create cup-shaped wells.
Cool the cookie cups in the pan for 5 to 10 minutes, then transfer them to a wire rack and cool completely.
Whisk the banana cream pudding mix with the cold milk until thickened.
In another bowl, beat the softened cream cheese, powdered sugar, and vanilla until smooth.
Combine the cream cheese mixture with the pudding mixture. Gently fold in the whipped topping until smooth and fluffy.
Spoon or pipe the banana cream filling into the cooled cookie cups.
Top each cookie cup with fresh banana slices and a swirl of whipped cream.
Sprinkle with crushed vanilla wafers and refrigerate for at least 30 minutes before serving.