In a mixing bowl, whisk together cold milk and pudding mix until smooth and thickened.
In a separate bowl, whip the cream until soft peaks form (skip if using whipped topping).
Gently fold the whipped cream into the pudding mixture.
In serving cups, add a layer of cookies at the bottom.
Add a layer of sliced bananas on top of the cookies.
Spoon a layer of pudding mixture over the bananas.
Repeat the layers until the cups are filled.
Finish with extra whipped cream or crushed cookies on top if desired.
Chill in the refrigerator for at least 1–2 hours before serving.