Make the crust: Pulse 1 box of Nilla Wafers in a food processor until fine. Mix in ¼ cup brown sugar and 1½ sticks melted butter. Press the mixture into the bottom of a 13x9 dish and refrigerate for 10 minutes.
Cheesecake layer: Spread the no-bake cheesecake filling evenly over the chilled crust.
Pudding layer: In a bowl, whisk together the pudding mixes and cold milk. (Add rum extract if using.) Mix until thick and set aside.
Banana layer: Slice bananas and lay them over the cheesecake layer.
Add the pudding: Pour the pudding over the bananas and gently spread it out.
Top with Cool Whip: Spread a layer of Cool Whip on top.
Chill: Refrigerate for at least 1 hour, or until set.
Serve: Right before serving, add more banana slices, Nilla Wafers, and a drizzle of caramel on top.
