Combine pudding, cream cheese, sweetened condensed milk, whip cream, rum extract and white sugar in a bowl.
In a cast iron pan over the flame broiler, combine butter, brown sugar and cinnamon. Stir constantly until bubbles form. Chop 8-10 bananas into the sugar mixture. Remove from heat immediately.
Layer nilla wafers, bananas then cream in mason jars. Repeat order until the jar is full. Sprinkle with cinnamon and either serve or let sit in the fridge for up to 24 hours before serving. The longer it sits the softer the wafers will become.