In a small pot, bring water to a boil. Add the jello and stir till dissolved. Set aside for 15 minutes to cool.
In a mixing bowl, whisk together the milk and pudding mix till it begins to thicken.
Add 1/2 cup of rum and whisk till smooth. Place in fridge while you finish preparing the jello layer.
Add 1/2 cup rum to the jello and whisk to evenly mixed.
Fill the shot cups 1/3-1/2 full of jello mixture. Place shots on a cookie sheet and put them in the fridge until jello is set.
When jello is set, spread the pudding over the jello layer.
Garnish with whipped cream and crushed graham crackers.