Pour one package of Island Pineapple Jello into a mixing bowl.
Bring water in a kettle to a boil.
Add 1 cup boiling water to the pineapple jello and stir until the crystals dissolve.
Add ½ cup white rum and ½ cup cold water. Together, the rum and cold water should equal 1 cup of liquid.
Pour the mixture into the bottom third of 36 jello shot cups. Refrigerate for 2 to 4 hours, until set.
Mix the coconut cream pudding, ¼ cup Malibu coconut rum, and 1¾ cups cold milk until thick. More rum can keep the pudding from setting, so do not increase it.
Spoon the pudding over the set pineapple layer and chill until firm.
Prepare the second pineapple layer with the remaining jello, 1 cup boiling water, ½ cup white rum, and ½ cup cold water.
Let the new jello mixture cool completely. Spoon it gently over the pudding so the liquid does not melt the middle layer.
Refrigerate for another 2 to 4 hours. Add a little Cool Whip before serving if desired.