To make bread pudding: Tear rolls into 1/2-inch square pieces, being careful not to squeeze bread so it remains light and fluffy. Place bread in a bowl. Add milk and, stirring occasionally, let bread absorb milk to point of saturation, about 15 minutes.
In another bowl, beat eggs. Add sugar, vanilla, raisins, and pineapple. Mix well. Add to bread/milk mixture and mix until combined with a rubber spatula. Preheat oven to 375 degrees.
Pour into 13x9-inch or 14x10-inch pan. There should be about 1-inch headspace. Loosely cover the pan with foil. Bake in preheated oven 40 to 45 minutes or until golden brown and puffy. While pudding is cooking, do not slam oven door. Check for doneness by piercing pudding in several places with a toothpick. Each time toothpick should come out clean.
Cool slightly, cut into 6 portions. Top each with warm Jack Daniels sauce. Makes 6 servings. Sauce Directions Place water and sugar in a saucepan. Mix until sugar dissolves. Set over medium heat and cook without stirring until mixture comes to boil. Immediately reduce to simmer and cook until mixture is clear. Turn off heat.
Add butter, stir until butter is completely melted. Add cinnamon, lemon juice, vanilla and Jack Daniels; whip lightly to combine. Remove from stove top and cool slightly. Serve immediately or cool completely and reheat when ready to serve.