This recipe has been in my family for years and years. I remember sitting with my great grandma trying to get her to help me write everything down. The house smells of cinnamon and whiskey. What could be better??
BEFORE YOU BEGIN (OPTIONAL): Lay out bread slices and allow to get a crusty as possible (I will usually set out at least 24 hours in advance.) This allows the bread to become very dry and crusty so it can absorb as much pudding as possible. ALSO combine the raisins and whiskey in a small bowl, cover, and place in the refrigerator overnight to allow the raisins to soak up as much whiskey as possible. If you forget, the raisins only need to sit for about 30 minutes to soak up quite a bit of whiskey.
JACK DANIEL'S CARAMEL-WHISKEY SAUCE: Combine sugar and water in a small saucepan over medium-high heat. Stir continuously until sugar dissolves.
Simmer until sugar mixture is golden (about 17 minutes). DO NOT STIR!
Remove from heat.
Carefully add butter and cream cheese, stirring constantly with a whisk until all clumps are dissolved. CAUTION! Mixture will bubble vigorously and release a lot of hot steam.
Cool slightly. Stir in whiskey and milk. Mixture will bubble a bit at this step as well.
PUDDING: Preheat oven to 350°F.
Brush melted butter on one side of French bread slices.
Bake buttered side up until lightly toasted, about 10 minutes.
Cut bread into 1/2 inch cubes and set aside.
Combine milk, sugar, vanilla extract, evaporated milk, eggs, and UNDRAINED whiskey mixture in a large bowl. Stir well with a whisk.
Add bread cubes, pressing down gently to moisten; let stand about 20 minutes. If your bowl is a little small, gently fold the cubes into the mixture with a spatula.
Pour bread mixture into a 13 x 9-inch baking dish coated well with cooking spray.
Combine sugar and cinnamon; sprinkle over pudding.
Bake at 350F for 35 minutes or until set.
Serve warm with Jack Daniel's caramel-whiskey sauce.
TO MAKE THIS KID FRIENDLY: Substitute apple juice for Jack Daniel's in pudding and 1 tablespoon imitation rum extract and 3 tablespoons water in Caramel-Whiskey sauce.