"Uncle Lucky and Aunt Bert's fruitcake cookies are a Virginian Christmas tradition. The cookies will soften and the flavour will mature when stored. The longer the cookies sit, the more the flavour will develop. They also freeze well."
Place raisins, candied cherries, dates, and candied pineapple in a bowl; stir in 1/2 cup bourbon whiskey; set aside to soak.
Beat butter and brown sugar together in a large bowl with an electric mixer until light and fluffy. Beat one egg at a time into the butter mixture; beat in vanilla extract and cinnamon with last egg.
Stir pecans and fruit mixture into butter mixture; stir in self-rising flour alternately with remaining bourbon whiskey as needed to form a soft dough. Drop tablespoonfuls of dough 2 inches apart onto ungreased baking sheets.
Bake in the preheated oven just until cookies begin to look dry, about 30 minutes. Cool cookies on a wire rack; store in a sealed container lined with waxed paper.