Preheat oven to 425 degrees F. Line a sheet pan with parchment paper.
Cut the package of bacon into thirds, so each slice will be three pieces.
Wrap each lil smokie in one third slice of bacon, and secure with a toothpick. You'll have some bacon leftover. Save for another use.
Place the bacon wrapped smokies on the parchment lined baking sheet in an even layer.
In a microwave safe bowl or measuring cup, melt the butter. Then stir in the brown sugar, bourbon, black pepper and cayenne pepper until smooth. Use a pastry brush to coat both sides of each bacon smokie with the butter and brown sugar mixture.
Bake the smokies for 15 minutes. Use tongs to carefully flip them over and cook for 15 minutes more, or until the bacon is nicely browned.