Preheat the oven to 375 degrees and lightly grease a loaf pan.
In a large bowl, combine the ground beef, breadcrumbs, egg, onion, garlic, bourbon, ketchup, Worcestershire sauce, smoked paprika, and cayenne pepper. Mix with your hands until just combined.
Transfer the mixture to the prepared loaf pan and press it into an even shape.
Bake for 45 minutes.
While the meatloaf bakes, stir together the brown sugar and apple cider vinegar in a small bowl to form the glaze.
Remove the meatloaf from the oven, spread the glaze evenly over the top, and return it to the oven for another 15 minutes.
Let the meatloaf rest for 10 minutes before slicing.