Cheese-Filled Meat Loaf
1 clove garlic, minced 1 cup shredded Cheddar cheese, or as needed 1 egg, beaten 1 pound ground beef 1 teaspoon ground black pepper 1 teaspoon salt 1 teaspoon Worcestershire sauce 8 slices bacon, divided ¼ cup brown sugar ¼ cup crushed pineapple, drained ¼ cup dry bread crumbs ⅓ cup ketchup