In a large skillet, cook the ground beef and onion over medium heat until the beef is browned and the onion is softened.
Drain any excess fat. Stir in ketchup, brown sugar, Worcestershire sauce, and bourbon.
Preheat the broiler.
Simmer for 10–15 minutes, until the mixture has thickened. Season with salt and pepper to taste.
Meanwhile, dice bacon and cook to desired doneness.
Toast the hamburger buns under the broiler until golden brown.
Divide the sloppy joe mixture evenly among the bottom halves of the buns. Top each with shredded cheddar cheese and crumbled bacon. Place the top halves of the buns on top.
Return the assembled sandwiches to the broiler and broil until the cheese is melted and bubbly.