Crisp the bacon: Add chopped bacon to a large pot or Dutch oven over medium heat. Cook until crisp, 6–8 minutes.
Remove with a slotted spoon and set aside, leaving about 2 tablespoons bacon fat in the pot.
Brown the beef: Add ground beef to the pot. Cook, breaking it up, until browned and no longer pink, 6–8 minutes. Drain excess grease if needed, but leave a thin layer for flavor.
Sauté the aromatics: Stir in onion, bell pepper, and jalapeño.
Cook until softened, 4–5 minutes. Add garlic and cook 30 seconds until fragrant.
Build the base: Add tomato paste and cook, stirring, 1 minute to caramelize. Sprinkle in chili powder, smoked paprika, cumin, oregano, salt, and black pepper.
Simmer: Pour in diced tomatoes with juices, beef broth, and Worcestershire (if using).
Return bacon to the pot. Bring to a gentle simmer, reduce heat to low, and cook uncovered 15–20 minutes, stirring occasionally, until slightly thickened.
Add the “cheeseburger” touch: Stir in mustard (if using), heavy cream, and cream cheese until smooth. Reduce heat to low and fold in 1 cup shredded cheddar until melted and silky.
Taste and adjust: Add more salt, pepper, or chili powder to your liking.
If you prefer a looser chili, splash in a bit more broth.
Serve: Ladle into bowls and top with remaining 1/2 cup cheddar, scallions, and a spoon of no-sugar pickle relish if you like that classic burger finish.