01 - Heat olive oil in a large pot over medium heat. Add ground beef and cook until browned, breaking it up with a spoon, about 5-7 minutes.
02 - Add onion and bell pepper; sauté for 5 minutes until softened. Stir in garlic and cook for 1 minute more.
03 - Sprinkle in chili powder, cumin, smoked paprika, oregano, and cayenne. Stir to coat the meat and vegetables evenly.
04 - Add crushed tomatoes, diced tomatoes, kidney beans, black beans, beef broth, salt, pepper, and brown sugar. Stir to combine, bring to a gentle boil, then reduce heat and simmer uncovered for 45 minutes, stirring occasionally, until thickened and flavors meld. Adjust seasoning to taste.
05 - Preheat oven to 400°F. Grease an 8-inch square baking dish with butter or cooking spray.
06 - In a large bowl, whisk together cornmeal, flour, sugar, baking powder, and salt until well combined.
07 - In another bowl, whisk milk, eggs, melted butter, and oil until smooth.
08 - Pour wet ingredients into dry ingredients; stir until just combined. Do not overmix.
09 - Spread batter evenly in the prepared dish. Bake for 20-25 minutes, or until golden and a toothpick inserted in the center comes out clean. Cool slightly before slicing.
10 - Ladle chili into bowls and serve with warm cornbread on the side.