In large skillet, cook beef until browned and cooked through, breaking it up with a wooden spoon as you go.
Remove from skillet and place on plate lined with a paper towel. Set aside.
Heat oil in same large skillet over medium heat.
Add onion and cook until it begins to soften, about 4-5 minutes.
Add bell pepper and cook another 4-5 minutes, until pepper softens.
Add beef back to skillet, along with beans, tomatoes, chili powder, cumin, paprika, and cayenne pepper. Bring to a boil.
Reduce heat to maintain a simmer, cover and cook until slightly thickened, about 20 minutes.
Meanwhile, preheat oven to 350 degrees F. Spray a 3-quart baking dish with cooking spray. Set aside.
To make the cornbread: whisk together the cornmeal, flour, sugar, baking powder, baking soda, and salt until well combined.
In separate small bowl, whisk together egg, milk, and oil.
Add wet ingredients to dry ingredients and stir until just combined.
When chili is done cooking, transfer to prepared baking dish. Top with cheese then spread cornbread batter over chili.
Bake in preheated oven 25-30 minutes, until cornbread is cooked through.
Let sit for 10 minutes before serving