Heat 2 tablespoons olive oil in a large pot over medium-high heat. Brown the ground beef, breaking it up with a fork, until cooked through, 7 to 8 minutes. Season the beef with 1/2 teaspoon each salt and pepper. Using a slotted spoon, transfer the beef to a paper towel-lined plate.
Heat the remaining 1 tablespoon olive oil in the pot. Add the onion, bell pepper and garlic and saute until softened, about 5 minutes. Stir in the chili powder, oregano and cumin and cook for 1 minute.
Return the beef to the pot. Stir in the beans, tomatoes, tomato sauce, corn, 1 1/2 cups water and 2 teaspoons salt. Simmer 30 to 45 minutes. Taste and add more chili powder, if desired.
Ladle the chili into serving bowls and top with a dollop of sour cream and a sprinkling of cheddar cheese.
Photograph by Andrew McCaul
Recipe courtesy Bobby and Jamie Deen for Food Network Magazine