In a 10-inch skillet heat 2 teaspoons oil, add onion, red pepper, and garlic, and saute over medium-high heat until vegetables are tender, about 3 minutes. Add beans, tomatoes, olives, chili powder, and cilantro, and cook stirring frequently, about 3-5 minutes.
Spray four 16-ounce ovenproof ramekins with nonstick cooking spray; spoon ¼ of the bean filling into each ramekin, and set aside.
Make cornbread crust and assemble
Preheat oven to 400° F.
In a medium mixing bowl combine cornmeal, flour, and baking soda, and set aside. In a separate bowl, beat together with a whisk, the buttermilk, egg, 2 teaspoons oil, and a pinch of salt. Stir wet ingredients into the dry ingredients, mixing well. Pour ¼ of the cornmeal mixture over each portion of the bean filling, and bake for 15 to 20 minutes (until a knife inserted into the cornmeal mixture comes out clean).
Sprinkle each serving with ¼ of the shredded Cheddar cheese. Turn the oven to broil, and broil tamale pies until cheese is melted and lightly browned, 1 to 2 minutes. Serve hot, garnished with additional cilantro if desired.