Brush 1 tablespoon of olive oil over the bottom of a 12" cast iron skillet (or if you don't have a cast iron skillet, spray a large casserole dish with vegetable spray) and set aside.
Lay the cornbread in a single layer on a baking sheet and bake for 10 minutes. Turn cornbread with a spatula and bake another 10 minutes until browned and crisp. Set cornbread aside to cool and turn up the oven to 375 degrees.
Heat a large skillet over medium high heat. When the pan is hot, add the chopped bacon and cook until browned and crisp. Transfer the bacon to a dish lined with a paper towel and set aside. Discard all but 1 tablespoon of the bacon fat. Add 1 tablespoon olive oil to the bacon fat and stir in the chopped onion, celery and bell pepper. Saute until tender and translucent, about 5 minutes. Add the chopped chili peppers, ancho chili powder and black pepper and stir to combine.
Add the cornbread and gently toss with the vegetables. Add the chopped bacon, corn, parsley and cilantro. Drizzle the chicken broth an half and half over the mixture and toss very gently until liquids are combined and absorbed.
Transfer the stuffing to the cast iron skillet or casserole and bake for 25-30 minutes until browned and crispy. Serve.