Preheat oven to 400 degrees F (200 degrees C).
Wash and scrub the Potato (2), then prick all over several times with a fork. Rub each potato with Vegetable Oil (1/2 tablespoon).
Place in a cast iron skillet and bake for approximately 45 minutes to 1 hour, until potatoes are cooked through. Check doneness by running a small knife through the center.
When potatoes are done, cut a large wedge into each potato. Carefully scoop out the insides, leaving a "potato bowl." Reserve potato insides for another use.
Reduce oven heat to 350 degrees F (180 degrees C).
Remove potatoes from the skillet. Heat stove to medium high. Melt Butter (2 tablespoon) and add Onion (1) and Bell Pepper (1). Stir and cook for 10 minutes.
Add Brown Sugar (1/2 tablespoon) and Worcestershire Sauce (1/2 teaspoon), then stir and cook an additional 5 minutes until vegetables are tender.
Move the onion and pepper mixture to the sides of the skillet. Return potatoes to the skillet. Fill each with Chili Pepper (1 1/2 cup).
Top each chili potato evenly with onions and peppers, then with the Sharp Cheddar Cheese (1 cup).
Return the skillet to the oven for 20-25 minutes, until the chili is warmed through and the cheese is melted, golden brown, and bubbly.
Transfer to a plate and serve warm. Enjoy!