Heat a large nonstick skillet over high heat. Season the steak with salt and pepper. Add 2 tablespoons extra-virgin olive oil to the pan. Brown 3 minutes on each side and remove. Add another turn of the pan extra-virgin olive oil and reduce heat to medium high. Add garlic, pepper flakes, mushrooms, onions, peppers and pepperoni, if using. Cook mixture 5 minutes, then add wine and scrape up any good-bits from the bottom of the skillet. Add tomatoes, oregano, salt and pepper, to taste. Slide steak back in and reduce heat to medium. Cover pan and cook 5 or 6 minutes for medium rare, 10 to 12 minutes for medium well. Remove meat, cut away from bone or divide into 2 large portions. Cover steaks with sauce and top with grated cheese.
Recipe courtesy of Rachael Ray