Heavy bottomed skillet over medium high to high heat.
Arrange tomatoes on a broiler pan. Drizzle tomatoes with oil and season with salt and pepper. Combine bread crumbs, cheese, red pepper flakes, garlic, arugula and 1 tablespoon oil in food processor and pulse grind to form stuffing. Stuff tomatoes to the rims with arugula mixture and place in the center of the oven. Bake 10 to 12 minutes. Let tomatoes stand 5 minutes before serving.
Let steaks sit 10 minutes once removed from the refrigerator. Coat steaks liberally on both sides with coarse black pepper. To a very hot pan, drizzle oil to thinly coat the cooking surface. It will smoke. Add steaks immediately. Sear and seal the steaks, cooking them 4 minutes on each side. for medium rare doneness. Reduce heat a bit and cook 5 minutes longer for medium to medium well doneness. Remove steaks and let stand 5 minutes. Add brandy to the skillet and warm, then ignite. Add butter to the skillet, then spoon pan juices over steaks. Serve stuffed tomatoes along side steaks.