Preheat the oven to 350 degrees F (175 degrees C). Grease a 9x13-inch baking dish.
Heat a large skillet over medium-high heat. Cook and stir ground beef, onion, and bell pepper in the hot skillet until beef is browned and crumbly, 5 to 7 minutes. Drain and discard grease.
Stir tomatoes, tomato sauce, corn, olives, chili powder, garlic, cumin, salt, red pepper flakes, and black pepper into the skillet. Bring to a low boil, about 5 minutes. Reduce heat to medium-low and let simmer for 5 minutes. Stir in 1 cup Cheddar cheese and continue to simmer until melted, 3 to 5 minutes. Remove from heat and transfer mixture to the prepared baking dish.
Heat milk, butter, sugar, and salt for topping in a large saucepan over medium heat until butter has melted, 2 to 3 minutes. Reduce heat to low and stir in cornmeal a little at a time, stirring vigorously with each addition, until smooth and thickened. Remove from heat and stir in 1 cup Cheddar cheese. Drizzle in beaten eggs slowly, stirring vigorously until combined. Pour mixture over filling in the prepared dish, smoothing evenly over the surface.
Bake in the preheated oven until top is golden brown and filling is bubbly, 30 to 40 minutes. Allow pie to rest for 10 to 15 minutes before serving.
