Preheat oven to 350 degrees F (175 degrees C). Place mushrooms in a baking dish.
Cook and stir tomatoes, balsamic vinegar, olive oil, basil, garlic, parsley, and red pepper flakes in a large skillet over medium heat until heated through, 5 to 10 minutes.
Top each mushroom with 1/2 of the tomato mixture. Sprinkle pepperjack cheese and mozzarella cheese on top of tomato mixture; top with black olives and bread crumbs.
Bake in the preheated oven until golden brown and crispy, about 25 minutes.
