Ultimate Grilled Cheese Sandwich
['Butter', '4 slices country white sourdough bread, cut on deep diagonal into 1/3-inch-thick slices (each about 7x3 1/2 inches)', '4 thin slices prosciutto', '8 large fresh basil leaves', '8 (1/4-inch-thick) slices young Asiago cheese or drained fresh mozzarella cheese', '1/4 teaspoon dried crushed red pepper', '2 tablespoons olive oil', '6 (1/3-inch-thick) slices heirloom tomato (from about 1 large)']
Preheat oven to 400°F. Lightly butter 1 side of each bread slice. Place 2 bread slices, buttered side down, on work surface. Top each with 2 prosciutto slices, then 4 basil leaves, then 4 cheese slices. Sprinkle with salt and crushed red pepper. Top with remaining 2 bread slices, buttered side up. Heat olive oil in heavy large ovenproof skillet over medium-high heat. Add sandwiches to skillet and cook until golden on bottom, about 4 minutes. Turn sandwiches over; transfer skillet to oven and bake until golden and cheese melts, about 5 minutes. Remove from oven. Carefully lift off top bread slices from sandwiches and insert 3 tomato slices into each, then cover with bread tops and serve.
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