Preheat the oven to 400 degrees F (200 degrees C).
Place tomato halves snugly side by side in a shallow baking dish. Insert whole cloves of garlic between tomatoes. Brush olive oil over the top and sprinkle with basil. Season with salt and pepper.
Bake uncovered in the preheated oven until tomatoes have softened and are sizzling in the pan with the edges slightly charred, 35 to 45 minutes. Serve hot.
