Preheat oven to 450° F.
Add fresh tomatoes and fresh basil to a small cast iron skillet (or baking sheet). Drizzle generously with half of the extra virgin olive oil (about 2 tablespoons) and salt and black pepper and stir until tomatoes are evenly coated. Set aside.
Slice 1/4 inch or so off the top of the garlic bulb to reveal cloves.
Create a spot for the garlic bulb by moving some tomatoes aside. Place cut side up. Drizzle the top with olive oil, season with salt and pepper.
Place in preheated oven and roast for 30-35 minutes or until tomatoes are browned and bursting.
Bring a large pot of water to a rolling boil. Salt the water generously and add pasta to the pot, stirring for about 30 seconds to ensure no noodles stick together. Cook pasta according to al dente package directions on box. Drain and add back to pot.
BEFORE draining the pasta, reserve about 1/2 cup to 1 cup of the pasta water. Drain and add spaghetti noodles back to the pot.
To the pot, add the roasted tomatoes and basil (along with the pan juices) and squeeze out the roasted garlic cloves, discarding the garlic paper. Add the remainder of the extra-virgin olive oil and parmesan cheese. Add the pasta water as needed to loosen up the sauce. Season with italian seasoning, and more salt and pepper to taste (if needed). Stir until well combined.
Serve hot with additional parmesan cheese and garnish with chiffonade basil. Enjoy!