Preheat the oven to 400ºF. Cut the top quarter off the head of garlic, drizzle the bulb with olive oil, and wrap tightly in a square of aluminum foil. Place in the oven on the middle rack and bake 50 minutes or until soft and brown.

Meanwhile, place tomatoes on a rimmed baking sheet, drizzle with 1 tablespoon olive oil, and season with salt and pepper. Place in the oven and bake 40 minutes, stirring once or twice to make sure they don’t burn.

While the tomatoes and garlic are roasting, bring a large pot of water to a boil and cook the penne according to package directions, reserving ½ cup cooking water just before draining. Return the pasta to the pot.

Once the tomatoes and garlic are done, remove from the oven and mash the tomatoes with a fork. Squeeze the garlic out into the tomatoes, add another tablespoon of olive oil, and mash it all together with the fork. Add the tomato sauce to the pasta along with a splash of the reserved cooking liquid and stir to coat completely. You can add more pasta water or olive oil if you prefer to loosen the sauce up a bit. Add the basil and stir one more time, then serve topped with Parmesan cheese.