Preheat oven to 425°F.
In a large cast iron skillet, heat 2 tablespoons olive oil over medium heat.
Once oil is hot, add cherry tomatoes and garlic to the pan. Cook, stirring often until tomatoes and garlic are hot, about 2-3 minutes.
Place skillet in the preheated oven and bake until tomatoes are soft and garlic is roasted, about 10-15 minutes.
While tomatoes and garlic are in the oven, cook the spaghetti in a large pot of salted water until al dente. Drain and set aside.
Transfer skillet from the oven back to the stove. Use a potato masher to mash the tomatoes and garlic together making a chunky, rustic sauce.
Turn heat back on to medium and season sauce with salt and pepper.
Add the cooked pasta to the pan. Add a couple tablespoons olive oil and toss to coat the pasta with the sauce.
Stir in Shredded Parmesan cheese and stir until cheese melts.
Add some pasta water to the skillet if sauce is too dry.
Add chopped basil and toss to combine.
To serve, place pasta onto a plate and top with a glug of olive oil, freshly cracked black pepper, and a sprinkle of shredded Parmesan cheese.
Garnish with sprigs of basil if desired.