Preheat your oven to 400°F (200°C).
In a large bowl, combine the cherry tomatoes, sliced garlic, olive oil, dried oregano, red pepper flakes (if using), salt, and pepper. Toss gently to coat everything evenly.
Spread the tomato mixture in a single layer onto a large baking sheet. Roast for 20-25 minutes, or until the tomatoes have softened, burst, and started to caramelize. Give the pan a gentle shake halfway through roasting.
While the tomatoes are roasting, bring a large pot of salted water to a boil. Add the pasta and cook according to package directions until al dente.
Reserve about 1/2 cup of the pasta water before draining. Drain the pasta well.
Return the drained pasta to the pot. Add the roasted tomatoes and garlic mixture directly from the baking sheet, along with the chopped fresh basil and grated Parmesan cheese. Toss to combine.
If the sauce seems a little dry, add a splash of the reserved pasta water, a tablespoon at a time, until you reach your desired consistency. The starchy water helps to emulsify the sauce.
Serve immediately, garnished with extra Parmesan cheese and a drizzle of olive oil if desired.