Preheat your oven to 400°F (200°C).
On a large baking sheet, toss the cherry tomatoes and sliced garlic with 1/4 cup of olive oil, dried oregano, red pepper flakes (if using), salt, and pepper. Spread them out in a single layer.
Roast for 20-25 minutes, or until the tomatoes have burst and are slightly caramelized, and the garlic is fragrant and lightly golden.
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 cooking water before draining the pasta.
Once the tomatoes are roasted, carefully remove the baking sheet from the oven. You can gently mash some of the tomatoes with the back of a spoon to create a more sauce-like consistency.
Add the drained pasta directly to the baking sheet with the roasted tomatoes and garlic. Toss well to coat the pasta in the tomato juices and oil.
Stir in the chopped fresh basil and grated Parmesan cheese. If the pasta seems a bit dry, add a splash of the reserved pasta water to loosen it up and create a glossy sauce.
Serve immediately, drizzled with a little extra olive oil and topped with additional Parmesan cheese.