Preheat your oven to 400°F (200°C).
In a large bowl, combine the halved cherry tomatoes, olive oil, sliced garlic, dried oregano, and red pepper flakes (if using). Season generously with salt and freshly ground black pepper. Toss gently to coat everything evenly.
Spread the tomato mixture in a single layer on a large baking sheet. Ensure the tomatoes are not overcrowded for optimal roasting.
Roast for 20-25 minutes, or until the tomatoes have softened, blistered, and begun to release their juices. The garlic should be fragrant and lightly golden.
While the tomatoes are roasting, cook the pasta according to package directions in a large pot of salted boiling water. Reserve about 1/2 cup of the pasta water before draining.
Once the tomatoes are roasted, carefully transfer them and their juices from the baking sheet into the pot with the drained pasta. Add the torn basil leaves and Parmesan cheese (if using).
Toss everything together, adding a splash of the reserved pasta water as needed to create a light sauce that coats the pasta beautifully. Adjust seasoning if necessary.
Serve immediately, garnished with extra basil and Parmesan if desired.