On a baking sheet, place the halved cherry tomatoes. Drizzle with 2 tablespoons of olive oil and season with salt, pepper, minced garlic, oregano, and basil. Toss to combine.
Roast the tomatoes in the preheated oven for about 25-30 minutes, or until they are soft and slightly caramelized.
While the tomatoes are roasting, cook the pasta according to the package instructions until al dente. Drain and set aside, reserving 1 cup of pasta water.
In a large skillet over medium heat, add the remaining tablespoon of olive oil. Once hot, pour in the roasted tomatoes with all the juices.
Stir in the heavy cream and bring to a simmer, allowing it to thicken slightly for about 3-5 minutes.
Gradually add the grated Parmesan cheese, stirring until melted and smooth. If the sauce is too thick, add reserved pasta water a little at a time until you reach your desired consistency.
Add the cooked pasta to the sauce, tossing to coat evenly. If desired, sprinkle in crushed red pepper flakes for extra heat.
Serve immediately, garnished with fresh basil leaves and additional Parmesan cheese on top.
Notes
Add crushed red pepper flakes for extra heat if desired.