Heat 1/4 cup extra virgin olive oil in a large sauté pan over low heat. Add the crushed garlic and cook gently for 2–3 minutes until fragrant and soft, taking care not to brown it.
Add the whole peeled tomatoes (including their juice) and 8 basil leaves to the pan. Break the tomatoes up with the back of a spoon or spatula.
Simmer the tomatoes over low heat for about 20 minutes, stirring occasionally and breaking down the tomatoes until saucy.
Carefully puree the sauce until smooth using a blender or immersion blender, then return the sauce to the pan and simmer over low heat for an additional 10 minutes. Season with salt, pepper, and sugar to taste.
Bring a large pot of salted water to a boil (use about 1 tablespoon salt). Add the rigatoni and cook for 1 minute less than the package instructions, reserving 1 cup of the pasta cooking water before draining.
Add the drained rigatoni to the sauce and toss with tongs over low heat until the pasta is fully coated, adding reserved pasta water a little at a time if the sauce seems dry. Cook for about 1 minute to let the flavors marry.
Taste and adjust seasoning. Serve topped with extra basil leaves, grated Parmesan, and a drizzle of extra virgin olive oil.