Heat 1/4 cup extra virgin olive oil in a large pan over low heat. Add the crushed garlic and cook gently for 2–3 minutes until fragrant and softened but not browned.
Add the whole peeled tomatoes with their juice and 8 basil leaves to the pan. Break the tomatoes up with the back of a spoon or spatula.
Simmer the tomatoes on low for about 20 minutes, stirring occasionally and continuing to break them down until the sauce is reduced.
Puree the sauce until smooth with a blender or immersion blender, then return the sauce to the pan and cook over low heat for 10 more minutes. Season with salt, pepper, and sugar as needed.
Meanwhile, bring a large pot of water to a boil. Add 1 tablespoon salt, then add 10 oz rigatoni and cook until 1 minute less than the package instructions.
Reserve 1 cup of the pasta cooking water, then drain the rigatoni.
Add the drained pasta to the sauce and toss with tongs over low heat until fully coated. Add some reserved pasta water a little at a time if the sauce needs loosening and cook for about 1 minute to marry the pasta and sauce.
Adjust seasoning, then serve topped with extra basil leaves, grated Parmesan, and a drizzle of extra virgin olive oil.