Prep the tomatoes: Open 1 (14-ounce) can good-quality whole peeled tomatoes and fish out enough whole tomatoes to fill about 1 cup or 8 ounces. This should be about 6 - 8 tomatoes.Finely chop the tomatoes. Reserve the remaining liquid/tomatoes for another use, like soup or pasta.
Cook the pasta: Meanwhile, bring a large pot of water to a boil. Season generously with salt and add 8 ounces dried rigatoni. Cook until just before al dente, reserving 1 cup of pasta water for the sauce, then drain the pasta.
Make the sauce: Set a large skillet over medium-low heat, and saute 3 ounces guanciale* until cooked through and crisp, about 8 - 12 minutes. It will quickly transform from translucent to opaque to golden-brown, so keep an eye out! Stir in ¼ teaspoon red chili flakes and ½ small red onion, and saute for 5 - 7 minutes, or until the onion is softened. Add ¼ cup dry white wine (if using), bring to a boil, and simmer for 2 - 4 minutes until the wine has reduced. Use a wooden spoon to pick up any bits from the bottom of the pan.Add the chopped tomatoes, and simmer for 10 - 15 minutes, crushing any larger bits of tomato with the back of a wooden spoon to help form a sauce. Once the sauce no longer has a raw, bracing acidic taste, it's ready. Taste and season with salt as desired.
Finish: Still over medium-low heat, add the pasta into the pan, and half the cheese, and toss to coat, adding a little pasta water as needed to loosen the sauce. Allow the mixture to thicken slightly until the pasta clings nicely to the sauce, then divide amongst serving bowls and top with the remaining cheese. Serve immediately and enjoy!
Notes
Recipe adapted from Chef Evan Funke's recipe at Felix Trattoria.* Guanciale is a cured (unsmoked) pork made from the jowl or cheek of the pig. It can be difficult to find in the US, but I've had success at specialty cheese stores, butcher shops, Eataly and Amazon. Because of its high fat content, I recommend slicing it chilled.TIP: If you're struggling, I recommend seeking a good quality pancetta or thick-cut bacon, at least ¼-inch thick. Pancetta is also not smoked, so it will be more similar to guanciale but slightly less fatty. Since bacon is smoked, it will yield a relatively different, albeit tasty, flavor.White wine (optional): Even though we're just using a splash, it's essential to look for a dry white wine for the best flavor. For a super traditional pairing, look for Trebbiano d’Abruzzo. Pinot Grigio is another excellent option. You can also omit this if you don't have it!