In a large skillet, heat olive oil over medium heat. Add guanciale or pancetta and red pepper flakes. Cook, stirring, until lightly browned, about 4-5 minutes. Carefully, add wine and cook, scraping up any browned bits on bottom of pan, until nearly evaporated, about 3 minutes.
Add tomatoes, reduce heat to low, simmer stirring occasionally until sauce thickens; season with salt and pepper.
Meanwhile, In a large pot, boil pasta in salted water until al dente, about 1 minute less than package recommends. Using tongs, transfer pasta to sauce, along with 1/4 cup pasta cooking water. Cook over medium-high heat, stirring and tossing rapidly, until pasta is al dente and sauce has thickened and begins to coat noodles. Remove from heat, add cheese; stir to combine.
Divide among bowls, serve immediately, passing more cheese and red pepper flakes at the table.
Cook’s Note: If you can’t find guanciale you can substitute pancetta.