In cold large skillet, add guanciale to pan and set to medium heat
Cook guanciale, rendering fat, until crispy.
Remove guanciale with a slotted spoon and set on a paper towel lined plate, reserving fat in pan
Turn pan up to medium high heat and add onion and crushed red pepper. Cook until onions are translucent – about 8 minutes
Add in garlic and cook until fragrant – no longer than 1 minute; Add wine here if using and reduce
Stir in tomatoes. Add in sugar and bring to a boil. Reduce to a simmer and cook for 30 to 40 minutes until sauce is reduced and cooked through
While sauce is reducing, bring large pot of salted water to boil
Cook pasta until al dente just before sauce has finished cooking.
Add guanciale (reserving some for plating) and pasta to sauce and toss together. Add basil if using at this time
Remove pan from heat and stir in pecorino until incorporated into sauce
Plate pasta topping with additional guanciale, pecorino, and basil if using