Bring a large pot of salted water to a boil. Drop the pasta into the water and cook for 8 to 9 minutes or as directed by the package. Once cooked, drain the pasta and place in a large baking dish or serving platter and drizzle with a little olive oil.
Heat the 2 tablespoons olive oil in a large saute pan over medium-high heat. Add the chopped bacon and cook, stirring occasionally, just until fully crisp. Remove the bacon with a slotted spoon and let drain on a paper towel-lined plate or tray. Leave the bacon grease in the pan.
Heat the pan with the bacon grease over medium-high heat. Add the shrimp, season with salt and black pepper and cook just until pink, 1 to 2 minutes per side. Remove the shrimp from the pan and let rest with the bacon.
Add the garlic, anchovy, olives, oregano and red pepper flakes to the pan and cook, stirring, just until the garlic begins to toast, 3 to 4 minutes. Add the red wine and cook, scraping up any browned bits from the bottom of the pan, until the liquid reduces by half, 1 to 2 minutes.
Add the crushed tomatoes to the pan, reduce the heat to a simmer and cook the sauce for about 5 minutes, stirring occasionally.
Add the cream, bacon and shrimp to the sauce and simmer for 1 minute to bring everything together. Taste the sauce and season with salt and black pepper.
Pour the sauce over the pasta to completely cover it. Or you can toss the pasta into the sauce if your pan is large enough.
To finish the dish, grate the cheese over the top and garnish with the basil and a drizzle of olive oil.