Preheat oven to 375 degrees and prepare a baking sheet with foil or use a nonstick baking sheet. Thoroughly rinse produce and pat dry. Thinly slice basil. Coarsely chop garlic. Slice shallot into thin strips. Cut radicchio heat into 1/2" pieces.

Place the bacon strips on the baking sheet. Bake in the oven for 8-10 minutes, or until bacon is crispy and browned. Remove bacon from baking sheet and place bacon on a paper towel-lined plate. Reserve 1 Tbsp. of bacon drippings from the pan for the pasta. Once bacon has cooled, chop into 1/4" pieces and reserve.

Bring a large pot of lightly salted water to a rolling boil. Put a colander in the sink. Add penne pasta to the boiling water and stir gently for a minute to break up the pasta. Return to a boil. (For authentic "al dente" pasta, boil uncovered, stirring occasionally for 10 minutes. For more tender pasta, boil for 1 additional minute.) Remove from heat, drain, and cool with cold running water to stop the cooking process.

Heat 1 Tbsp. olive oil, 1 Tbsp. bacon drippings, onion, and garlic in a medium pot over medium heat, about 3 minutes. Add chopped bacon, pasta, radicchio, and baby arugula and cook for 4-5 minutes, or until radicchio and arugula are wilted. Add salt, pepper, and red pepper flakes to taste.

In a shallow bowl or dish, compose a mound of pasta. Garnish with basil, Parmesan cheese, and a crack of fresh black pepper. If pasta is a little dry, drizzle with 1 tsp. olive oil before serving.