Bring a large pot of lightly salted water to a boil. Add penne and cook, stirring occasionally, until tender yet firm to the bite, about 11 minutes.
Place bacon in a large saucepan and cook over medium heat, turning occasionally, until crisp, about 5 minutes. Drain bacon on paper towels.
Return saucepan to medium-low heat. Add onion and garlic; cook and stir until onion is translucent, about 3 minutes. Increase heat to high; add vodka and bring to a boil. Cook until reduced by 1/2, about 2 minutes. Stir in tomatoes, heavy cream, Worcestershire sauce, and red pepper flakes. Reduce heat to a simmer and cook sauce until thickened, about 10 minutes.
Drain pasta; top with the sauce and sprinkle with the bacon, basil, and black pepper.