Heat oil and butter in a large pot over medium heat until butter is melted and pan is hot.
Add onion and cook, stirring, until softened (about 3-5 minutes).
Add garlic and cook until fragrant (about 30 seconds).
Add vodka and cook, scraping the bottom of the pot, until vodka is reduced by about half and you no longer get slapped in the face by the smell of alcohol if you whiff the steam.
Add tomato paste, Italian seasoning, salt, pepper, and red pepper flakes and cook, stirring, until mixture is smooth and tomato paste is well incorporated.
Add whole tomatoes, breaking them up with your spatula or spoon.
Drizzle in cream and stir until well-combined. Use your immersion blender to puree the sauce until smooth (if you don’t have an immersion blender, transfer sauce to a blender and puree there, then return to the pot).
Reduce heat and simmer for at least 30 minutes, stirring occasionally. Prepare pasta while mixture simmers.
Cook penne pasta in well-salted water according to package instructions. When finished cooking, reserve 1 cup of pasta water before draining.
Add cooked, drained pasta to pot with a splash of reserved pasta water and add grated parmesan and sliced basil. Stir well and continue to simmer over low heat. If mixture becomes too thick, add additional reserved pasta water as needed (you won’t need the full cup, but I like to have spare water for leftovers the next day).
Serve, topped with additional grated parmesan and fresh basil if desired.