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Preheat your oven to 375 degrees F.
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Heat olive oil in a large ovenproof pan. I used my Le Creuset Dutch oven. Add the chopped onions and garlic and saute for about 5 minutes. You want the onions to be translucent but you need to watch the garlic carefully; You don't want to burn it. Add the red pepper flakes and dried oregano and continue cooking for one more minute. Stir in the vodka and simmer the mixture for 5 to 7 minutes. You want the sauce mixture to reduce by half. Set aside.
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Drain the canned tomatoes and crush them with your hands. Add the tomatoes to the pan with the onion mixture. Add 2 t. salt and 1/2 t. black pepper. Stir. Cover the pan with a tight-fitting lid and place the sauce mixture in the preheated oven. Bake for 1 1/2 hours. Once the sauce has baked in the oven, remove the pan from the oven and cool for 15 minutes.
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While the sauce is baking, prepare your penne pasta. Heat a large pot of water until it is boiling, add the pasta and cook until the pasta is al dente. Drain the cooked pasta. Return the pasta to the pot. Toss with a little olive oil (or butter) to keep the penne from sticking together. Set aside.
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Blend the tomato sauce mixture in a food processor or blender (in batches) until the sauce is smooth. Return the sauce to the pan and reheat the sauce and add 1 T. fresh oregano and heavy cream. Stir. (Add more cream if necessary to yield a smooth sauce). Add salt and pepper to taste. Simmer the sauce for 10 minutes.
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Stir about 1/2 C. of the Parmesan into the sauce and stir until the cheese melts into the sauce.
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You can either mix the cooked pasta into the sauce at this point or serve the pasta separately with dollops of sauce on top (as I did here). Just before serving, top the dish with a sprinkle of fresh oregano and grated cheese. Garnish with basil leaves.