I love the jumble of potent flavors typically found in puttanesca sauce: capers, black olives, anchovy, garlic, tomatoes. But often, there's just too much of it. I like to pull back a bit on the amounts, so that the flavors of the dish, instead of coming on in full force with diminishing returns, continue to build, until by the time you're done, you're wishing there was more. I like to use a mix of plum tomatoes and cherry tomatoes, but you can just as easily omit one and double the amount of the other.
In a small skillet, warm the olive oil over medium heat. Add the anchovies and cook, breaking them up with a fork or wooden spoon, until they have disintegrated into the olive oil. Add the shallot, garlic, and crushed red pepper and cook, stirring, until they just begin to brown. Then add the oregano, if using.
To peel the plum tomatoes, use a paring knife to cut a small x on the tomato. Bring a saucepan of water to a boil, and have ready a bowl of ice water. Boil the tomatoes for about 10 seconds, then plunge them into the ice bath. The shock of going from hot to cold should cause the skin to contract, making it easier to peel. Use your fingers or a small paring knife to pull the skin off. If the skin is stubborn, try boiling and shocking the tomato again.
Cut the plum tomatoes into 8 pieces and the cherry tomatoes in halves or quarters depending on size. In a bowl, combine the cherry tomatoes, plum tomatoes and parsley. Add the capers and olives and let this mixture sit for a few minutes or up to an hour at room temperature for the combined flavors to develop. (Refrigerate it for any longer stretches and use it within 24 hours.)
When ready to serve, bring a large pot of salted water to a boil and cook the spaghetti until just shy of al dente. Before draining, reserve about 1/2 cup of the cooking water. When the pasta is just about done, heat a large skillet over medium-high heat. Add a couple of tablespoons of the olive oil, and when hot, add the tomato mixture to the pan. (You want the tomatoes to have enough surface space so that when they hit the pan, the liquid that is released from them evaporates almost immediately.)
Drain the spaghetti, add it to the skillet, and use tongs to toss it with all of the ingredients. Add some of the pasta cooking liquid to the pan as necessary to keep the pasta moist. Transfer the spaghetti to warm bowls and drizzle with a little more of the remaining olive oil and some fresh chopped parsley, if you like.
Which wine? A Greco di Tufo (DOC) from Campania would really allow this dish to shine. A rich white wine made from Greco grapes, this wine offers a smokiness that's nicely tamed by the assertive flavors of the puttanesca.