In a small skillet, warm the olive oil over medium heat. Add the anchovies and cook, breaking them up with a 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. Add the capers and olives and remove the pan from the heat.
In a bowl, combine the cherry tomatoes, plum tomatoes, parsley, and oregano, if using. Use a flexible spatula to scrape out all of the caper and olive mixture and add it to the bowl with the tomatoes. Let this mixture sit for a few minutes or up to an hour at room temperature for the combined flavors to develop.
When ready to serve, bring a large pot of salted water to a boil and cook the pasta until just shy of al dente. Before draining, reserve about ½ cup of the cooking water.
When the pasta is just about done, heat a large skillet over medium-high heat. Add a couple 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 pasta and 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 pasta to warm bowls and drizzle with a little more of the remaining olive oil and some fresh chopped parsley, if you like.