Arrange a cooling rack over a parchment or foil-lined baking sheet for easy clean up.
Cut the ends off the entire head garlic to expose all of the cloves. Season the garlic with a little salt, some black pepper, and a drizzle of extra-virgin olive oil, then wrap in foil.
Cut the tomatoes in 1/2 and place in a bowl. Lightly dress the tomatoes by drizzling with extra-virgin olive oil. Season the tomatoes with salt, pepper, and marjoram, and arrange on the baking sheet cut-side down. Bake the tomatoes 20 to 25 minutes, then flip the tomatoes, and roast 20 minutes more. Roast the garlic 45 to 50 minutes alongside the tomatoes.
Place about 2/3 of the tomatoes in a food processor. Coarsely chop the remainder of the tomatoes, and reserve. Squeeze the garlic out of its skin, and add to the food processor pulsing until smooth. Add the mixture to a Dutch oven and add the olives, anchovies, capers, and chile. Cook for 5 minutes to allow the flavors to meld. Transfer to a small container for a make-ahead meal and refrigerate, or transfer to a serving bowl. Store the chopped tomatoes separately, or add to the serving bowl.
To serve, bring water to a boil, salt the water and cook the pasta to al dente. Reheat the sauce. Toss the pasta with the sauce for 1 minute, to coat. Serve in shallow bowls with lots of parsley, and drizzle with more extra-virgin olive oil.