Butter, for greasing
1 (28-ounce) can crushed tomatoes
1 clove garlic, coarsely chopped
1/2 pound (8 ounces) mezze penne or other small pasta
1/3 cup olive oil, plus extra for drizzling
1/4 cup dried oregano
2 tsp kosher salt
1/2 tsp freshly ground black pepper
4 to 5 very ripe, extra-large or beefsteak tomatoes, cut into 1/2-inch thick slices
Put an oven rack in the center of the oven. Preheat the oven to 450°. Butter an 8 by 8-inch baking dish. Set aside.
In a food processor, blend together the crushed tomatoes and garlic. Pour into a medium bowl and add the uncooked pasta, 1/3 cup olive oil, oregano, salt and pepper. (Be sure to use a small pasta, i just used a regular penne and some of the pasta didn't cook all the way!) Toss until all the ingredients are coated.
Line the bottom and sides of the baking dish with tomato slices. Pour the pasta mixture into the pan and spread evenly. Arrange the remaining tomato slices in an overlapping layer on top of the pasta mixture, making sure the mixture is completely covered. Drizzle with olive oil. Bake until the tomatoes are slightly crispy and the pasta is cooked, about 1 hour. Remove from the oven and cool for 5 minutes before serving.