4 lb tomatoes, halved lengthwise
6 garlic cloves, left unpeeled (just roast one whole garlic bulb)
3 tablespoons olive oil
1/2 teaspoon salt
1/4 teaspoon black pepper
1 medium onion, finely chopped
1/2 teaspoon dried oregano, crumbled
2 tablespoons unsalted butter
2 teaspoons sugar (I omit this altogether!!)
3 cups chicken stock or low-sodium broth
1/2 cup heavy cream (optional, I don’t use it)
6 medium to large size fresh basil leaves
Put oven rack in middle position and preheat to 350°F.
Arrange tomatoes, cut sides up, in 1 layer in a large shallow baking pan and add garlic to pan. Drizzle tomatoes with oil and sprinkle with salt and pepper. Roast tomatoes and garlic 1 hour, then cool in pan on a rack. Peel garlic. (** I do the garlic bulb separate, wrapped in foil w/olive oil, salt & pepper at 400 degrees for about 30 minutes)
Cook onion and oregano in butter in a 6- to 8-quart heavy pot over moderately low heat, stirring frequently, until onion is softened, about 5 minutes. Add tomatoes, garlic, and stock and simmer, covered, 20 minutes.
Purée soup in batches in a blender (use caution when blending hot liquids), then force through a sieve into cleaned pot, discarding solids. Stir in cream and salt and pepper to taste and simmer 2 minutes.