Halve tomatoes lengthwise and lay them cut sides down in a jelly-roll pan. Brush generously with 3 tablespoons oil and sprinkle with garlic, oregano, basil, and pepper. Roast tomatoes until their edges are charred, about 15 to 20 minutes.
Scrape tomatoes, oil, and herbs from pan into food processor. Process until not quite smooth (leaving small chunks and charred black specks).
In a saucepan cook onion in remaining 2 tablespoons oil until translucent. Whisk in roasted tomato puree, broth, salt, and wine. Then whisk tomato paste. Heat the cream and whisk in to the tomato mixture. Taste and add salt and pepper if necessary. Stir in Parmesan and bring soup to a simmer.