Preheat oven to 475 degrees.
Halve tomatoes lengthwise and lay them cut sides down in a jelly-roll pan.
Brush generously with 3 tablespoons oil and sprinkle oregano, basil, and pepper.
Roast tomatoes for 10 minutes. Sprinkle minced garlic over tops and continue roasting for an additional 5 to 12 minutes until tomato edges are charred, looking cooked and releasing their juices. Be careful not to over-roast so garlic won't burn. 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, and wine. Then whisk tomato paste.
Heat the cream and whisk into the tomato mixture.
Taste and add sugar if necessary (the sugar helps cut the acidity of the tomatoes if they happen to be acidic).
Stir in Parmesan. Add salt and pepper to taste and bring soup to a simmer.
NOTE: The type of tomatoes used in this recipe is important. The best are when in season, however store bought vine ripened is also a good selection. The large hard tomatoes found in Supermarkets usually have no taste and will yield an unsatisfactory result. Make sure they are nicely ripened.