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1. Preheat oven to 400 F and line a baking sheet with foil.
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2. Combine tomatoes, balsamic vinegar, red pepper flakes, 2 tablespoons of oil and salt and pepper (to taste) in a large bowl and toss together.
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3. Spread tomato mixture onto the baking sheet.
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4. Cut off the top of the head of garlic (just enough to expose the cloves inside), drizzle 1 tablespoon of oil on top and wrap the head tightly in tin foil. Place garlic on the baking sheet with the tomatoes and roast for about 45 minutes.
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5. Towards the end of the tomatoes and garlic roasting, heat butter and remaining tablespoon of oil in a large heavy bottomed pot over medium heat.
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6. Add onions and the minced garlic and saute until softened, about 5-7 minutes.
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7. Once tomatoes and the head of garlic are done roasting, add them to the pot (you'll have to squeeze the roasted garlic out of the paper first) and continue to cook for another 5 minutes.
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8. Add parsley, broth, tomato paste, brown sugar and cubed bread and simmer for 20-25 minutes uncovered, stirring occasionally.
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9. Add heavy cream and parmesan cheese and stir until combined.
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10. Remove soup from heat and puree with an immersion blender or you can process it in batches with a regular blender until creamy.
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11. Season with salt and pepper to taste.
