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Preheat oven to 400°F (200°C). Spread tomatoes on a baking sheet, drizzle with 2 tbsp olive oil, sprinkle with ½ tsp salt and pepper. Roast for 50–60 minutes.
In a large pot, heat remaining olive oil over medium heat. Sauté onion 5–6 minutes. Add garlic and cook 1 minute more.
Add roasted tomatoes (with juices), broth, basil, Italian seasoning, sugar, and remaining salt. Simmer 10–15 minutes.
Use an immersion blender or blend in batches until smooth.
Stir in heavy cream. Warm through for 5 more minutes on low heat.
Serve hot with optional garnish of fresh basil and Parmesan.