Preheat your oven to 400°F and arrange halved Roma tomatoes cut-side up on a baking sheet. Drizzle with 2 tbsp olive oil, season with salt and pepper, then roast for 25 minutes until the edges caramelize and tomatoes collapse slightly.
While tomatoes roast, heat the remaining 2 tbsp olive oil in a large pot over medium heat. Sauté your diced onion for 5 minutes until softened and translucent, stirring occasionally so it doesn't brown.
Add minced garlic and red pepper flakes to the pot, stirring constantly for 30 seconds until fragrant. This brief cooking time prevents the garlic from burning while building flavor depth.
Remove the roasted tomatoes from the oven and add them to the pot along with the vegetable broth. Simmer for 10 minutes to let flavors meld, then carefully blend using an immersion blender until smooth, or transfer to a regular blender in batches.
Stir in the heavy cream, butter, fresh lemon juice, and balsamic vinegar, heating through without boiling for 2-3 minutes. The creamy savory roasted tomato basil soup recipe is almost ready—just needs fresh basil.
Turn off the heat and stir in fresh basil leaves and grated Parmesan cheese, reserving some basil for garnish. Taste and adjust seasonings, adding more salt or lemon juice as needed for balance.
Ladle into bowls and garnish with fresh basil, cracked black pepper, and a drizzle of quality olive oil. Serve immediately while steaming hot.