Preheat your oven to 450°F. Cut the Campari or vine tomatoes in half and place them into a large casserole dish or deep baking dish. Add the onion wedges and garlic cloves, making sure to halve or quarter any particularly large cloves for even cooking. Drizzle everything evenly with olive oil and season with kosher salt, dried oregano, and smoked paprika. Toss to coat all the vegetables, then spread them out as evenly as possible. Roast in the oven for 30-40 minutes, stirring the vegetables around halfway through to ensure even caramelization.

Once the vegetables are roasted and slightly cooled, transfer them along with all of their juices into a large pot. Add the fresh basil. Using an immersion blender, puree everything until perfectly smooth. Alternatively, you can transfer the mixture in batches to a blender and blend until creamy, then return the soup to the pot. This step builds the base flavor for your soup.

Pour in the vegetable broth (or chicken stock) and heavy cream into the blended vegetable mixture. Stir thoroughly to combine into a silky, creamy soup. Warm gently on the stove if necessary and taste for seasoning. If the soup is too acidic for your preference, I suggest adding a small spoonful of sugar at this point to balance the flavors. Adjust salt or other seasonings to your liking.

Ladle the hot soup into bowls. For a touch of extra richness, swirl a spoonful of heavy cream into each bowl and sprinkle with chopped fresh basil to garnish. Serve with your favorite side, like grilled cheese or a crisp salad, and enjoy! For a more vibrant, fresh flavor, I like to use extra basil right before serving.