Preheat oven to 400F. In baking dish or sheet pan, add the chopped tomatoes, onion, red bell pepper and head of garlic. Drizzle over the olive oil and season with salt, black pepper and Italian seasoning. Roast vegetables in the oven for 40-50 minutes or until softened and slightly charred.
Transfer roasted vegetables (tomatoes, onions and bell pepper) and released juices into a large saucepan. Squeeze in the roasted garlic. Add in the vegetable broth, heavy cream, tomato paste, paprika (optional), brown sugar (optional), salt, black pepper and basil.
Use an immersion blender to purée the ingredients into a smooth soup consistency. (Alternatively, you can use a blender in place of an immersion blender.)
Place saucepan on the stove under medium-low heat and bring the soup to a simmer to warm up.
Spoon desired serving of the soup into a bowl, drizzle over some heavy cream and top with fresh or coarse black pepper (optional). Serve immediately. Enjoy!