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Heat olive oil in a large stock pot or Dutch oven over medium. Add onion and cook until soft, about 8 minutes. Stir in garlic and cook 1 more minute.Add crushed tomatoes, roasted red peppers (and residual juices in jar), and broth; bring mixture to a simmer.Gently simmer over medium heat for about 15 minutes, until the mixture slightly reduces. Season with salt and black pepper, and reduce heat to low.
Use am immersion blender or countertop blender to blend soup until smooth. Stir in heavy cream and Parmesan; taste and adjust seasonings as needed.Ladle into bowls and top with extra cracked black pepper and garnishes of choice (fresh basil leaves, extra Parmesan, a swirl of heavy cream or drizzle of olive oil.)