Add 2 tablespoons of olive oil, fresh cherry tomatoes and sliced red bell pepper to a large bowl. Season with salt and pepper and toss to combine.
Arrange on a large baking sheet and roast for 20-30 minutes.
Add 2 tablespoons of olive oil to a large pot or Dutch oven over medium heat and cook the onion, celery, salt, pepper, red pepper flakes, paprika, and basil for about 5-6 minutes or until the onions are translucent.
Add in the garlic and stir for 30 seconds before adding in the roasted tomatoes and pepper, broth, crushed tomatoes, and sugar.
Lower the heat to a simmer and cook for 30-40 minutes before blending until perfectly smooth with an immersion blender.
Add in the heavy cream, mix well and serve using more heavy cream and parsley as garnishes.