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The classic combo of tomato soup and grilled cheese gets a flavorful update thanks to Rach's addition of pimento cheese and fire-roasted tomatoes.
For the sandwiches, in a food processor, combine cheese, cream cheese, pimientos, garlic, mustard, hot sauce, Worcestershire, and paprika. Lightly butter one side of sliced bread and build pimiento cheese sandwiches, buttered sides facing out. Preheat a large griddle or cast iron skillet over medium heat when you are ready to grill them. (You can omit butter and griddle the sandwiches in a hot panini press as well.)
For the soup, heat a soup pot over medium-high heat with EVOO, 2 turns of the pan, add the onion and season with salt and pepper, cook to soften 3 minutes, then add red peppers, garlic, pimenton, tomato paste, and stock. Soften 4-5 minutes partially covered, then add tomatoes and heat through. Puree with stick blender. Reduce heat to low and simmer, then stir in cream, if using, to serve.