Classic Grilled Cheese + Cream of Tomato Soup

Heat oven to 450°F. Line a rimmed baking sheet with foil. Place a strainer over a large bowl, and open the first can of tomatoes into it. With fingers, carefully open whole tomatoes and push out seeds, allowing juices to fall through the strainer into the bowl. Spread seeded tomatoes in a single layer on foil. Repeat with the second can of tomatoes. Sprinkle tomatoes on roasting pan evenly with brown sugar. Bake until all liquid has evaporated, and tomatoes begin to color, about 30 minutes. Let tomatoes cool slightly while you work on the rest of the soup.

Heat butter over medium heat in a large saucepan until foaming. Add shallots, tomato paste, and allspice. Reduce heat to low, cover, and cook, stirring occasionally, until shallots are softened, 7 to 10 minutes. Add flour and cook, stirring constantly, until thoroughly combined, about 30 seconds. Gradually add vegetable or chicken stock, whisking constantly to combine; stir in the reserved tomato juice. Gently peel roasted tomatoes from foil and add them to the pot. Cover, increase heat to medium, and bring to a boil. Reduce heat to low and simmer, stirring occasionally, to blend flavors, about 10 minutes.

Off the heat, use an immersion blender to puree soup until smooth. Add cream — start with just 1/4 cup, adding the last 1/4 cup, if desired, drizzled over serving bowls — warm over low heat until hot, about 3 minutes. Off heat, stir in brandy and season with salt and cayenne. Serve immediately.

For grilled cheese: Heat a heavy 12-inch skillet over low to medium-low heat. Meanwhile, sprinkle a portion of cheese over two bread slices. Top each with a remaining bread slice, pressing down gently to set. Brush sandwich tops completely with half of melted butter; place each sandwich, buttered-side down, in skillet. Brush the remaining side of each sandwich completely with remaining butter. Cook until crisp and deep golden brown, 5 to 10 minutes per side, flipping sandwiches back to the first side to reheat and crisp, about 15 seconds. Serve immediately.