grilled cheese and tomato soup
I will admit that I cheat here on weeknights and open up a can of Annie's Tomato Bisque... which is scrumptious. So don't feel like you have to make this whole thing from scratch - just the grilled cheese part.
3 ounces cheese (preferably cheddar, but a combination of cheese will work too), coarsely grated (about 3/4 cup)
4 slices (1/2 inch-thick) from white sandwich bread (ATK likes Pepperidge Farm Toasting White)
2 tablespoons butter (preferably salted), melted
2 (28-ounce) cans whole tomatoes packed in juice
1 1/2 tablespoons dark brown sugar
4 tablespoons unsalted butter
4 large shallots, minced (about 1/2 cup)
1 tablespoon tomato paste
Pinch ground allspice
2 tablespoon all-purpose flour
1 3/4 cups vegetable or chicken stock
1/2 cup heavy cream
2 tablespoons brandy or dry sherry (optional)
Salt and cayenne pepper
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-size down, in skillet. Brush 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 first side to reheat and crisp, about 15 seconds. Serve immediately.
Heat oven to 450°F. Lined rimmed baking sheet with foil. Place a strainer over a large bowl, and open first can of tomatoes into it. With fingers, carefully open whole tomatoes and push out seeds, allowing juices to fall through strainer into bowl. Spread seeded tomatoes in single layer on foil. Repeat with second can of tomatoes. Sprinkle tomatoes on roasting pan evenly with brown sugar. Bake until all liquid has evaporated and tomatoes begin to color (although I usually get just a hint of color, at most), about 30 minutes. Let tomatoes cool slightly while you work on the rest of the soup.
Heat butter over medium heat in 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 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 — I often start with just 1/4 cup, adding the last 1/4 cup, if we wish, 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.
Do ahead: Soup can be refrigerated in an airtight container for up to 2 days. Warm over low heat until hot; do not boil.