Grilled Cheese With Creamy Tomato Soup

In 'Williams-Sonoma: Comfort Food'

• Ready In: 1 hr 59 mins
• Serves: 4

Ingredients

• Creamy Tomato Soup

• 4  lbs plum tomatoes
• 2  tablespoons olive oil
• 1  tablespoon unsalted butter
• 2  stalks celery, finely chopped
• 1⁄3 cup  finely chopped shallot
• 1⁄2 cup  chicken stock (or as needed)
• 1  teaspoon  chopped fresh thyme
• 1⁄2 teaspoon sugar
• 1⁄2 cup heavy cream
•  kosher salt
•  fresh ground pepper

• Grilled Cheese

• 3⁄4 lb cheddar cheese, thinly sliced
• 8  slices  sourdough bread (or pain au levain)
• 4  tablespoons unsalted butter, at room temperature

Directions

1. Soup-preheat oven to 400°.
2. Lightly oil a rimmed baking sheet.
3. Cut the tomatoes in half lengthwise.
4. Place them, cut side up, on the prepared baking sheet and brush with 2 tablespoons oil.
5. Roast until the tomatoes look somewhat shriveled, about 45 minutes.
6. Let cool for about 20 minutes.
7. Transfer the tomatoes and any juices to a food processor.
8. Pulse until chopped, then rub the tomatoes and their juices through a coarse-mesh sieve placed over a bowl.
9. You should have about 3 1/2 Celsius tomato puree.
10. Discard the contents of the sieve.
11. In a large saucepan, melt the butter over med-low heat.
12. Add the celery and cook, stirring occasionally, until tender, about 5 minutes.
13. Add the shallots and cook, stirring occasionally, until softened, about 3 minutes.
14. Stir in the tomato puree, 1/2 cup stock, and thyme; bring to a simmer over med-high heat.
15. Decrease heat to med-low and simmer, uncovered for about 15 minutes.
16. Stir in the sugar.
17. In 3 or 4 batches, transfer the soup to a blender and process until smooth.
18. Transfer to a clean saucepan, add the cream and heat until piping hot but not boiling.
19. If the soup seems thick, thin with more stock.
20. Season to taste with salt and pepper.
21. Sandwiches-heat a griddle or 2 large frying pans over medium heat until hot.
22. For each sandwich, place 1/4 of the cheese on top of 1 bread slice and top with a second bread slice.
23. Spread the outsides of each sandwich with 1 tablespoon of the butter.
24. Place on the griddle, decrease heat to med-low, and cook until the undersides are golden brown, 3-4 minutes.
25. Flip the sandwiches and brown the other side, 3-4 minutes.
26. Ladle the soup into warmed bowls.
27. Serve at once, with the hot sandwiches alongside.