Crispy Grilled Cheese-Topped Tomato Soup

  • Level: Easy
  • Yield: 4 servings
  • Total: 1 hr 10 min
  • Active: 45 min
A bowl of tomato soup and a grilled cheese is a classic combo, so we decided to take it up a notch by putting the grilled cheese directly on top of the soup: Think French onion soup, but heartier and more colorful. Every bite is equal parts buttery, cheesy sandwich and tangy, savory soup. First, we make a quick homemade tomato soup, then broil up a batch of Cheddar and Muenster sandwiches in the oven. We put them together in classic soup crocks, then broil it all together with (yes!) more cheese on top. You may never think of “soup and sandwich” the same way again.
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Ingredients

Soup:

2 tablespoons olive oil

1 celery stalk, diced

2 cloves garlic, minced

1 shallot, minced

1/4 teaspoon dried oregano

Kosher salt and freshly ground black pepper

2 tablespoons tomato paste

One 28-ounce cans whole, peeled tomatoes

1 bay leaf

2 tablespoons unsalted butter

Grilled Cheese:

2 tablespoons unsalted butter, at room temperature

8 slices of thin white bread, crusts removed

1/4 cup mayonnaise

4 slices Muenster cheese

4 slices sharp Cheddar

4 ounces Colby Jack, shredded

1/4 cup shredded Parmesan

Directions

Special equipment:
four 8-ounce ovensafe soup crocks
  1. For the soup: Heat the olive oil in a large heavy-bottom pot over medium heat. Add the celery, garlic, shallot, oregano, 1 teaspoon salt and a few grinds of black pepper and cook, stirring occasionally, until the vegetables soften, 4 to 5 minutes. Stir in the tomato paste and cook until toasted, 1 to 2 minutes. Add the tomatoes, bay leaf, 3 cups water and 1 1/2 teaspoons salt.
  2. Use a wooden spoon to break up the tomatoes then bring to a simmer over medium heat. Cook, stirring occasionally, until the soup has deepened in flavor and turned a deeper red, 20 to 25 minutes.
  3. Discard the bay leaf. Use an immersion blender to purée the soup (alternatively, working in small batches, ladle the soup into a blender and puree until smooth, then return it to the pot). Stir in the butter until melted. You should have about 4 cups of soup.
  4. Meanwhile, make the grilled cheese: Turn the broiler to high.
  5. Spread the butter on one side of each piece of bread. Then spread the mayonnaise on top of the butter on each piece of bread. Place 4 pieces of bread, mayonnaise-side down, on a baking sheet. Top each piece with 1 slice of Muenster cheese and 1 piece of Cheddar, breaking the cheese up so that it fits inside the bread. Top each with another piece of bread, mayonnaise-side up. Broil until the bottoms of each sandwich have turned golden brown and the cheese is just starting to melt, 2 to 3 minutes.
  6. To assemble, line a baking sheet with foil. Ladle the tomato soup into four 8-ounce ovensafe soup crocks and place them on the prepared baking sheet. Top each crock with a sandwich. Mix the shredded Colby Jack cheese and Parmesan in a medium bowl. Divide the cheese on top of each sandwich. Broil until the cheese has melted and turns golden brown in spots, 2 to 4 minutes depending on your broiler. Carefully serve the soup in the hot crocks.

Let's Get Cooking!

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