1cupshredded cheddar cheeseor Swiss, colby jack, mozzarella, etc.
For the tomato soup:
In a medium pot set to medium heat, add olive oil. Once hot, add shallot, garlic, red pepper flakes, basil, salt and pepper. Cook, stirring frequently until shallots are soft, about 3-5 minutes.
Stir in broth, tomatoes and brown sugar. Cover pot and bring to a boil. Reduce heat and simmer until tomatoes are soft and able to be gently mashed with a fork, about 30 minutes.
Puree with an immersion blender, or add mixture to a food processor or blender, and puree in batches if necessary. Return to pot, off heat, and cover until ready to serve.
For the croutons:
Set a grill pan to medium-high heat. Spread 1/2 tablespoon butter on 1 side of each bread slice. Turn the slices over. Top 2 slices with cheddar. Place remaining 2 slices of bread on top, buttered sides up. Add sandwich to pan and grill until the bread is golden and the cheese is melted, about 2-3 minutes per side. Let cool for 1 minute and cut into 1-inch cubes.
Ladle soup into serving bowls and top with grilled cheese croutons. Sprinkle with chopped parsley or basil, if desired.
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