The Perfect Grilled Cheese & Tomato Soup


Grilled Cheese:
1 Challah or brioche, sliced into approximately ½ inch thick slices
3 slices per sandwich fontina
3 slices per sandwich cheddar
½ cup Parmesan, grated on large whole grater
¼ teaspoon butter

Layer the bread with slices of fontina and cheddar cheese.  Heat the butter in a nonstick pan over medium heat and allow it to foam.  Sprinkle half the parmesan into the pan and place the sandwich on top.  Cook until golden brown and the cheese forms a crispy crust.  Repeat with the other side, never allow it to get to dark brown.  Lower the heat if the cheese in the center hasn’t melted and cover if necessary to make sure its melts well.
Serve with tomato soup.

Tomato Soup:
4 cups canned San Marzano chopped tomatoes (drained, juice reserved)
4 tablespoons unsalted butter
2 cloves garlic, chopped
1 cup shallots, minced
2 tablespoons tomato paste
3½ cups tomato juice reserved from can
2 cups chicken stock
¼ cup heavy cream
2 tablespoons dry sherry
Salt and pepper to taste

Adjust oven rack to upper-middle position and heat oven to 450˚F; line sheet pan with parchment paper.  Spread tomatoes in single layer on parchment paper.  Bake until all liquid has evaporated and tomatoes begin to color, about 15 minutes.  Let tomatoes cool slightly, then remove from parchment paper.

Heat butter over medium heat in saucepan until foaming; add garlic, shallots and tomato paste.  Reduce heat to low, cover, and cook, stirring occasionally, until shallots are softened, 7 to 10 minutes.  Whisking constantly, gradually add chicken stock; stir in reserved tomato juice and roasted tomatoes.  Cover, increase heat to medium, and bring to boil.  Reduce heat to low and simmer, stirring occasionally, to blend flavors, about 15 minutes.  Puree mixture until smooth.  Return the pureed mixture to a saucepan, add cream, and heat over low heat until hot, about 3 minutes.  Shut off heat, stir in sherry; season to taste with salt and pepper.