Grilled Cheese & Roasted Tomato Soup

A quintessential comfort food pairing that will put a smile on anyones face.

Prep Time15

Cook Time45

Total Time1

Course: Main Course

Cuisine: American

Servings: 4

8 large roma tomatoes, halved (about 2 pounds)
2 medium yellow onions, peeled and halved
a medium bulb of garlic, top removed
1/4 cup of olive oil
salt and black pepper
2 tablespoons of brown sugar
several sprigs of fresh thyme and oregano (or a teaspoon of dried italian herbs)
2 tablespoons of butter
2-3 cups of stock (chicken or vegetable)
1/4 cup of heavy cream
fresh basil leaves (optional)
a pinch of crushed red pepper flakes
1/2 cup of parmesan, grated or shredded

Preheat your oven to 400 degrees
Place the halved tomatoes, onions and garlic bulb (cut side up) on a large baking sheet
Drizzle 1/4 cup of olive oil over everything, toss to coat and season generously with salt and black pepper
Sprinkle 2 tablespoons of brown sugar over the onions and add the fresh thyme and oregano
Roast the tomatoes, onions and garlic for 45 minutes

Place a large skillet over medium heat
Spread a tablespoon of mayonnaise over one side of each slice of bread
Place one slice, mayonnaise side down onto the skillet and top with 2 slices of cheese and 2 ounces of shredded cheese
Add the other slice of bread, mayonnaise side up
Cook until the underside of the sandwich is crisp and golden brown and then carefully flip the sandwich and cook until the other side is golden brown and the cheese is fully melted

Remove the thyme and oregano and transfer the roasted tomatoes and caramelized onions into a blender
Squeeze the roasted garlic cloves out of the bulb and place them in the blender
Add 2 tablespoons of butter, 1/4 cup of heavy cream, 2 cups of vegetable stock, some fresh basil leaves, a pinch of red pepper flakes, a pinch of salt and 1/2 cup of finely shredded parmesan into the blender
Blend until smooth, adding additional stock to thin if necessary