1 tablespoon extra-virgin olive oil
1 sweet onion, diced
2 garlic cloves, minced
One 28-ounce can plum tomatoes
2 cups vegetable or chicken broth
⅓ cup half-and-half or heavy cream
1 bay leaf
Kosher salt and freshly ground black pepper
Parsley, as needed to garnish
Bread Bowls:
4 small round bread loaves (preferably sourdough)
6 tablespoons room temperature unsalted butter, divided
16 slices American cheese
Make the Tomato Soup: In a medium pot, heat the olive oil over medium heat. Add the onion and sauté until translucent, about 5 minutes. Add the garlic and sauté until fragrant, 1 minute more. Stir in the tomatoes and use a wooden spoon to lightly crush them. Stir in the broth and half-and-half. Add the bay leaf; season with salt and pepper. Bring the soup to a simmer and cook until good flavor develops, 20 to 25 minutes. Make the Bread Bowls: Preheat the oven to 400°F. Line a baking sheet with parchment paper. Slice the tops off the loaves of bread. Use a small knife to cut around the inside of each loaf in a neat circle; remove the circle in one piece and reserve. Rub the inside of each bread bowl with ½ tablespoon butter; line each with 3 slices of American cheese. Transfer to the baking sheet. Meanwhile, slice the reserved bread circles in half horizontally. Butter one side of each piece with ½ tablespoon butter. Place 1 slice of American cheese (torn up if needed to make it fit inside) in between the two slices (buttered sides facing outward). Heat a large skillet over medium heat. Cook the sandwiches to the pan. Cook, flipping once, until both sides are golden brown, about 4 minutes per side. Transfer to the prepared baking sheet with the bread bowls. Transfer the baking sheet to the oven to keep the grilled cheese sandwiches warm and melt the cheese inside the bread bowls, about 4 minutes. To serve, ladle the soup into the bread bowls and serve with the grilled cheese on the side. Garnish with parsley.