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Chef's Tip
For the perfect grilled cheese, spread softened butter all the way to the edges of the bread, and cook low and slow to ensure the cheese melts completely while the bread develops a golden-brown exterior without burning.
Instructions
- For the tomato soup: Heat olive oil in a large pot over medium heat. Add onion, garlic, carrots, and celery. Cook until vegetables are softened, about 5-7 minutes.
- Add tomato paste and cook, stirring constantly, for 1 minute to caramelize slightly.
- Add canned tomatoes with their juice, breaking them up with a wooden spoon. Add broth, dried basil, oregano, bay leaf, salt, and pepper.
- Bring to a simmer, then reduce heat to low and cook, uncovered, for 20 minutes, stirring occasionally.
- Remove bay leaf. Use an immersion blender to purée the soup until smooth (or transfer in batches to a regular blender, being careful with the hot liquid).
- Stir in heavy cream and taste for seasoning, adding sugar if needed to balance acidity. Keep warm over low heat.
- For the grilled cheese: Butter one side of each bread slice, making sure to spread butter all the way to the edges.
- Heat a large skillet or griddle over medium-low heat.
- Place 4 bread slices butter-side down on the skillet. Top each with 2 slices of American cheese, then cover with remaining bread slices, butter-side up.
- Cook until bottom is golden brown, about 3-4 minutes. Flip carefully and cook until second side is golden and cheese is completely melted, about 2-3 minutes more.
- Cut each sandwich diagonally and serve immediately with hot tomato soup.
Plating
Ladle the creamy tomato soup into a wide, shallow bowl. Place the grilled cheese sandwich, cut diagonally into triangles, on a small plate alongside or partially resting on the edge of the soup bowl. Garnish the soup with a sprinkle of fresh basil chiffonade and a light drizzle of cream. For an extra touch, place a small grilled cheese 'dipper' (an additional small strip of sandwich) across the bowl.
Storage & Reheating
Tomato soup can be stored in an airtight container in the refrigerator for up to 4 days or frozen for up to 3 months. Reheat gently on the stovetop, adding a splash of broth or water if needed to adjust consistency. Grilled cheese sandwiches are best prepared fresh, as they lose their texture when stored.
About This Recipe
A quintessential American comfort food pairing that evokes childhood nostalgia for many. This diner classic combines the simple pleasure of melted cheese on toasted bread with the soothing warmth of tomato soup. The version elevates the humble tomato soup with the addition of aromatics and a touch of cream, while keeping the grilled cheese authentically straightforward with perfectly melted American cheese.