Classic Grilled Cheese with Creamy Tomato Soup

Start the Soup Base

Heat olive oil in a large pot over medium heat.

Add the diced onion and cook, stirring occasionally, until softened and translucent, about 5 minutes.

Add the minced garlic and cook for 1 minute, stirring constantly, until fragrant.

Build the Soup

Pour in the crushed tomatoes and vegetable broth.

Add the sugar, dried basil, oregano, salt, and black pepper.

Stir everything together to combine.

Bring the soup to a boil, then reduce the heat to low and simmer uncovered for 15 minutes.

Blend the Soup

Remove the pot from the heat.

Use an immersion blender to blend the soup until completely smooth, about 30 seconds.

Return the pot to low heat.

Pour in the heavy cream and stir gently to combine.

Taste the soup and adjust salt and pepper as needed.

Keep the soup warm on low heat while you make the grilled cheese sandwiches.

Assemble the Grilled Cheese

Lay all 8 slices of bread on a clean surface.

Spread softened butter evenly on one side of each bread slice.

Flip 4 slices over so the butter side faces down.

Place 2 slices of American cheese and 1 slice of cheddar on each of those 4 slices.

Top each with a remaining bread slice, butter side facing up.

Cook the Grilled Cheese

Heat a large skillet or griddle over medium-low heat.

Place 2 sandwiches in the skillet and cook until the bottom is deep golden brown, about 3–4 minutes.

Flip each sandwich carefully using a spatula.

Cook the second side until golden brown and the cheese is fully melted, about 3 minutes more.

Transfer the cooked sandwiches to a cutting board.

Repeat with the remaining 2 sandwiches.

Serve

Cut each sandwich diagonally in half.

Ladle the tomato soup into 4 bowls.

Garnish each bowl with fresh basil chiffonade.

Serve each bowl alongside a grilled cheese sandwich and enjoy immediately.