Ingredients

2 tbsp. extra-virgin olive oil

1 small yellow onion, finely diced (about 1 1/4 c.)

2 garlic cloves, minced

kosher salt

Black pepper

1 28-oz. can whole, peeled tomatoes, with juices

1 28-oz. can chopped fire-roasted tomatoes, with juices

1/2 c. chopped basil, divided, plus more for garnish

2 tbsp. sugar

1 tbsp. balsamic vinegar

1/3 c. heavy cream or half-and-half, plus more for garnish

8 slices sourdough Pullman-style bread

8 oz. sharp white cheddar, grated (about 2 cups)

Preparation

Step 1In large pot, heat 1 tablespoon olive oil over medium-high heat. Add onion and garlic and cook until soft, 4 minutes. Season with salt and pepper.Step 2Add tomatoes and juices, gently crushing whole tomatoes with a wooden spoon. Add 2 cups water, ¼ cup basil, and sugar; bring to boil.Step 3Reduce heat to low and simmer, partially covered, until thickened slightly, 20 minutes. Stir in balsamic vinegar, remaining ¼ cup basil, and season with salt and pepper.Step 4If you have an immersion blender, puree soup in pot. (Otherwise, carefully transfer about half of soup into blender. Remove hole on top (to let steam escape) and cover with a dishtowel you don’t mind getting dirty. Press down firmly on lid and pulse mixture several times, gradually increasing speed to high. Puree until smooth, then transfer to clean pot. Puree remaining tomato mixture and transfer to new pot. Stir in cream, over medium heat, and bring to simmer. Remove from heat and cover with lid.Step 5Heat panini press. (If you don’t have a panini press, use a nonstick grill-pan or cast iron skillet over medium-high heat.) Grease surface of press or pan with remaining tablespoon of olive oil. Arrange 4 slices bread on a clean work surface. Place ½ cup cheese on each slice of bread and cover with remaining slices.Step 6Cook sandwiches, until cheese has melted and bread is crisp and golden brown, about 4 minutes. (If you’re using grill pan or cast iron skillet, place another heavy skillet on top of sandwiches to press while they’re cooking; flip once halfway through.) Cut each sandwich into 4 squares.Step 7Ladle soup in bowls, drizzle with a bit of cream (stir it in so it creates a pretty pattern), and garnish with basil leaves. Serve with grilled cheese bites on the side.

Why tomato soup and grilled cheese? The idea behind the pair came from a few angles. Grilled cheese was a common item during World War 1 feeding soldiers on base. And, once the recession hit schools were serving cheese toast and tomato soup as a way to maintain the daily nutrition recommendation. This was an all around simple and affordable meal.  Types of tomatoes to use Tomatoes are the entire base of the recipe so it’s important to use a top quality variety. San Marzanos have the skin to flesh to seed ratio often boasted about. Campari tomatoes, cherry or grape tomatoes, and beefsteaks are other types that could be used in conjunction with one another. If you can use fresh tomatoes in soup then your result will be slightly different than a canned variety. Either is fine just make sure you’re getting the best stuff.  What else goes well with tomato soup? Tomato soup doesn’t have to be eaten solely with a spoon. You could use it to dunk mozzarella sticks or crusty buttered bread into. Chicken quesadillas or an arugula salad would make great additions.  Could I add other components to tomato soup?Think about what you would want in any soup. Pasta shells or ditalini could be lovely here. Shrimp or pieces of spicy Italian sausage would make this well rounded with protein. Peas, spinach, or escarole would give that much needed veggie punch. Made this recipe? Let us know in the comments below! Editor’s Note: This recipe was updated on August 8, 2022.