Homemade Basil Pesto and Cheddar Grilled Cheese with Creamy Classic Tomato Soup
 
 
Grilled cheese sandwiches stuffed with homemade basil pesto and cheddar cheese are served with a creamy tomato soup in this comfort food classic.
Yield: 4 servings
Ingredients
For the tomato soup
  • 1 tbsp unsalted butter
  • 1 tbsp olive oil
  • 1 onion, thinly sliced
  • 3 garlic cloves, smashed
  • 2 (28 oz) cans whole peeled tomatoes
  • 1 cup water
  • ⅔ cup heavy cream
  • 2 tsp kosher salt, plus more to taste
  • ¼ tsp freshly ground black pepper
  • ⅛ tsp red pepper flakes
  • ¼ tsp dried oregano
  • 1 tbsp sugar
For the grilled cheese
  • 3 cups loosely packed fresh basil leaves
  • 2 tbsp pine nuts
  • 1 garlic clove
  • 1 tsp lemon juice
  • 5 tbsp extra virgin olive oil
  • 3 tbsp grated Parmesan cheese
  • ½ tsp kosher salt, plus more to taste
  • 8 slices rustic bread, cut about ½-inch thick
  • 8 oz cheddar cheese, grated
  • butter, for greasing the pan
Instructions
For the soup
  1. Heat the butter and olive oil in a large heavy-bottomed pot over medium heat. Once the butter is melted, add the onion and garlic to the pan. Saute until the onion is tender and translucent, about 5 minutes. Add the tomatoes, water, cream, salt, red pepper flakes, oregano, and sugar. Bring to a boil and then lower the heat to simmer for 15 minutes.
  2. Remove the pot from the heat and puree with either an immersion blender or in the bowl of a tabletop blender. Season to taste with salt and black pepper. Serve warm.
For the grilled cheese
  1. To make the pesto, combine the basil, pine nuts, garlic, and lemon juice together in the bowl of a food processor. Pulse until smooth. Slowly pour in the olive oil while the processor is still running. Add in the parmesan cheese and pulse again to combine. Season to taste with salt.
  2. Place the bread slices on a work surface. Spread the prepared pesto over the top of half of the slices. Divide the cheese among the pesto-topped slices and then top with the remaining 4 slices of bread.
  3. Heat a grill pan or skillet over medium heat. Grease with butter. Add the sandwiches to the skillet and cook until the bottom side is brown, about 3 minutes. Flip and brown the other side, another 3 minutes. When both sides are brown and the cheese is melted, remove from the skillet and serve warm with the tomato soup.
Notes
Recipe from The Dahlia Bakery Cookbook: Sweetness in Seattle
Recipe by Joanne Eats Well With Others at https://joanne-eatswellwithothers.com/2017/03/homemade-basil-pesto-cheddar-grilled-cheese-creamy-classic-tomato-soup.html