Transfer the veggies to a pot (or a blender, if you’re not using an immersion blender). Scrape all the liquid into the pot as well. That liquid is bursting with flavor, and is very important for building layers of flavor in your soup.
Transfer the pot to the stove and heat over medium heat just until boiling, stirring occasionally. Add salt and pepper to taste. Stir in half & half at this point, if using, for extra creaminess and body.
Over medium heat, warm a nonstick skillet, then place one slice of bread in the skillet, buttered side down. Evenly layer 2 pieces of sharp cheddar cheese and 2 pieces of provolone cheese. Top with another slice of bread, buttered side up this time. Let the bread get all toasty and golden brown (like pictured above), then flip to toast the other side. If your skillet is on medium heat, the cheese should be completely melted by the time both sides of your sandwich are toasted.
Tomato Soup and Grilled Cheese Sandwiches
3/8 cup olive oil
2 ½ lbs tomatoes (about 8 medium)
1 medium onion
3 garlic cloves
¾ tsp salt
1 ½ Tablespoons tomato paste
12 basil leaves
2 cups chicken broth
2 Tbsp Half & Half, optional
8 slices potato sandwich bread
Softened butter, for spreading
8 slices sharp cheddar cheese
8 slices provolone cheese
For the soup: Preheat oven to 425°F. Pour oil onto a baking sheet. Slice tomatoes in half, and arrange on baking sheet, cut side down. Cut onion into eighths, and place on baking sheet. Peel garlic cloves, but leave whole, and place on baking sheet. Roast in the preheated oven for 35 minutes, until tomatoes are blistered and onions and garlic are soft.
Transfer all roasted vegetables to a pot, then scrape all leftover oil into the pot. Add the salt, tomato paste, and basil leaves. Puree with an immersion blender (or blend in a blender) until no chunks are present. Add chicken broth and puree until smooth. Transfer the pot to the stove and heat over medium heat just until it comes to a boil, stirring occasionally. Add salt and pepper to taste. Stir in Half & Half if using.
For the sandwiches: Butter one side of each piece of bread with softened butter. Heat a nonstick skillet on medium heat. Place one piece of bread in the skillet, buttered side down. Top with 2 slices sharp cheddar and 2 slices provolone. Top with another piece of bread, buttered side up. Cook sandwich 3-4 minutes, until the bread is golden brown. Flip sandwich, and cook 3-4 more minutes, until bread is toasted and cheese is melted. Slice in half and serve immediately.