Roasted Tomato Basil Soup w/ grilled cheese croutons

This is one of those soups that just brings back my childhood, only this is better.  Did you ever as a kid have tomato soup and a grilled cheese sandwich?  I would always dunk my sandwich in the soup.  It's just one of those natural combinations that is oh so good.  With this soup what I love to do is cut up my grilled cheese into croutons and float it in the soup, it is marvelous.  If you really want to go to the next level with the sandwich, get some good sourdough bread and different cheeses and grill away. Cut the sandwich into croutons and enjoy.

Roasted Tomato Basil Soup

3 lbs. ripe tomatoes, halved with seeds scooped out
1/8 cup plus 2 tablespoons olive oil
1 tablespoon salt
1 1/2 teaspoons black pepper
2 teaspoons butter
1 onion, chopped
5 cloves garlic, minced
1/2 teaspoon red pepper flakes (optional)
2 - 14.5 oz. cans stewed tomatoes
fresh basil leaves, a handful or packed cup, chopped
1 teaspoon fresh thyme leaves
4 cups low-sodium chicken stock


Preheat oven to 400 degrees.  Combine the tomato halves, 1/8 cup olive oil, salt and pepper in a large bowl; toss well to coat the tomatoes.  Spread the tomato halves out on a large baking sheet.  This should be a heavy baking sheet otherwise you may get smoking from the pan and olive oil.  Roast the tomatoes for 45 minutes.

In a large stockpot or Dutch oven over medium heat, combine the remaining 2 tablespoons of olive oil with the butter and heat until the butter is melted.  Add the onions, garlic and red pepper flakes to the pot and cook,  stirring occasionally, until softened, about 7-10 minutes.  Add in the stewed tomatoes, roasted tomatoes, basil, thyme and chicken stock.  Bring the mixture to a boil.  Lower the heat and simmer, uncovered 40 minutes.

Use an immersion blender to puree the soup until completely smooth.  (Alternatively, you can use a blender or food processor.  If you do, be sure to vent the steam and be every careful not to spill the hot liquid or wait until it cools down a little)