Strain tomatoes, reserving the juices, and spread onto a baking sheet. Season with salt and pepper to taste then drizzle ¼ cup olive oil. Roast until caramelized, about 15 minutes.
Meanwhile, heat olive oil over medium-low heat. Add the celery, carrot, onion and garlic, cook until softened (about 10 minutes). Add the roasted tomatoes, tomato juices, red pepper flakes, chicken broth, bay leaf and butter. Simmer until vegetables are tender (about 15-20 minutes). Add basil or parsley and cream. The heavy cream is optional an you can start with 1/4cup and more based on your preference. Puree using a hand held immersion blender until smooth.
For the grilled cheese croutons:
butter your butter and grill. Place two slices of cheese in between your bread. Heat until cheese is melted.