This can also be made vegetarian by using all vegetable stock, could also be vegan by replacing butter with something.
3 pounds tomatoes
Extra-virgin olive oil
3 tablespoons unsalted butter
1 small sweet onion, coarsely chopped
1 small carrot, coarsely chopped
1 small fennel bulb, coarsely chopped
4 cloves garlic, coarsely chopped
2 tablespoons Herbsaint, Pernod or other anise liquor
2 to 3 cups chicken or vegetable stock
5 sprigs fresh thyme
1 large sprig fresh basil
1 cup heavy cream (optional, you can just add more stock if you don't like cream)
Salt and freshly ground black pepper to taste
Heat oven to 400F. Cut the tomatoes in half crosswise and use your fingers to clean out the seeds. Place the cut tomatoes on a foil-lined baking sheet, drizzle with olive oil and toss to lightly coat tomatoes. Then, place tomatoes cut side down on the baking sheet and roast for 35-45 minutes, until they are very soft and the skins are starting to darken. Remove from the oven and let cool. Remove the skins, they should slip off easily.
Melt butter in a large saucepan over medium heat and sauté the chopped onions, carrot, garlic and fennel for a minute or 2, turn down heat to medium low and cook until they are soft, about 12 minutes, stirring occasionally. Add 2 cups of stock and the fresh herbs. Simmer over low heat for 30 minutes. Remove the herb sprigs (you can leave the basil leaves ((remove stem)) if you want). Add the roasted tomatoes (I take out the stem end) and Pernod to the pan. Using an immersion blender, a countertop blender, food processor, or food mill, puree until smooth. Add the cream (or up to a cup or so of stock), some salt and pepper, and return the soup to a simmer. If the soup is too thick, thin it with more stock. Taste, adjust seasoning, and keep warm over low heat until ready to serve.
Besides grilled cheese sammies, you can make cheese croutons like you would with French onion soup, or make a thick aioli, add some cheese, spread on toasted bread slices, then toast until lightly browned.