Classic Cream Of Tomato Soup

Make sure to use canned whole tomatoes that are not packed in puree; you will need some of the juice to make the soup.

1. Adjust oven rack to upper-middle position and heat oven to 450 degrees. Spread tomatoes in single layer over aluminum foil–lined rimmed baking sheet and sprinkle evenly with brown sugar. Bake until all liquid has evaporated and tomatoes begin to color, about 30 minutes. Let tomatoes cool slightly, then peel them off foil and transfer to small bowl.
2. Melt butter in medium saucepan over medium heat. Add shallots, tomato paste, and allspice. Reduce heat to low, cover, and cook, stirring occasionally, until shallots are softened, 7 to 10 minutes. Add flour and cook, stirring constantly, until thoroughly combined, about 30 seconds. Whisking constantly, gradually add chicken broth. Stir in reserved tomato juice and roasted tomatoes. Cover, increase heat to medium, and bring to boil, then reduce heat to low and simmer, stirring occasionally, to blend flavors, about 10 minutes.
3. Strain mixture into medium bowl and rinse out saucepan. Transfer tomatoes and solids in strainer to blender. Add 1 cup strained liquid to blender and puree until smooth. Add remaining strained liquid.
4. Return the pureed mixture to the saucepan, stir in cream, and heat over low heat until hot, about 3 minutes. Off heat, stir in brandy. Season with salt and cayenne to taste. Serve immediately.
   MAKE-AHEAD: Soup can be prepared through step 3 and refrigerated for up to 3 days or frozen for up to 2 months. Reheat over low heat before proceeding with step 3.