|2 (28 ounce) cans whole tomatoes (not packed in puree), drained, 3 cups juice reserved|
|1-1/2 tablespoons brown sugar|
|4 tablespoons unsalted butter|
|4 large shallots , minced|
|1 T. tomato paste|
|Pinch ground allspice|
|2 T. all-purpose flour|
|1-3/4 cups chicken stock|
|1/2 cup heavy cream (or half-and-half or milk)|
1. Adjust oven rack to upper-middle position and heat oven to 450 degrees; line jelly-roll pan or rimmed cookie sheet with foil. Spread tomatoes in single layer on foil, 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; transfer to small bowl and set aside.
2. Heat butter over medium heat in medium nonreactive saucepan until foaming; 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 stock; stir in reserved tomato juice and roasted tomatoes. Cover, increase heat to medium, and bring to boil; reduce heat to low and simmer, stirring occasionally, to blend flavors, about 10 minutes.
3. Strain mixture into medium bowl; rinse out saucepan. Transfer tomatoes and solids in strainer to blender; add 1 cup strained liquid and puree until smooth. (You can also use a Cuisinart or similar appliance. I use an immersion blender and puree the soup right in the pot.) Add remaining reserved liquid.
4. Return the pureed mixture to the saucepan, add cream, and heat over low heat until hot, about 3 minutes. Off heat, stir in brandy or sherry; season to taste with salt and cayenne, and serve immediately.