for the grilled cheese – using a rolling pin, flatten bread squares to 1/4 inch thickness. Place a cheese slice on top of each slice of bread, then roll up tightly. Melt 2 tablespoons butter in a large skillet over medium high heat. Working in batches, add roll ups to the skillet, cooking until all sides are golden brown and the cheese has melted, about 3-4 minutes, adding more butter as needed.
for the tomato soup – Heat a medium saucepan over medium-low heat and add the butter. Add in the shallots and garlic, cooking until soft and slightly golden, stirring occasionally for 8-10 minutes. Stir in the tomato paste and cook for another 5 minutes. Add in the tomatoes, sherry, chicken stock, brown sugar, basil, salt and pepper, then bring the mixture to a boil. Reduce to a simmer and cook for 20 minutes.
Transfer the soup to a high-powered blender and carefully blend until pureed or your desired consistency is reached. Transfer back to the pot over low heat. Right before serving, stir in the heavy cream. Taste and season additionally with salt and pepper if needed. To serve, garnish with freshly grated cheese and fresh herbs.