Roasted Tomato Soup and Grilled Cheese Bread Bowl

Save on dishes while bringing together two things that should never be apart — grilled cheese and tomato soup.


  • For the roasted tomato soup:
  • 1/4 cup extra-virgin olive oil, divided
  • 2 pounds heirloom tomatoes, cored and quartered
  • 3 cloves garlic, peeled and smashed
  • 1/2 yellow onion, cut into 2-inch wedges
  • 1 teaspoon kosher salt
  • 1 teaspoon freshly ground black pepper
  • 1 cup low-sodium chicken stock
  • 3 sprigs fresh thyme
  • 2 teaspoons raw cane sugar
  • 2 tablespoons unsalted butter
  • 3 tablespoons heavy cream
  • For the bread bowl:
  • 1 large (2-pound) loaf rustic sourdough bread
  • 4 tablespoons unsalted butter, melted
  • 1 clove garlic, grated
  • 1 tablespoon chopped parsley leaves
  • 1 tablespoon grated Parmesan cheese
  • 7 slices Colby Jack cheese (can be substituted for any desired cheese)


  1. Make the roasted tomato soup:
  2. Preheat oven to 400 degrees F, and coat a large-rimmed baking sheet with half of the olive oil.
  3. Evenly distribute the tomatoes, garlic and onions onto the prepared pan, drizzle with remaining olive oil and season with salt and pepper. Roast for 30 to 40 minutes until the tomatoes and onions have caramelized and softened.
  4. Transfer the contents of the sheet tray to a large cast-iron or heavy-bottomed pot.
  5. Add chicken stock, thyme, sugar and butter and bring to a boil. Reduce heat to a simmer and cook uncovered, stirring occasionally, for 20 minutes or until liquid has reduced by a third. Add the cream, and blend using an immersion blender until the soup is silky and smooth. Strain, if desired. Continue to simmer the soup for another 10 minutes until thickened.
  6. Bake the bread bowl:
  7. Reduce oven temperature to 350 degrees F, and prepare a large-rimmed baking sheet with parchment paper.
  8. Cut a 4 to 5-inch square out of one end of the bread loaf and hollow out the inside, leaving about 1 inch of bread on all sides. Cut 6, 1-inch vertical slices into the other half of the loaf making sure not to cut all the way through. Transfer the loaf to the prepared baking sheet.
  9. In a small bowl, combine the melted butter, garlic and parsley. Using a pastry brush, brush the mixture over the surface of the sliced bread loaf.
  10. Place the cheese slices between all vertical slices of bread and into the bottom of the hollowed out well. Sprinkle the whole loaf with Parmesan cheese and bake until the cheese has melted and the loaf is golden brown, about 10 minutes.
  11. Ladle the roasted tomato soup into the cheese-lined well and serve immediately.