Close-up of Grilled Cheese and Broiled Tomato Soup, as seen on The Pioneer Woman, season 34.
Recipe courtesy of Ree Drummond

Grilled Cheese and Broiled Tomato Soup

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  • Level: Easy
  • Total: 16 min
  • Active: 16 min
  • Yield: 2 servings
This is a spin on a classic comfort pairing. Ree’s broiled tomatoes makes for an easy, hands-off preparation that also intensifies their flavor. It is a good idea to make a big batch, as it keeps well in the fridge or the freezer.



Grilled Cheese:


  1. For the soup: Preheat the oven to broil. Heat a large cast-iron skillet or griddle over medium heat.
  2. Add the tomatoes, tomato paste, green onions and garlic to a small baking dish. Drizzle over the olive oil and sprinkle with salt and pepper. Toss to combine, then place under the broiler to lightly char the tomatoes and cook the tomato paste, about 6 minutes.
  3. Shake the baking dish, then add the cream, balsamic and rosemary. Return to the broiler and cook until the cream has reduced and thickened slightly, an additional 6 to 7 minutes.
  4. Add the tomato mixture to a heatproof blender and puree until smooth. Taste and adjust the seasoning. Divide between two bowls, swirling a tablespoon of pesto into each.
  5. Meanwhile, build the grilled cheese sandwiches by laying out the bread. Spread a tablespoon of pesto on each slice of bread. For each sandwich, lay 2 pieces of American cheese, half the grated Gruyère, then 2 more slices of American cheese on one of the slices. Top with the remaining slices of bread. Spread 1 tablespoon of mayonnaise on the top of each. Place in the skillet, mayo side down. Spread the top of the sandwiches with another tablespoon of mayonnaise each. Toast, flipping as needed, until the cheese has melted on the inside and the outside is golden, 4 to 5 minutes a side. Serve with the soup.