There are grilled cheese sandwiches, and then there are grilled cheese sandwiches. The difference usually comes down to one decision made early: are you using the right cheese, or are you using whatever’s in the fridge?
This version starts with pimiento cheese — the Southern staple that somehow never gets old — made from scratch with extra-sharp cheddar, roasted red peppers, Duke’s mayonnaise, and just enough cayenne to remind you it’s there. Paired with a roasted tomato soup that earns its depth from 45 minutes in a hot oven rather than from a can, this is the kind of meal that justifies owning a cast iron skillet.
A few things make this combination work better than the standard version.
On the pimiento cheese: Grate your own cheddar. Pre-shredded cheese contains anti-caking agents that dull the flavor and affect the texture of the spread. It takes three extra minutes and makes a real difference. The same logic applies to draining your pimentos thoroughly — excess liquid is the enemy of a good spread.
On the grilling: Mayo on the outside of the bread instead of butter. It sounds wrong and it isn’t. Mayo has a higher smoke point, browns more evenly, and won’t burn on the edges before the center catches up. Use it thin and complete — every inch of crust covered. A lid on the skillet traps heat and melts the cheese from the top while the bottom browns, which solves the age-old problem of a golden exterior and a cold, unmelted center.
On the soup: Roasting the tomatoes, onion, and garlic at 425°F before blending is what separates this from every other tomato soup. The oven does the work of caramelizing and concentrating the flavor that stovetop cooking can’t replicate in the same way. Pull the garlic cloves out of their skins once they’re cool enough to handle — they’ll be soft, sweet, and deeply savory. Run the blended soup through a strainer if you want an extra-silky finish, though it’s good either way.
The two recipes are designed to be made together, with the soup roasting while you prep the pimiento cheese spread — which benefits from an hour in the refrigerator anyway to let the flavors come together. By the time the soup is blended and simmering, you’re ready to grill.
It’s Southern comfort food made with a little more intention than usual. Which, as it turns out, is usually all it takes.
PIMIENTO CHEESE GRILLED CHEESE & ROASTED TOMATO SOUP
A Southern comfort food combination worth making right — homemade pimiento cheese on sourdough, paired with a deeply roasted tomato soup. Serves 4.
PIMIENTO CHEESE SPREAD
8 oz extra-sharp cheddar block, hand-grated 4 oz jarred roasted red peppers (pimentos), drained and finely diced ⅓ cup Duke’s mayonnaise (or Hellmann’s) 1 tsp Worcestershire sauce ½ tsp yellow mustard ¼ tsp garlic powder ¼ tsp onion powder ¼ tsp cayenne pepper Fresh cracked black pepper to taste
GRILLED CHEESE
8 thick slices sourdough bread 2 tbsp mayonnaise (for the outside of the bread)
ROASTED TOMATO SOUP
3 lbs ripe tomatoes (Roma or heirloom), halved 1 large yellow onion, cut into thick wedges 6–8 garlic cloves, unpeeled ⅓ cup extra-virgin olive oil Kosher salt & freshly ground black pepper 2 cups low-sodium chicken or vegetable broth ½–¾ cup heavy cream 2–3 tbsp unsalted butter ½ cup fresh basil leaves, torn
INSTRUCTIONS
1. Make the pimiento cheese spread Grate the cheddar on the fine side of a box grater — fine shreds give a creamier spread. Pat the pimentos completely dry with paper towels. In a bowl, mix the mayo, Worcestershire, mustard, garlic powder, onion powder, cayenne, and black pepper until smooth. Fold in the cheddar and pimentos gently. Don’t overmix — keep some texture.
2. Chill the spread Cover and refrigerate for at least 1 hour to let the flavors meld.
3. Roast the vegetables Preheat oven to 425°F (220°C). On a large rimmed baking sheet, arrange the tomatoes cut-side up with the onion wedges and unpeeled garlic cloves. Drizzle with olive oil and season generously with salt and pepper. Roast 35–45 minutes until everything is caramelized and jammy.
4. Blend the soup Once cool enough to handle, squeeze the garlic out of their skins. Transfer everything from the pan — including all juices and oil — to a blender. Add the broth and blend until completely smooth. For an extra-silky texture, pass through a fine mesh strainer.
5. Finish the soup Pour the purée into a pot over medium heat. Stir in the cream starting with half and adding more to taste, then add the butter. Simmer gently 5–10 minutes. Taste and adjust salt, pepper, and acid (a small splash of sherry vinegar or balsamic brightens it if needed). Stir in most of the basil just before serving.
6. Assemble the sandwiches Spread the pimiento cheese thick on the inside of the bread. Spread mayo thinly but completely on the outside of both slices — it browns more evenly than butter and won’t burn at the edges.
7. Grill the sandwiches Preheat a dry cast iron skillet over medium-low heat for 2 minutes. Place the sandwich in the skillet and cover with a lid. Cook 3–4 minutes until the bottom is deep golden.
8. Flip and finish Flip the sandwich, cover again, and cook another 3–4 minutes. Press gently with a spatula for even contact. If cheese isn’t fully melted, reduce heat to low, cover, and cook 1–2 more minutes. Pro trick: after flipping, sprinkle a pinch of grated cheddar directly into the skillet around the edges — it fries into lacy cheese frico that sticks to the crust.
9. Rest and serve Let the sandwich rest 60 seconds before slicing diagonally. Ladle the soup into bowls, drizzle with olive oil, scatter the remaining basil, and add freshly cracked black pepper. Serve immediately.
NOTES Grate your own cheddar — pre-shredded contains anti-caking agents that dull the flavor. The soup can be made ahead and reheated; the flavor improves overnight. For dairy-free, substitute full-fat coconut milk for the heavy cream.
