Entree Recipes

Double Stuffed Grilled Cheese

Double Stuffed Grilled Cheese

Double Stuffed Grilled Cheese

I used to wonder why people would create sandwiches that took as much time and/or effort as a regular entree. I thought sandwiches were meant to be quick and easy. Boy was I wrong. After creating what I will call the Double Stuffed Grilled CheeseĀ that we had for dinner tonight, I can appreciate why one would go through extra efforts on a sandwich; specifically, a grilled cheese sandwich.

I debated calling these babies Double Stuffed Grilled Cheese with Chiles, but I didn’t want people browsing through, to think these sandwiches might be hot, and pass on by. While this sandwich has a few different peppers and/or chiles, do not let that fool you into thinking this is a spicy or hot sandwich. This grilled cheese simply has a lot of great flavor and body to it. Trust me – my dad doesn’t do spicy, but he sure enjoyed this sandwich! The picture doesn’t really do it justice as I didn’t have my nice camera with me, but I will be making this again Fo’ Sho!

This recipe is adapted and altered from Serious Eats. I hope you will give it a try, and enjoy it. Eat as is or add a side of something cool and refreshing.

5.0 from 3 reviews
Double Stuffed Grilled Cheese Sandwich
Prep time: 
Cook time: 
Total time: 
Serves: 6
  • 1 Tbs olive oil
  • 2 anaheim chiles, split in half, stems, seeds, and ribs removed
  • 2 red jalapeno peppers, split in half, stems, seeds, and ribs removed
  • 6 Tbs mayonnaise, divided
  • 2 Tbs finely grated yellow or white onion
  • 2 medium cloves garlic, minced (about 2 teaspoons)
  • 1 Tbs Dijon mustard
  • ½ tsp ground cumin
  • 1 small can chopped olives
  • ½ diced red bell pepper
  • 2 Tbs diced sun dried tomatoes
  • 2 Tbs fresh basil, chopped (I cut with scissors)
  • 4 oz cream cheese, softened
  • 2 tsp Worcestershire sauce
  • 2 cups grated extra-sharp white cheddar cheese
  • Kosher salt and freshly ground black pepper
  • 8 (1/2-inch thick) slices country-style bread
  1. Heat oil in large skillet over medium-high heat until shimmering. Add chiles jalapeno peppers, and cook. Turn once halfway through cooking, reducing heat if threatening to burn, until spotty black and softened, about 10 minutes.
  2. Transfer to cutting board. When cool enough to handle, finely chop chiles and set aside. Wipe out skillet with paper towel.
  3. Melt 2 Tbs mayonnaise in empty skillet, over medium heat. Add onion and cook, stirring, until onion is softened, about 2 minutes. Add garlic, mustard, and cumin and cook until fragrant, about 30 seconds. Transfer to bowl with and let cool to room temperature, about 5 minutes.
  4. To onion mixture, stir in olives, red bell pepper, sun dried tomatoes, chopped chiles and jalapenos, basil, cream cheese, Worcestershire, cheese, and additional 2 Tbs mayonnaise. Season to taste with salt and pepper.
  5. Brush one side of each slice of bread with remaining 2 Tbs mayonnaise, then flip.
  6. Spread a heaping ¼ cup of spread on 6 slices bread and cover with remaining 6 slices, mayonnaise-spread sides facing up.
  7. Heat skillet over medium heat. Cook sandwiches until golden and beginning to ooze cheese, 2 to 3 minutes per side. Transfer sandwiches to cooling rack and allow to rest 2 minutes before cutting. Cut in half and serve.

Double Stuffed Grilled Cheese

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Emily Buys


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