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Pimento Grilled Cheese with Bacon

Featuring Pimento grilled cheese sandwich with bacon and homemade pickles.

Indulge with an irresistible Pimento Grilled Cheese, loaded with bacon, homemade pickles, and jalapenos. This creamy and crispy sandwich comes together quickly and disappears just as fast.

Double pimento grilled cheese sandwiches, ready to be sliced.

Even adults need their grilled cheese! Loading this up with the Jalapeno Pimento Cheese and crispy bacon transforms it into much more.

Why This Recipe Works

One Pan Meal – Get out your skillet, and that’s all you will need. Everything comes together in minutes, especially if you’re firing it up on the grill.

Quick Fire – Once the grill is heated up, this sandwich comes together in less than 15 minutes. Start with the bacon and have everything else ready to swap out.

Textures and Flavors – Between slices of crusty artisan bread is rich, melty pimento cheese, crispy smoked bacon, and vibrant crunchy pickles. You don’t need sauce, lettuce, or anything else to get an explosion of flavor in your mouth.
Sliced and stacked pimento grilled cheese.

Grilling Cheese Sandwiches

This recipe can easily be made in any pan, whether it’s on the grill or over the stovetop.

Grilling sandwiches really adds wood-fired flavor, even if you use cast iron. The smoke wafts all around the food while the coals are burning. If you use a lid with the vents open, it can add even more flavor while the bacon is cooking and the sandwich is toasting.

Try using a griddle or a flattop if you don’t have a grill or cast iron skillet. The larger surface also allows you to make many more sandwiches as well.

Ingredients Needed

This pimento grilled cheese doesn’t require many ingredients, but they are all high-quality choices:

  • Artisan Bread – Go for sourdough, country loaf, or any flavor that you’d prefer. Artisan bread is a must, providing you that crusty outside with a soft, but structural center. Keep the Wonder bread for your American cheese slices.
  • Pimento Cheese – Storebought or homemade, just get some. We obviously have a delicious, simple recipe for Jalapeno Pimento Cheese (which you should absolutely prepare) that works perfectly with this recipe.
  • Pickles – Anything with some acid helps to cut through the fatty flavors and brighten up each bite. If you are seeking something homemade and delicious, try the Sweet and Spicy Pickles, or kick it up further with Smoked Pickled Jalapenos. Either way, it’ll be delicious.
  • Bacon – Thick-cut bacon is the best, but any crispy bacon will do. Go for the peppered bacon at the butcher for a bold bite.
Cook the bacon in cast iron over the coals until crispy.

Step 1: Cook Bacon

Heat up your grill to medium-high heat. Add wood chips or chunks for additional flavor. Yes, the smoke from the wood absolutely flavors the food, even with a cast iron skillet.

Place your cast iron skillet over the coals and add the bacon immediately. Don’t go anywhere, you’ll need to flip the bacon a few times to ensure it cooks evenly. Have a plate with a paper towel nearby to set the bacon when it’s crispy.

Toast the artisan bread in the bacon fat first, these will be the sandwich tops.

Step 2: Toast the Top Slices

Once the bacon is out of the skillet, place the top slices into the bacon fat and press down slightly. These will toast pretty quickly, so have a metal spatula nearby to fetch the bread.

It’s up to you as to whether you prefer to toast both sides or not. Personally, I only toast one side and remove them.

Step 3: Sear the Sandwich

Load up the bottom slice with pimento cheese, crispy bacon, and your choice of pickles. Carefully set the loaded slices of bread into the skillet.

Place the previously toasted top slice on the sandwiches and press down with your spatula. If you have a lid for the skillet, this is a good time to add it briefly, aiding the cheese melt.

The pimento grilled cheese will be toasted on the bottom within just a couple of minutes.

Close up shot of the delicious pimento grilled cheese, sliced to serve.

Variations for Toppings

This pimento grilled cheese is best served warm, right off the grill. Having a combination of the crispy bacon, the creamy pimento cheese, and the tangy pickles make for an incredibly satisfying sandwich.

Feel free to get creative with other meats or vegetables to pile in the sandwich. My only real advice is to keep it to two other fillings, outside of the pimento cheese. Other recommended toppings:

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Featuring Pimento grilled cheese sandwich with bacon and homemade pickles.

Pimento Grilled Cheese with Bacon

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Indulge with an irresistible Pimento Grilled Cheese, loaded with bacon, homemade pickles, and jalapenos. This creamy and crispy sandwich comes together quickly and disappears just as fast.

  • Total Time: 20 minutes
  • Yield: Serves 2-4 1x

Ingredients

Scale

Instructions

  1. Preheat your grill to medium-high heat. Have everything prepared and ready to go for cooking, this recipe comes together quickly.
  2. Place a cast iron skillet over the coals once preheated. Add the bacon right away, allowing it to cook as the skillet warms up. Flip every couple of minutes until the bacon is cooked to your desired crispness. Remove the bacon when ready and set it on a paper plate lined pine a paper towel.
  3. Add 2 slices of bread to the skillet, which will be the toasted tops to the sandwich. They will crisp up quickly, so check them after about 2 minutes, using a spatula. You can toast both sides if desired.
  4. Using the remaining 2 slices, divide up the pimento cheese and spread it on each slice. Add the bacon and pickles as desired. Place each slice in the skillet carefully to toast the bread. Add the toasted top slices to each sandwich, and gently press down.
  5. If you have a lid or a sandwich press, this helps to melt the cheese quickly.
  6. Check the bottom of the sandwiches after about 2 minutes, and remove when toasted to your preference.
  7. Remove from the skillet, slice, and serve!

Notes

  • This sandwich can be prepared on any griddle or flattop as well. If you don’t have a grill, you can easily make this on the stove.
  • Author: Brad Prose
  • Prep Time: 5 minutes
  • Cook Time: 15 minutes
  • Category: Burgers & Sandwiches
  • Method: Grilling
  • Cuisine: Sandwich
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