Sloppy Joe Grilled Cheeses

published May 26, 2022
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Sloppy Joe Grilled Cheeses Recipe

Sloppy joe filling gets the grilled cheese treatment for the ultimate saucy, crispy sandwich.

Serves4

Prep5 minutes

Cook40 minutes

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Credit: Christine Han; Food Styling: Pearl Jones

Sloppy Joes are one of my go-to weeknight meals using ground beef. They’re faster and easier than burgers, and offer up protein and veggies in a sauce that kids (and adults) love. In fact, you might argue that sloppy Joes don’t need improving. Yet, here I am asking you to do just that by adding two key ingredients to the mix: crispy bread and grilled cheese.

Why Sloppy Joe Grilled Cheeses Are Better than Sloppy Joes

The sloppy in their name implies that sloppy Joes will always be messy. That’s part of what makes them fun! But there’s messy and then there’s too messy — and saucy meat on a soft bun can lead to the latter. Luckily, there’s an easy, grilled cheese-inspired fix: Use a sturdier, crispier bread and secure the filling with cheese. Sloppy Joe grilled cheeses are far easier to eat and, dare I say, even more delicious than the original. 

Here, we’ve built the grilled cheeses with thick sourdough bread slices and sharp cheddar cheese, but feel free to experiment with other bread and cheese choices. Whatever you choose, you’ll cook the sandwiches up in a cast iron skillet until golden-brown and crispy — and wonder why you haven’t been making sloppy Joes into grilled cheeses all along. 

Sloppy Joe Grilled Cheeses Recipe

Sloppy joe filling gets the grilled cheese treatment for the ultimate saucy, crispy sandwich.

Prep time 5 minutes

Cook time 40 minutes

Serves 4

Nutritional Info

Ingredients

  • 4 tablespoons

    (1/2 stick) unsalted butter

  • 1 tablespoon

    olive oil

  • 1 pound

    lean ground beef

  • 1 teaspoon

    kosher salt

  • 1 teaspoon

    garlic powder

  • 1 teaspoon

    onion powder

  • 1/2 cup

    water

  • 1 tablespoon

    packed light or dark brown sugar

  • 1 teaspoon

    Worcestershire sauce

  • 8 slices

    sourdough bread (about 1/2-inch thick)

  • 4 cups

    shredded sharp cheddar cheese (1 pound), divided

Instructions

  1. Let 4 tablespoons unsalted butter sit at room temperature until softened.

  2. ​​Heat 1 tablespoon olive oil in a large skillet over medium heat until shimmering. Add 1 pound lean ground beef and cook until cooked through and browned. Season with 1 teaspoon kosher salt, 1 teaspoon garlic powder, and 1 teaspoon onion powder. Cook until fragrant, about 1 minute more.

  3. Add 1/2 cup water, 1 tablespoon packed brown sugar, and 1 teaspoon Worcestershire sauce. Stir to combine and cook until saucy. Remove the pan from the heat.

  4. Butter one side of 8 slices sourdough bread (1/2 tablespoon each). Flip 4 of the slices over. Sprinkle each with 1/2 cup shredded sharp cheddar cheese. Top each with 1/2 cup sloppy Joe mixture, then sprinkle each with another 1/2 cup of the cheese.

  5. Close the sandwiches with remaining bread slices buttered-side up. Heat a large skillet over medium-high heat. Cook 2 sandwiches at a time: Add to the pan and cook until golden-brown and cheese is melted, 4 minutes per side. Transfer to a cutting board and cut in half.

Recipe Notes

Make ahead: The sloppy Joe mixture can be cooked up to 2 days ahead and refrigerated. Rewarm before assembling the sandwiches.