Sloppy Joe Grilled Cheese



  • 1 tbsp extra-virgin olive oil
  • 1 medium onion, chopped
  • 1 lb. ground beef
  • 2 cloves garlic, minced
  • ½ c. ketchup
  • 1/3 c. packed brown sugar
  • 2 tbsp yellow mustard
  • 1 tbsp chili powder
  • Kosher salt
  • Freshly ground black pepper
  • 4 tbsp butter, for bread
  • 8 slices sandwich bread
  • 2 cups shredded cheddar


  • In a large skillet over medium heat, heart oil. Add onion and cook, stirring, until soft, about 5 minutes. Add ground beef and cook, stirring and breaking up meat, until no longer pink, 6 to 8 minutes. Drain fat.
  • Return beef mixture to skillet over medium heat and stir in ketchup, garlic, brown sugar, mustard, and chili powder and season with salt and pepper. Simmer until thick, 5 minutes. Transfer mixture to a plate and wipe skillet clean.
  • Assemble sandwiches: butter one side of each bread slice. Place 1 slice butter-side down in skillet and spoon over sloppy joe mixture. Top with cup of cheddar cheese and one more slice bread, buttered-side up.
  • Cook over medium heat until bread is golden and cheese is melty, about 3 minutes per side. Repeat with remaining ingredients to make 4 sandwiches total.