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This meatloaf is hiding a few cheesy secrets: Cheez-It crackers (instead of breadcrumbs) in the meatloaf mixture adds the exclamation point to pimiento cheese both in and baked atop the loaf.
Gather all ingredients.
Preheat oven to 350°F. Coat an 8 1/2- x 4 1/2-inch loaf pan with cooking spray; line a large rimmed baking sheet using aluminum foil.
Whisk together onion, milk, garlic, eggs, 2 tablespoons of the ketchup, and 2 tablespoons of the Worcestershire sauce in a large bowl until evenly combined. Stir in crushed cheese crackers until combined; set aside, and let crackers hydrate for 5 minutes.
Add ground beef, paprika, salt, pepper, 1 cup of the cheese, 2/3 cup of the pimientos, and 1/8 teaspoon of the cayenne to cracker mixture in large bowl; gently stir together until combined. Firmly press beef mixture into prepared loaf pan; invert pan onto prepared baking sheet to release meatloaf. (Alternatively, shape meat mixture into a 8- x 4-inch loaf shape on baking sheet by hand.) Brush top and sides evenly with remaining 2 tablespoons ketchup.
Bake in preheated oven until a thermometer inserted into center of meatloaf registers 155°F, 45 to 50 minutes.
While meatloaf is baking, stir together granulated garlic, onion powder, and remaining 1/2 cup cheese, 1 tablespoon diced pimientos, 1/4 teaspoon Worcestershire, and 1/8 teaspoon cayenne in a medium bowl until well combined.
Remove meatloaf from oven, and sprinkle reserved cheese mixture evenly over top of meatloaf. Return to oven, and bake at 350°F until cheese is melted and a thermometer inserted into center of meatloaf registers 160°F, about 8 minutes. Let cool slightly, about 10 minutes, before slicing and serving.