To start, you’ll want to prepare the pimento cheese. In a medium bowl, combine the shredded sharp Cheddar cheese, shredded Monterey Jack cheese, mayonnaise, cream cheese, diced pimientos, and cayenne pepper. Using a wooden spoon, mix everything together until well blended. You’ll want a creamy, cohesive texture. If you like, you can adjust the amount of diced pimientos according to your taste. Refrigerate the mixture until you’re ready to use it.
Next, it’s time to work on the beef patties. In a large bowl, gently mix the ground chuck with Worcestershire sauce, kosher salt, and black pepper. Be careful not to overwork the meat, as this can make the burgers tough. Shape the mixture into four to five patties, depending on how large you want them. Make a small depression in the center of each patty to help them cook evenly.
Preheat your grill or grill pan over medium-high heat. Once hot, place the patties on the grill, making sure to leave some space in between them. Grill the burgers for about four to six minutes on each side, or until they reach your desired level of doneness. To add a special touch, about a minute or two before they finish cooking, top each burger with approximately a quarter cup of the pimento cheese mixture, allowing it to melt beautifully.
Finally, it’s time to assemble your burgers! Take a leaf of red leaf lettuce and place it on the bottom of each toasted burger bun. Carefully place the grilled patty on top and finish with the top bun. You can also add any extra toppings you enjoy, like pickles or tomatoes, if desired.