Step 1: Prepare Your Ingredients
Remove the cream cheese from the refrigerator and let it sit at room temperature for 30 minutes to soften—this ensures smooth mixing without lumps. Meanwhile, grate your cheddar cheese using the large holes of a box grater or the shredding disc of your food processor. Freshly grated cheese is crucial for the best texture and flavor. Open your jar of pimentos and drain them thoroughly in a small strainer, pressing gently with a spoon to remove excess liquid. If the pimento pieces are large, chop them into smaller, uniform pieces (about ¼-inch dice).

Step 2: Combine the Creamy Base
In a large mixing bowl, combine the softened cream cheese and mayonnaise. Using a rubber spatula or sturdy spoon, mix these together until smooth and well blended with no lumps of cream cheese remaining. This creates your creamy base that will hold all the other ingredients together. If your cream cheese isn’t quite soft enough and you’re getting lumps, you can use a hand mixer on low speed for 30 seconds to smooth it out.

Step 3: Add Seasonings
To the cream cheese and mayonnaise mixture, add the Worcestershire sauce, garlic powder, onion powder, cayenne pepper, and black pepper. Stir until all the seasonings are evenly distributed throughout the creamy base. This is when your pimento cheese starts to smell amazing!

Step 4: Fold in the Cheese
Add the freshly grated sharp cheddar cheese to the bowl. Using your rubber spatula, gently fold the cheese into the creamy mixture. Take your time here—you want to coat every shred of cheese with the mayonnaise mixture while maintaining some of that chunky texture that makes homemade pimento cheese so special. Mix until everything is well combined and evenly distributed, but don’t over-mix or the cheese will start to break down too much.

Step 5: Add the Pimentos
Add the well-drained, diced pimentos to the bowl. Gently fold them in, distributing them evenly throughout the mixture. You want those beautiful red pieces visible throughout your pimento cheese for both flavor and visual appeal. Make sure they’re evenly incorporated so every bite has that sweet pimento flavor.

Step 6: Taste and Adjust
This is the most important step! Taste your pimento cheese and adjust the seasonings as needed. Does it need more tang? Add another small splash of Worcestershire or a squeeze of lemon juice. Want more heat? Add a pinch more cayenne or a dash of hot sauce. If the cheese you used was particularly salty, you probably won’t need any additional salt, but if it tastes flat, a tiny pinch can help. Remember, the flavors will develop and intensify as it sits, so don’t over-season.

Step 7: Chill and Serve
Transfer your pimento cheese to an airtight container and refrigerate for at least 2 hours before serving. This chilling time allows the flavors to meld together beautifully and the texture to firm up slightly, making it easier to spread. For the very best flavor, make it a day ahead if possible. Before serving, let it sit at room temperature for 15-20 minutes to soften slightly—cold pimento cheese is harder to spread and the flavors are muted.

Step 8: Presentation
When ready to serve, transfer your pimento cheese to a pretty serving bowl. For an attractive presentation, you can smooth the top and create a small well in the center, then drizzle with a little extra olive oil or sprinkle with paprika or fresh herbs. Serve with crackers, bread, vegetables, or however you prefer!