Split the jalapenos lengthwise from the stem to tip, then cut crosswise making a shallow "T" at the top (the stem end). Fold the peppers open and remove the veins and seeds with a paring knife.
Put the pimento cheese into a pastry bag or a heavy-duty plastic bag with a corner snipped off. Fill each jalapeno with 1 to 1 1/2 tablespoons pimento cheese, and press closed. In a shallow bowl, mix the breadcrumbs with the Italian seasoning. Dip the poppers first in the eggs and then in the breadcrumb mixture. Repeat, dipping first in egg and again breadcrumbs, for double dredge. Set the breaded poppers on a drying rack.
Fill a large cast-iron skillet with 1 inch of oil; heat over medium heat until the oil reaches 325 degrees F. In two batches, add the poppers and cook until golden brown, flipping halfway through, 5 to 6 minutes total. Drain on a wire rack set over a baking sheet and season with salt.
Serve immediately, but be careful not to burn your tongue!
Mix the cream cheese in a bowl until smooth, about 1 minute. Mix in the Cheddar, garlic powder and roasted red peppers. Add salt and pepper to taste, but do go heavy on the salt; start with 1/4 teaspoon and go from there--this is where all seasoning is coming from for the whole dish!!
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