Preheat broiler to 500°F degrees. Arrange the oven rack in the center of the oven, not directly under the broiler. Prepare a baking sheet with a spritz of nonstick cooking spray and set a wire baking rack on it.
Wearing gloves, slice the jalapeños in half lengthwise and remove the seeds and membranes.
Scoop 1 tablespoon of pimento cheese into each pepper half.
Wrap 1 slice of bacon around each stuffed jalapeño, securing the bacon with a toothpick, if needed. Arrange the stuffed and wrapped peppers on the prepared baking rack.
Broil the poppers for about 5-7 minutes, flip them over, and broil another 3-5 minutes—watching carefully to avoid burning—until the bacon is browned and chewy-crisp, the peppers have softened, and the cheese is bubbly.
Remove from oven and let the poppers cool for 2-3 minutes. Remove toothpicks before serving.