Pre-heat oven to 400 degrees. Wash the peppers, pat dry and slice in half lengthwise. Wash hands with hot, soapy water after handling peppers.
Use a small knife to remove the seeds and membrane. Leave some in if you like more heat.
Place 4 slices of bacon on folded paper towels. Microwave 1-2 minutes until the bacon begins to cook and release grease. Remove from microwave and set aside until cool.
Use a sharp knife to slice the bacon strips in half lengthwise.
Stuff each pepper half with cream cheese until full and slightly mounded. Lightly press cheddar cheese onto the top.
Lay the cheese-stuffed pepper in the center of a bacon slice and wrap the bacon around the pepper so that the ends are on the underside. You might have to stretch it a bit. (see photo) Sprinkle with salt and pepper to taste.
Place the bacon-wrapped poppers on an un-greased baking sheet. Bake in 400 degree oven until the poppers are golden brown and the bacon is fully cooked. (about 12-15 minutes)
Remove from oven and serve piping hot with a side of cold ranch dressing.