"This is one of my favorite pork dishes; my dad taught me to make it for the first dinner I cooked when I was 11. I like to serve this with some kind of sweet potato or garlic mashed potatoes and a vegetable."
Heat 1 teaspoon oil in a skillet over medium heat; add bacon and stir until starting to soften and still underdone, about 3 minutes. Mix apples and brown sugar together in a bowl. Add to skillet; cook and stir filling until glazed, about 2 minutes.
Heat 1 teaspoon oil in a skillet over high heat; fry pork chops, about 45 seconds per side.
Transfer each pork chop to a flat work surface; lay flat. Use the tip of a sharp boning or paring knife to create a pocket by making a slit in the side; repeat with remaining pork chops.
Stuff pork chops with filling and secure closed with toothpicks. Pour apple juice into a 9x13-inch baking pan; add pork chops. Sprinkle Cheddar and Monterey Jack cheese on top.
Bake in the preheated oven until pork chops are no longer pink in the center, about 45 minutes. An instant-read thermometer inserted into the center should read 145 degrees F (63 degrees C).