Cut each slice of bacon in half crosswise so you have 24 shorter pieces. Take one filled jalapeno half and wrap it snugly with a piece of bacon, starting at one end and spiraling it around so most of the cream cheese is covered. Place the wrapped jalapeno, cut side up, directly into the cast iron skillet. Repeat with the remaining jalapeno halves, nestling them close together in a single layer.
Once all the jalapenos are wrapped and arranged in the skillet, transfer the skillet to the preheated oven. Bake for 20–25 minutes, or until the bacon is browned and starting to crisp and the jalapenos look softened and slightly blistered.
If you like your bacon extra crisp, turn the oven to broil for the last 2–3 minutes, keeping a close eye so nothing burns. The cream cheese should be hot and bubbling, the peppers dark green and roasted, and the bacon a deep, sizzling brown.
Carefully remove the cast iron skillet from the oven and let the jalapenos rest for about 5 minutes before serving; the cream cheese will be extremely hot. Serve them straight from the skillet while they’re still warm and melty, and don’t be surprised if they start disappearing before you can call everyone to the table.
If you’d like a little sweetness with the heat, lightly sprinkle brown sugar over the tops of the bacon-wrapped jalapenos before baking; it will melt into a sticky, caramelized glaze. For milder heat, choose larger jalapenos and scrape out every bit of the seeds and white membrane, or briefly soak the cleaned halves in cold water and pat dry before stuffing. You can also partially precook the bacon in a skillet for a few minutes to render some fat, then wrap the peppers so the bacon crisps faster without overcooking the jalapenos. To stretch the recipe for a crowd, cut the jalapenos into smaller boats by using smaller peppers or slicing the larger ones thinner, and use a little less cream cheese in each. If you don’t have a cast iron skillet, use a sturdy metal baking pan, but line it with foil for easier cleanup. Leftovers reheat well in a hot oven or toaster oven for a few minutes, though in most homes—especially with brothers hovering nearby—there won’t be many left to worry about.
