Preheat the oven to 400 degrees F. Line a baking sheet with foil and place a wire rack on top.
Rinse asparagus spears in cold water and pat them dry. Trim and discard the woody ends.
Lay out the spears on a tray or cutting board, drizzle with olive oil and sprinkle with salt and pepper. Toss to coat evenly.
Cut bacon slices in half lengthwise to make long, narrow strips, then wrap a strip of bacon tightly around one stalk of asparagus from top to bottom, slightly overlapping and leaving the very tops exposed.
Arrange the bacon wrapped asparagus onto the rack seam side down and not touching.
Bake in the preheated oven for 10 minutes, then flip them with tongs and bake for another 10 minutes. Flip them again and this time broil for 2-3 minutes or until the tops are really nice and crispy.
Notes
Feel free to assemble the bacon and asparagus ahead of time, then cover and refrigerate it. It should last for up to 3 days in the fridge.Any leftovers will keep in the fridge for up to 3 days. To reheat, use a toaster oven, oven, air-fryer, or pan on the stovetop. You can also zap it in the microwave if you prefer, but loosely cover the plate with a paper towel to protect the interior from bacon fat spatter.