Preheat oven to 425˚F. Place an oven safe rack inside a parchment lined baking sheet (for easy cleanup).
Place trimmed asparagus in a large bowl or on a second baking sheet. Drizzle with olive oil and season with salt and pepper; toss to coat evenly.
Divide asparagus spears into 6 bunches of 4 to 5 spears. Starting about an inch below the tips, wrap each bundle with 1 slice of bacon, pressing or tucking under ends to secure and taking care to minimize areas where bacon overlaps. Arrange bacon wrapped asparagus bundles in a single layer on oven safe rack, leaving some space between each.
Bake in preheated oven 18-22 minutes, until asparagus is tender and bacon is cooked to your liking. Serve.
Notes
If you like your bacon really crispy, precook it as I do for my Bacon Wrapped Shrimp or be sure to use thinly sliced bacon.