Place a wire rack on a jelly roll pan. This will allow the grease to drain off the bacon and the bacon to crisp up.*
Cut 1 - 3 inches (as needed) off of the woody end of the asparagus creating even length spears.
Divide asparagus into bundles of 3 to 5 spears depending on thickness and amount of bacon you want to use.
Then wrap each bundle tightly with bacon. Lay the bundles on the wire rack in the jelly roll pan, tucking the bacon end under so it doens't unwrap.
Season with garlic and pepper.
Roast in a preheated oven for 30 minutes at 400* or until the bacon is crisp. Flip part way through roasting to crisp up the bottom side.*