Preheat oven to 375 degrees and line baking sheet with parchment paper.Place bacon slices on paper towel-lined plate and microwave for 3 minutes.
Set aside to slightly cool.In a medium bowl, add cream cheese, shredded sharp cheddar, salt, and pepper and microwave for 15 seconds.
Stir together.Carefully scoop cream cheese mixture into plastic baggie.
With a scissors, snip off corner of baggie and pipe contents into jalapenos.Wrap bacon slices around jalapenos and pin with toothpick.Place jalapenos on prepared baking sheet and bake for 15 minutes.Increase oven heat to broil and broil for 2-3 minutes, watching to ensure cream cheese does not burn.Remove from oven and allow to cool slightly before eating.