1poundshrimp(16/20), deveined, shell removed, tail on
1/3cupdark brown sugar, lightly-packed
freshly-cracked black pepper
snipped chives, for garnish
Soak 16-20 toothpicks in water for 30 minutes. Preheat oven to 400 degrees F.
Line a rimmed baking sheet with foil and arrange bacon slices in a single layer. Bake 6-8 minutes, until fat is beginning to render but bacon is not yet crisp. Remove from oven, drain bacon on paper towels, and cut each slice in half. Carefully discard any remaining bacon fat on the pan.
Lightly season shrimp with salt and pepper. Wrap one piece of bacon around each shrimp, overlapping ends and securing with a soaked toothpick.
Place a wire cooling rack on the baking sheet and arrange wrapped shrimp in a single layer. In a small bowl, stir together brown sugar and bourbon until dissolved. Brush glaze onto the front and back of each bacon-wrapped shrimp.
Bake shrimp for 5 minutes. Remove from oven, brush with a second layer of glaze, and season with freshly-cracked black pepper. Continue baking 5-8 minutes, until shrimp are pink and opaque, and bacon is crisp.