Tightly wrap one piece of bacon around one little smokie. Place seam down in a glass 13x9 dish. Repeat with remaining little smokies.
Sprinkle evenly with brown sugar. There should be a thin layer over all the little smokies. Cover and refrigerate for at least 1 hour.
Preheat oven to 350°F. Uncover little smokies and bake for 40-50 minutes. Bacon should be crispy and sugar deeply caramelized.
Start with cutting the bacon into thirds. If you leave the strips any longer they will never crisp up. There may be a few pieces of bacon left over.
You can make this ahead and bake when you are ready!
As for the pan you use, this makes a big difference. I asked my mom how she did it and she said she uses a glass baking dish, not a foil-lined baking sheet. To clean up after, she fills the pan with hot tap water and lets it sit for a few minutes. The caramelized sugar dissolves away.
Letting them marinate makes all the difference in flavor.