Set your oven to 375F.
Cut the pound of bacon in half. Put the brown sugar in a shallow bowl. Take a half a slice of bacon and dredge it through the brown sugar. Put a chunk of pineapple on one end of the bacon slice and roll up. Secure with a toothpick.
I put a cookie cooling rack into a foil-lined jelly roll pan. Lay the bacon pineapple bundles onto the rack.
Bake for at least 25 minutes, or until the bacon looks brown and crispy. Sometimes I pop them under the broiler for the last few minutes just to get them really crisp. But watch out – the sugar will burn!