Preheat broiler with rack in upper third of oven.
Trim top of pineapple and carve into 8 wedges lengthwise. Trim away the core and carve the pineapple away from skin then into 1/2-inch slices. Leave the slices in the shell or boat of the skin and arrange the wedges on baking sheet.
Sprinkle an even layer of dark brown sugar the length of each wedge of pineapple. Broil until deeply brown and bubbly, serve warm.