1. Preheat oven to 425 degrees F./220 degrees C. (or 400 degrees F./200 degrees C. if you have convection).
2. Remove the top and the bottom of the pineapple, and peel it. Cut the pineapple into quarters lengthwise and remove the core from each quarter. Cut each quarter in half widthwise so that you have 8 pieces. Season the pieces all over with granulated sugar.
3. In a heavy, ovenproof skillet, melt the butter over medium-high heat. When the butter is melted, put the pineapple pieces into the pan with one of the cut sides down. Put the pan in the oven and roast for 10 minutes. Tip the pineapple on their other cut sides and continue to cook until they’re nicely browned, another 5 minutes or so.
4. While the pineapple is roasting, put the brown sugar in a small, high-sided saucepan along with just enough water to make the sugar look like wet sand. Cook over high heat until the water cooks off and the sugar froths and bubbles, 2 to 3 minutes; then reduce the heat to medium-low and cook for another minute or so. Add the cream in a steady stream (be careful -- it will boil violently on contact with the melted brown sugar) and stir to incorporate.
5. Serve the roasted pineapple on the skin but sliced from it and cut into bite-sized pieces, as in the photos, topped with the ice cream and drizzled with the warm caramel sauce.
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Michael Ruhlman is an author, writer and food blogger. His books include Ruhlman's Twenty, Ratio: The Simple Codes Behind the Craft of Everyday Cooking, The Elements of Cooking: Translating the Chef's Craft for Every Kitchen and The Making of a Chef: Mastering Heat at the Culinary Institute of America, as well as several cookbook collaborations and non-fiction books.