Golden pineapple rings and glossy maraschino cherries sit in a buttery brown sugar caramel that bubbles up around the edges as this cake bakes, then flips into that signature glistening top everyone fights over. The cake layer bakes up rich and tender, with vanilla and reserved pineapple juice keeping the crumb moist and giving it real depth of flavor. Creaming the butter and sugar until pale and fluffy, then folding in eggs one at a time, builds the kind of structure that holds its shape beautifully once inverted onto the plate. That confident flip at the end reveals a deep amber caramel layer studded with fruit, and a few minutes of resting time is all it takes before it's ready to slice. It's a showstopper dessert that works great for a gluten free table, with all the nostalgic flavor of the classic version intact.
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Preheat the oven to 350°F (175°C). If using a 10-inch oven-safe skillet, place it over medium heat on the stovetop. If using a 9-inch round cake pan, use a small saucepan for this step and transfer the topping to the pan afterward.
Melt the 4 tbsp butter in the skillet (or saucepan) over medium heat, then add the brown sugar and stir until the sugar is fully moistened and the mixture is bubbling and smooth, about 2 minutes. Remove from heat. If using a cake pan, pour the brown sugar mixture evenly into the bottom of the pan.
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