Golden pineapple rings and glossy maraschino cherries form a sticky, caramelized crown over a tender vanilla cake, and it's every bit as show-stopping as the classic diner version. The brown sugar mixture bubbles up into that irresistible amber glaze, while a batter built on flour, baking powder, and a good hit of reserved pineapple juice keeps the crumb soft and moist all the way through. Beating the sugar until pale and fluffy before adding the eggs is what gives this cake its light, tender texture, and alternating the dry ingredients with pineapple juice keeps everything perfectly balanced. That dramatic flip from pan to plate is still the best part, revealing a burnished fruit pattern that looks like it took way more effort than it actually did. Serve it warm with the caramel still glistening, and you've got a nostalgic dessert that fits neatly into a dairy free spread without missing a beat.
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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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