Grilled Pineapple Upside-Down Cake

This grilled pineapple upside-down cake takes the familiar comfort of a supper-club classic and flips it into something smoky, bright, and undeniably summer-ready. Instead of stewing pineapple in a pan, we give each ring a quick ride over high heat so the fruit develops dark char marks and concentrated sweetness; that caramelized surface, combined with a buttery brown-sugar base in a hot cast-iron skillet, produces a glossy top that reads as both rustic and elegant. The cake layer is a simple vanilla batter that bakes through over indirect heat, creating a tender, fine crumb that soaks up the backnotes of char and rum-like brown sugar without getting soggy.

This version works because it balances contrast: the caramel delivers deep sweetness and chew, the char adds smoke and complexity, and the cake keeps things light and tender. It’s a crowd-pleaser for backyard barbecues or any time you want a dessert that arrives looking dramatic but doesn’t require pastry-level skills. Little choices matter—reserving pineapple juices, warming the skillet before you pour batter, and giving the caramel a few minutes to set—so the final unmolding reveals glossy rings that practically glisten on the platter.