How could caramel, pineapple, ice cream and pound cake be bad? You can also use an indoor grill or grill pan for this recipe.
Melt butter in a small saucepan over high heat, add the brown sugar and rum and cook, whisking until the sugar has melted and the mixture is smooth. Whisk in heavy cream and cook until heated through and slightly thickened. Transfer to a bowl and keep warm.
Heat grill to high. Brush pineapple on both sides with oil and place on grill. Grill until golden brown and caramelized on both sides, about 6 minutes. Remove from the grill, stack the slices and cut into chunks. While the pineapple is grilling, place the pound cake on the grill until lightly golden brown on both sides, about 20 seconds each. Remove the pineapple from the grill & either slice or cut into chunks.
Top each piece of pound cake with some of the pineapple & drizzle with caramel-rum sauce. Top with more pound cake, ice cream and cherries, if desired.