Quickly warm pineapple in butter and brown sugar, then spoon the softened fruit over crumbled pound cake and dulce de leche ice cream.
In a small heavy skillet, melt butter over medium heat. Stir in brown sugar, honey and cinnamon. Bring to boiling; reduce heat. Simmer, uncovered, for 2 minutes. Add pineapple. Cook and stir for 1 to 2 minutes more or until heated through. Remove from heat.
Scoop ice cream into four dishes. Top with crumbled cake, warm pineapple mixture, whipped cream and a cherry. Serve immediately.
To toast pound cake: Preheat oven to 350°. Spread crumbled pound cake pieces on a 15x10x1-inch baking pan. Bake for 5 to 10 minutes or until lightly toasted.