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Remove top rack and place bottom rack on lowest level of oven; preheat oven to 350°F.
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Carefully cut the top from the pineapple without spoiling the frond, and remove the pulp from inside the top, reserving the pulp in a bowl.
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With a grapefruit knife, remove the core and the pulp from the rest of the pineapple, taking care to leave 1/4 inch layer on the inside of the rind to keep juices from running out while baking.
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Place the frond in water to cover, to soak in preparation for baking.
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Slice the banana thinly, dice the pineapple pulp; combine in a bowl with the 1/4 cup sugar.
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Pour the rum into a heatproof bowl or saucepan.
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Ignite the rum and when flame subsides, pour over the fruit mixture and stir gently.
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Place the empty pineapple bottom upright into a baking dish.
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Fill the pineapple bottom with the fruit.
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Remove the frond from the water and cover it with aluminum foil.
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Secure the top of the pineapple to the bottom with toothpicks.
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Bake the pineapple, standing upright, for 25 minutes.
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Remove the foil from the fronds and serve hot.