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Combine the first 3 ingredients in a small saucepan; cook over medium heat 4 minutes or until mixture is thick. Add bourbon; cook until mixture is reduced to 1/4 cup (about 5 minutes). Remove from heat. Add sliced bananas and toss gently. Spoon banana mixture into a bowl; set aside.
Combine milk and next 5 ingredients (through eggs) in a large bowl, stirring well with a whisk. Add bread mixture evenly among 6 (8-oz) ramekins coated with cooking spray. Divide banana mixture evenly over bread mixture. Place ramekins on a small baking sheet. Cover and chill 30 minutes.
Preheat oven to 375 F.
Uncover and bake at 375 F for 25 minutes or until set. Drizzle caramel topping evenly over bread puddings.
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