Steps:
- Brush 8x8x2 inch glass baking dish with 1 tablespoon melted butter. Simmer half and half and brandy in heavy large saucepan 3 minutes. Remove from heat. Add 1 cup chocolate chips. Let stand 1 minute, then whisk until chocolate is melted and mixture is smooth. Whisk in brown sugar and 1/2 teaspoon cinnamon. Let stand until cool, about 20 minutes. Whisk in eggs, then vanilla and salt. Stir in bread. Let stand 30 minutes. Spread half of pudding mixture (about 2 1/2 cups) in prepared dish. Sprinkle with 2 cups chocolate chips. Cover with remaining pudding mixture. (Can be made 1 day ahead. Cover; chill.) Preheat oven to 350 degrees F. Bake pudding uncovered until puffed and firm in center, about 45 minutes. Remove from oven; let cool 10 minutes. Beat chilled cream, sugar, and 1/2 teaspoon cinnamon in medium bowl until peaks form. Spoon pudding into bowls. Top with whipped cream.
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