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Put the 2 cups of milk, yolks, flour, and salt in a blender. Blend until smooth. Pour into a 3-quart saucepan (non-stick recommended).
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Add remaining 2 cups milk, sugar, vanilla bean, and chocolate.
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Slowly bring to a boil over medium heat, stirring constantly. Let boil for 30 seconds.
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Pour the mixture through a strainer into a large bowl. It will be very thick so you may need to press it through.
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Scrap the seeds from the vanilla bean and discard bean shell. Add the seeds, cream, and brandy to the bowl.
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Whisk to combine. Place plastic wrap directly on top of the pudding.
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Cool to room temperature then chill thoroughly (best overnight). Spread 3 1/2 cups of pudding over cream cheese layer. Enjoy the remaining separately.
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If not serving immediately, lay plastic wrap directly on top of pudding to prevent a skin from forming.