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1
The day before you want to serve this dessert, if possible, put raisins in a small saucepan, cover with water, and bring to a boil.
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2
Remove from heat and drain.
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3
Place plumped raisins in a plastic container with a tight-fitting cover and sprinkle with the rum.
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4
Cover and let macerate overnight.
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5
Preheat oven to 325 degrees.
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6
Melt the butter and cool slightly.
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7
Cut the challah in half, and cut one of the halves into thin slices.
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8
Cut remaining bread into cubes.
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9
Put diced challah in the bottom of the baking dish.
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10
Strew with the raisins and rum and half the butter.
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11
Dip one side of each slice of challah into the butter and arrange, slightly overlapping and buttered side up, over the top of diced challah and raisins.
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12
Combine the milk, cream and sugar, and vanilla bean in a saucepan.
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13
Bring to a boil over medium heat.
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14
Remove from heat, add chocolate, and allow to stand 3 minutes; whisk smooth.
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15
Whisk eggs until combined in a large mixing bowl, then strain the milk mixture into the eggs and beat them together.
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16
Do not overbeat or the custard will have a great deal of foam on the surface.
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17
Strain the custard back into the pan and use a large spoon to skim any foam from the surface.
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18
Pour the custard over the challah.
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19
Place the baking dish in another larger pan and pour warm water into it to come halfway up the side of the baking dish.
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20
Bake the bread pudding for about 45 minutes, until the custard is set and the challah is an even color.
