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1
Preheat the oven to 325F.
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2
Combine the milk, butter, sugar, eggs, and vanilla in a large mixing bowl.
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3
Whisk until incorporated and smooth, but dont over-whisk.
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4
Line a baking dish with two thirds of the challah slices, lining the edges too.
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5
Sprinkle with half the chocolate chips and half the raisins.
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6
Cover with the remaining challah slices, layering them one on top of the other.
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7
Top with the remaining chocolate chips and raisins, making sure the chips and raisins get inside the layers created by the challah slices.
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8
Pour the milk mixture over the top of everything.
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9
Wrap the baking dish tightly with aluminum foil.
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10
Bake 50 minutes, then remove the foil and cook 15 minutes longer, until set in the middle and lightly browned on top.
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11
While the pudding is baking, make the vanilla cream: Combine the half-and-half, vanilla, and sugar in a large saucepan.
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12
Heat over medium heat, whisking regularly, until steaming hot.
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13
Place the egg yolks in a large mixing bowl and gradually add the hot half-and-half mixture to the egg yolks, whisking vigorously all the while.
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14
When all the half and-half mixture has been whisked into the egg yolks, return the mixture to the saucepan and heat over medium heat, whisking constantly.
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15
Cook until the mixture thickens.
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16
Spoon over the pudding and serve.
