1 cup raisins, or as many as desired
Grated zest of 1 orange
1 cup brandy
4 ½ cups half and half
9 large egg yolks, at room temperature
1 cup plus 2 tablespoons sugar
1 tablespoon vanilla extract
6 cups diced (1/2 inch) soft crustless challah, brioche, or white bread
6 ounces semisweet chocolate, coarsely chopped
Vanilla ice cream or whipped for serving, if desired
Put the raisins and orange zest in a small bowl, add the brandy, and let the raisins and zest soak, covered, in the refrigerator for 24 hours, or up to 1 week.
Put the ½ and ½ and half of the sugar in a small saucepan and bring to a simmer over low heat. Meanwhile, whisk the egg yolks, remaining sugar and vanilla in a large bowl. Whisk one third of the warm cream into the egg mixture, a little at a time, to prevent scrambling the eggs, then whisk in the rest of the cream mixture.
Pour the warm mixture over the bread. Stir in the raisins (as much as you’d like) and the chocolate. Cover the bowl with plastic wrap and refrigerate for at least 24 hours or up to 48 hours.
Put a rack in the center of the oven and preheat the oven to 325˚F. Pour the bread pudding into a heat proof bowl. Place the bowl in a roasting pan or large dish and fill the pan with enough warm water to come halfway up the sides of the bread pudding dish. Bake, uncovered, until the pudding is just set, about 60 minutes; when you shake the pan, the custard should wobble for just a moment.
Remove the pan from the oven and carefully remove the bread pudding dish. Serve the bread pudding hot, with a scoop of vanilla ice cream or whipped cream right on top.