I don't know about you, but I can never resist the smell of bread pudding baking in the oven. It's one of those things that can drive you a little mad — and make you want to dig in before it's cooled down enough to eat.
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Note: The bread puddings can be made up to 2 days ahead. To serve, reheat in the oven at 350 degrees for 5-8 minutes. They will lose their flavor if refrigerated for a longer time. Serve warm.
Place the apple cider and sugar in a medium-sized, heavy-bottomed saucepan and bring to a boil over high heat. Reduce the heat to medium-high to medium and simmer vigorously, uncovered, until the liquid has almost completely evaporated and the syrup looks foamy, about 20-25 minutes.
Within a few seconds, the foam will become 2 shades darker (be careful not to burn the syrup at this stage). Immediately add the calvados and continue simmering for 1 minute. Remove from the heat and cool to room temperature.
Preheat the oven to 350 degrees.
Place the apple pieces in a large bowl and toss with the lemon juice. Add the cranberries, sugar, orange zest, and calvados and toss well. Add the brioche or challah cubes, toss again, and set aside. Butter and flour eight ½-cup ramekins or 1 medium-sized baking dish. Set aside.
In a medium-sized bowl, whisk together all of the ingredients until well blended. Pour the custard into the apple mixture and toss. Let stand for 5 minutes so that the bread soaks up some of the liquids. Spoon the mixture into the prepared ramekins up to ¼ inch from the rims. Bake until golden-brown and bubbly, about for 55-60 minutes.
When the bread puddings are warm, but not hot, unmold them. Then place each pudding in the center of a dessert plate, top side up. Top each pudding with a small scoop of ice cream, drizzle with the reduction and serve. Alternatively, if the bread pudding was made in a single baking dish, spoon the pudding in dessert bowls, scoop gelato or ice cream on the side, drizzle with the reduction, and serve.