Preheat the oven to 350 degrees F. Grease a 6-cup (9 1/4 by 5 1/4 by 2 2/4-inch) loaf pan with butter.
In a large saucepan, over medium heat, add the half and half. When the cream comes up to a gentle boil, whisk in 1 cup of the chocolate chips, whisking constantly until the all of chips have melted and are incorporated into the cream, remove from the heat. Whisk the eggs, sugar, cinnamon, nutmeg, vanilla and Grand Marnier together in a large mixing bowl until very smooth. Add the egg mixture to the cream mixture and mix well. Add the bread, incorporate thoroughly and let the mixture sit for 30 minutes, stirring occasionally. Pour half of the mixture into the prepared pan. Sprinkle the top with the remaining chocolate chips. Pour the remaining bread mixture over the chocolate chips. Bake until the pudding is set in the center, about 55 minutes. Let cool for 5 minutes. To serve, cut the pudding into 1-inch thick slices. Top with the spiced cream.
Beat the cream with an electric mixer on high speed in a large mixing bowl for about 2 minutes. Add the sugar, cinnamon, and nutmeg and beat again until the mixture thickens and forms stiff peaks, another 1 to 2 minutes.
Yield: 4 cups