Ingredients
10ozsemisweet chocolate
4cupshalf and half
1¼cupsdark brown sugar
⅓cupnatural unsweetened cocoa powder
⅓cupbourbon
1tspcinnamon
8large eggs
¼tspsalt
2tspvanilla extract
1large challah,about 1⅓ lb, cut into 1-inch cubes
confectioners’ sugar,optional
vanilla ice cream,optional
Preparation
Chop the chocolate into ¼-inch chunks. Reserve ⅔ cup and set aside.
In a medium saucepan, whisk together the half and half, brown sugar and cocoa powder; bring to a boil. Off the heat, whisk in the remaining chocolate, bourbon and cinnamon.
In a large bowl, whisk together the eggs, salt and vanilla extract. Very gradually, pour the hot chocolate mixture into the egg mixture, whisking vigorously to combine (pour slowly, especially at the beginning, or the hot chocolate mixture will scramble the eggs).
Add the bread cubes to the custard; cover and let soak in the fridge for at least 1.5 hours or overnight.
Preheat the oven to 325 degrees F. Grease a 9x13x2-inch glass baking dish with butter or nonstick cooking spray.
Transfer the chocolate-soaked bread to the prepared baking dish, and spread the bread around evenly. Scatter the reserved ⅔ cup of chocolate over top, then use a spoon to push about half of the chocolate bits down into the pudding.
Bake for 45 to 50 minutes until slightly puffed and set in the center. Let cool about 10 minutes, then serve warm, dusted with confectioners’ sugar and topped with vanilla ice cream.
