Remove crusts from the sliced bread. You should have about 9, square (ish) pieces of bread. Cut into 4 triangles. In a glass bowl set over a saucepan with barely simmering water (make sure the bowl does not touch the water), place chocolate pieces, whipping cream, bourbon, sugar, butter and cinnamon.
Wait until the chocolate and butter have melted, stirring gently making sure sugar has dissolved. Remove the bowl from heat and give it a good stir to mix all of the ingredients.
In a small mixing bowl, whisk the eggs. Using a ladle, while whisking, pour the a small amount of eggs into the chocolate mixture to temper the eggs, so you do not cook them! Continue adding a little at a time until you have added an entire ladle of eggs. Whisk egg-chocolate mixture into the balance of the eggs until thoroughly blended.
Lightly butter casserole dish (butter is better than spray oil in this case as it will add to the richness of the pudding and keep it from sticking).
Ladle about ½ inch of the chocolate mixture into the dish, arranging one layer of the bread triangles over the chocolate, overlapping in rows. Pour half the remaining chocolate mixture over the first layer. Repeat with the rest of the bread triangles finishing off with the rest of the chocolate mixture.
Use a fork to gently press the bread into the liquid mixture making sure all pieces are soaked. Cover the dish with plastic wrap, allowing to sit at room temperature for 2 hours before transferring to the fridge for a minimum of 24 hours, ideally 48 hours, but due to life getting in the way, mine sat for 5 days in the fridge and turned out amazing.
Baking Chocolate Bread Pudding
Preheat oven to 350° F and move oven rack to higher side of oven (not all the way to the top). Remove plastic wrap from dish and bake for 30-35 minutes, checking at 25. Top should be crunch and the inside "soft and squidgy" a quote from the original recipe, love that description! Let stand for 10 minutes before serving. Serve with well chilled heavy cream or try it with this amazing Creme Anglaise!
How to Make Your Own Caster SugarYou can easily make your own caster sugar by simply placing a slightly greater amount of sugar that you will need in your recipe into a food processor. Process for about 1-2 minutes watching closely, if you go too long you will make powdered sugar. You may want to place a towel over the top of the processor as the dust sneaks its way out of the processor.