1/2 cup (1 stick) unsalted butter, softened and divided
3 1/2 cup whole milk
1 1/2 cup heavy cream
1 tablespoons pure vanilla extract
6 large eggs
1 cup granulated sugar
scant 1 teaspoon ground cinnamon
1/4 teaspoon salt
For the Chocolate Sauce
1/4 cup unsweetened cocoa powder
1/4 cup granulated sugar
1/3 cup whole milk
2 tablespoons unsalted butter
1/4 cup bittersweet or milk chocolate pieces, whatever you have on hand that’s not unsweetened
Place a rack in the upper third of the oven and preheat oven to 375 degrees F. Place bread slices in a single layer on a rimmed baking sheet and toast until golden brown, about 5 to 6 minutes, but keep an eye on the bread to make sure it doesn’t burn.
Remove from the oven and allow to cool slightly.
Butter each slice of bread with the stick of butter, reserving 2 tablespoons of butter to grease a 9×13-inch pan.
Tear the buttered bread slices into large, bite-size pieces and place in the buttered dish. This may prove to be a rather messy endeavor, but that’s ok… sure is worth the messy fingers.
Add the dried cherries, if using, and move the bread around a bit to ensure the cherries are dispersed throughout.
In a medium bowl, whisk together milk, cream, vanilla, eggs, sugar, cinnamon, and salt. Whisk until well combined and smooth.
Pour the creamy egg mixture over the buttered bread in the pan. Press the bread down just slightly to ensure that it’s all well coated and the majority of it is soaking. Wrap lightly in plastic wrap and place in the refrigerator for 1 hour (or even overnight).
Just before baking, place a rack in the center of the oven and preheat oven to 350 degrees F. Unwrap bread pudding and place in the oven to bake until toasted, puffed and golden brown, about 40 minutes.
Remove from the oven and allow to cool for at least 30 minutes before serving.
Make the chocolate sauce while the bread pudding is baking. In a small saucepan over medium-low heat, whisk together cocoa powder, sugar, and milk. Once warmed and just beginning to bubble around the edges, add butter and chocolate pieces. Stir until completely melted and glossy. Remove from heat and allow to cool slightly before serving.
If you need to thin the sauce again before baking, just reheat over low heat lightly and add a splash more milk.
To serve, generously scoop bread pudding into bowls and drizzle lightly with warm chocolate sauce. Store remaining bread pudding covered in the refrigerator.