1 (1 pound) loaf day-old Italian bread
5 large eggs
1 1/2 cups sugar
4 cups half and half
1 tablespoon vanilla extract
24 chocolate sandwich cookies, quartered
1/2 cup heavy whipping cream
1 (14 ounce) can sweetened condensed milk
12 chocolate sandwich cookies, crushed
FOR BREAD PUDDING:
- Preheat oven to 350°F. Spray 9×13-inch baking pan with nonstick cooking spray. Set aside.
- Cut bread into one-inch cubes and place in large mixing bowl. Set aside.
- Combine eggs, sugar, half and half, and vanilla extract in a medium mixing bowl. Whisk until fluffy. Pour over cubed bread, stirring gently to mix. Set aside for 15 minutes and allow egg mixture to soak into bread.
- Gently stir in chocolate sandwich cookies.
- Pour bread pudding mixture into prepared baking pan and spread out evenly.
- Bake for 45-50 minutes, until top has set and a thermometer placed in the center reads 165°F.
- Cool for 15 minutes.
- Whip heavy whipping cream in bowl of an electric mixer fitted with whisk attachment until medium peaks form.
- Cut bread pudding using Mickey Mouse-shaped cookie cutter and place on a plate. Drizzle with 1-2 teaspoons of sweetened condensed milk.
- Top each serving with 2 tablespoons whipped cream and 1 tablespoon of crushed chocolate sandwich cookies.