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.
Cookies n’ Cream Bread Pudding at Pacific Wharf Cafe