1-First, preheat your oven to 325°F and lightly grease a 9-by-13-inch baking pan. Prepare the brownie batter by mixing 1 box (20 oz) dark chocolate brownie mix with 1 large egg, 1/2 cup canola oil, and 1/4 cup water as per the package directions. Spread it evenly in the pan and bake for 18 to 22 minutes, or until a toothpick comes out clean. Let the brownies cool completely before moving on.

2-Next, make the chocolate pudding by following the package directions with 3 cups whole milk, then chill it for at least 30 minutes. In another bowl, beat 1 package (8 oz) softened cream cheese and 1/4 cup granulated sugar until smooth and fluffy, about 3 to 4 minutes. Gradually add 2 cups heavy cream and 2 teaspoons vanilla extract, beating until well combined and whipped, which takes another 1 to 2 minutes.

3-Now, fold about 1 cup of the whipped cream mixture into the pudding to lighten it. Cut the cooled brownies into about 20 pieces and crush 1 package (14.3 oz) chocolate sandwich cookies coarsely in a zip-top bag using a rolling pin. In a 4-quart trifle dish, layer half of the brownies, then half of the pudding, half of the crushed cookies, and half of the remaining whipped cream mixture. Repeat the layers and garnish with chocolate shavings.