Start by baking your chocolate cake or brownies according to the package or your favorite homemade recipe. Once baked, let the cake cool completely in the pan for about 30 minutes, then transfer it to a wire rack.

Prepare the chocolate pudding according to the package instructions or your homemade recipe. Whisk the pudding mix with milk in a medium bowl until it thickens, about 2-5 minutes. Set aside to cool.

In a large mixing bowl, combine cold heavy whipping cream with powdered sugar and vanilla extract. Whip the cream on medium-high speed until soft peaks form, about 4-6 minutes.

Layer chunks of chocolate cake at the bottom of a trifle bowl, followed by cherry pie filling, a layer of chocolate pudding, and a dollop of whipped cream. Repeat layers until all ingredients are used, ending with whipped cream.

Cover the trifle with plastic wrap and refrigerate for at least 1-4 hours or overnight. When ready to serve, garnish with fresh cherries, shaved chocolate, and icing sugar or cocoa powder.