Preheat the oven to 350℉ and prepare a springform pan with butter or cooking spray.
In a large bowl, combine the cake mix, cherry pie filling, and eggs. Stir gently with a wooden spoon until fully mixed, keeping the cherries mostly intact.
Pour the batter into the prepared pan and bake for 40–50 minutes, or until a toothpick inserted in the center comes out clean.
While hot, gently press down the dome in the center of the cake to level it, then let the cake cool.
In a small saucepan, combine the sugar, butter, and milk. Heat over medium-high, stirring until the butter and sugar are melted.
Remove from heat and stir in the chocolate chips until smooth. Pour the icing over the cake and spread evenly.
Refrigerate the cake overnight to allow the topping to fully set.
The next day, loosen the edges with a knife and remove the springform ring.
In a medium bowl, whip the cream and brandy until soft peaks form.
Spread the whipped cream over the top of the cake and decorate with berries if desired. Chill until ready to serve.