In a chilled mixing bowl, beat heavy cream, powdered sugar, and vanilla extract until stiff peaks form.

Distribute half of the chocolate cake crumbs evenly among four dessert glasses or jars.

Top the cake layer with two tablespoons of cherry pie filling in each glass.

Pipe or spoon a layer of the whipped cream over the cherries.

Repeat the layers by adding the remaining cake crumbs, followed by the remaining cherry filling.

Add a final layer of whipped cream to the top of each cup.

Garnish with dark chocolate shavings and a single cherry on top.

Refrigerate for at least 30 minutes before serving to allow layers to set.