In a mixing bowl, whip the heavy cream, powdered sugar, and vanilla extract together until soft peaks form. Be careful not to overwhip.
In serving cups or bowls, layer 1/4 cup of chocolate cake crumbs at the bottom.
Add a layer of 1/4 cup cherry pie filling on top of the cake crumbs.
Spoon a layer of whipped cream (about 1/4 cup) over the cherry filling.
Repeat the layers until the cups are filled, finishing with a layer of whipped cream on top.
Garnish with chocolate shavings and a fresh cherry, if desired.
Chill in the refrigerator for at least 30 minutes before serving to allow the flavors to meld.