In a large blender, combine the heavy whipping cream, cooled brewed coffee, powdered sugar, cocoa powder, vanilla extract, and the instant vanilla pudding mix.
Blend on a low to medium speed until the mixture is smooth and begins to thicken, about 1-2 minutes. If you have a smaller blender, you may need to do this in two batches.
Immediately pour the mixture evenly into four parfait glasses or small dessert bowls.
Let the pudding sit for at least 5 minutes to allow it to fully set and firm up.
Just before serving, garnish each pudding with a generous dollop of whipped cream and a maraschino cherry or a sprinkle of chocolate shavings.
Don't over-blend!
Mix just until the are combined and the pudding starts to thicken. Over-mixing can sometimes make the mixture too dense.