Preheat oven to 350°F.
In a food processor, pulse chocolate cookies into crumbs. Place in a medium bowl and combine with melted butter and sugar. Press into bottom of a 9-inch springform pan. Place in oven and bake for 5 minutes, to set crust, the set aside to cool while you make the filling.
In a medium microwave-safe bowl, melt the chocolate in microwave 20-30 seconds at a time, stirring each time, until smooth. Set aside.
In the bowl of a stand mixer fitted with the paddle attachment (or a large bowl if using a hand mixer), mix cream cheese, sugar, cocoa powder, and vanilla until smooth, scraping sides of bowl as needed.
Add eggs, one at a time, mixing on low speed after each addition until just mixed. Do not overmix.
Mix in melted chocolate until combined. Pour cheesecake batter over crust and spread evenly with a spatula.
Bake for 50-60 minutes or until center is almost set. The center will still jiggle while edges will be set.
Turn oven off and crack oven door to allow cheesecake to cool slowly for 10 minutes, then remove cheesecake and allow to cool another 10 minutes. Use a sharp knife to run arond the edges to help release the cheesecake from the sides of the pan.
Allow cheesecake to cool at room temperature for at least an hour, then cover and refrigerate for six hours or overnight.
When ready to serve, release sides of springform pan and gently remove from the cheesecake. Top chilled cheesecake with cherry pie filling, keeping them more towards the center, so you have plenty of room around the edges for your whipped cream.
To make the whipped cream, combine heavy cream, sugar, and vanilla in a COLD mxing bowl and beat at high speed until thick, but still soft. Transfer to a piping bag with a decorative tip of choice, and pipe a decorative border around the cheesecake.
For extra decoration, add chocolate shavings or curls all over teh top of the cheesecake. You can use a vegetable peeler for curls or shavings or a zester for shavings/sprinkles.
Store airtight in the refrigerator for up to three days.