Preheat the oven to 350°F.
In a large bowl, mix chocolate cookie crumbs, butter, and sugar together. Press into the bottom of a 9-inch springform pan.
1 ½ cups crushed Oreos, 4 Tablespoons salted butter, 1 Tablespoon granulated sugar
Bake the crust for five minutes until set. Set aside to cool while making cheesecake.
Prepare cheesecake: In a medium microwave-safe bowl, combine milk and chocolate and heat in the microwave 20-30 seconds at a time, stirring each time, whisk until mixture is completely smooth. Set aside.
10 ounces bittersweet chocolate, ¾ cup milk
In a large bowl, mix cream cheese, sugar, cocoa powder, and vanilla using an electric mixer until smooth, scraping sides of bowl as needed.
3 (8-ounce) packages cream cheese, 1 ¼ cups granulated sugar, ¼ cup cocoa powder, 2 teaspoons pure vanilla extract
Add eggs, one at a time, mixing on low speed after each addition until just mixed. Don’t overmix.
4 large eggs
Mix in melted chocolate until combined. Pour cheesecake batter over the crust and spread evenly.
Bake for 50-60 minutes or until the center is almost set. The center will still jiggle while edges will be set.
Turn the oven off and crack the oven door to allow cheesecake to cool slowly for 10 minutes, then remove cheesecake and carefully run a sharp knife around the rim of the pan to loosen the cake.
Allow cheesecake to cool at room temperature for at least an hour, then cover and refrigerate for six hours or overnight.
Decoration: Release sides of springform pan. Top chilled cheesecake with cherry pie filling, mounding cherries toward the center.
1 (21-ounce) can cherry pie filling
In a medium bowl, combine cream, sugar, and vanilla and beat using an electric mixer until thick, but still soft. Transfer to a piping bag with a decorative tip. Pipe swirls around the border of cheesecake.
1 cup heavy cream, 3 Tablespoons powdered sugar, 1 teaspoon pure vanilla extract
If desired, make chocolate shavings or curls by placing a chocolate bar in a warm place (~78°F) for about one hour. Or alternatively, heat the chocolate bar in a microwave oven for 1-2 seconds. Using a vegetable peeler, shave chocolate bar into curls or shavings and place on cheesecake just before serving.
Chocolate curls