Step 1: Preheat your oven to 350°F (175°C). Wrap the bottom of a 9-inch springform pan tightly with several layers of heavy-duty aluminum foil to create a waterproof barrier for the water bath.
Step 2: For the crust, combine the chocolate cookie crumbs and ¼ cup granulated sugar in a medium bowl. Pour in the melted butter and mix until all crumbs are moistened. Press the mixture firmly into the bottom of the prepared springform pan. Bake for 8-10 minutes, then remove and let cool while you prepare the filling.
Step 3: Reduce oven temperature to 325°F (160°C). In a large bowl, beat the softened cream cheese with an electric mixer on medium speed until completely smooth and creamy, about 2-3 minutes. Make sure there are no lumps.
Step 4: Gradually add the 1 cup granulated sugar and cocoa powder to the cream cheese, beating on low speed until just combined, scraping down the sides of the bowl as needed.
Step 5: Beat in the eggs one at a time, mixing only until just combined after each addition. Stir in the vanilla extract. Gently fold in the melted and cooled semi-sweet chocolate until streaks disappear, being careful not to overmix.
Step 6: Pour the chocolate cream cheese filling over the cooled crust in the springform pan. Place the springform pan into a larger roasting pan. Carefully pour hot water into the roasting pan until it reaches halfway up the sides of the springform pan.
Step 7: Bake for 60-70 minutes, or until the edges are set but the center still jiggles slightly when gently shaken. Turn off the oven, prop the door open slightly, and let the cheesecake cool in the water bath for 1 hour.
Step 8: Carefully remove the springform pan from the water bath and transfer it to a wire rack to cool completely at room temperature. Once cool, cover loosely and refrigerate for at least 6 hours, or preferably overnight, until thoroughly chilled and set.
Step 9: Before serving, gently remove the sides of the springform pan. Spoon the cherry pie filling evenly over the top of the chilled cheesecake. Slice with a warm, clean knife and serve immediately.