Preheat the oven to 300F/149C. Wrap the bottom of a 9-inch (23-cm) springform pan with two layers of extra wide foil in preparation for the water bath. Spray the sides of the pan with a baking spray, then set it aside.
Making the Cookie Crust:
Next, prepare the chocolate cookie crust. Place the cookies into a food processor and pulse for about a minute, until fine crumbs form. Next, pour in the melted butter and pulse again until the crumbs are well coated.
Transfer the cookie crumbs into your prepared springform pan. I like to use a potato masher to press the crumbs firmly into the bottom of the spring form pan. The crust is ready!
Making the Cheesecake:
Once you have the chocolate cookie crust prepared, it’s time for the cheesecake batter. Place the softened cream cheese into a mixer bowl and attach a flat beater. Beat the cream cheese on medium speed for 7 to 9 minutes, until it’s cream and smooth. Scrape down the sides of the mixing bowl periodically.
Next, melt the semi-sweet chocolate chips in the microwave or on the stove top, using a double boiler. Add the melted chocolate to the cream cheese, along with the sour cream, cocoa powder, vanilla extract, and sugar. Beat everything together for a 2 to 3 minutes, scraping down the sides of the mixing bowl.
Next, add in the eggs, one a time with the mixer running on medium speed. Beat for about 2 minutes, stopping halfway to scrape down your mixing bowl.
Pour the prepared cheesecake batter into the springform pan. Tap the pan a few times against your work surface to settle the batter, then level it with an offset spatula. The cheesecake is ready for the oven!
Baking the Cheesecake:
Make sure your springform is wrapped in foil! Place the cheesecake onto a large baking sheet and fill the baking sheet to the top with water. This is easier to do with the baking pan on your oven rack.
Bake the cheesecake at 300F/149C for 2 hours, then turn the oven off and prop the oven door open with a wooden spoon. Allow the cheesecake to cool slowly for a few hours before transferring it into the refrigerator to chill overnight.
Making Cherry Whipped Cream:
Pour very cold heavy cream into a medium sized mixing bowl. Add the vanilla extract, cherry liqueur or extract, and powdered sugar.
Start whisking the cream on slow speed, gradually increasing it, and whisk the cream for 4 to 5 minutes, until stiff peaks form. Transfer the whipped cream into a pastry bag tipped with a star tip. I used Ateco tip #847.
Assembling the Cheesecake:
Release the springform pan, then use a flat spatula to loosen the cheesecake from the pan by sliding it underneath the crust. Watch my video tutorial to see how it’s done. Carefully transfer the chocolate cheesecake onto a cake stand.
Pipe generous dollops of whipped cream around the edge of the cheesecake. This will help keep the cherry pie filling on the inside. Add the pie filling into the center and spread it evenly to the whipped cream.
This cheesecake can be served right away, or keep in the refrigerator for a day or two. Serve the cake with extra whipped cream on the side. You can also freeze the ungarnished/untopped chocolate cheesecake for 1 month. Wrap the cake well in plastic before freezing.