Preheat the oven to 325°F. Lightly spray a 9-inch springform pan with nonstick cooking spray and line it with parchment paper, including up the sides.
In a medium bowl, combine the Oreo cookie crumbs with the melted butter, mixing well with a fork. (You want every crumb coated in the butter as this will be the glue that holds it together.)
Press the crumbs into the bottom of the springform pan. Bake the crust for 10 minutes and set aside to cool.
To a microwave-safe bowl, add chocolate chips and ¼ cup of heavy cream. Heat in 20-second intervals, stirring in between until the chips have melted and the mixture is smooth with no lumps. Set aside while you make the filling.
In the bowl of a stand mixer with the paddle attachment, beat the cream cheese until creamy and smooth. Beat in the sugar and cocoa powder until smooth.
Add the eggs, one at a time. Pour in the remaining ½ cup of heavy cream, mixing until combined.
Remove the bowl from the stand mixer. Fold in the melted chocolate mixture. Add the vanilla and stir to combine. Pour the batter on top of the cooled cookie crust.
Bake for 65- 70 minutes. The cheesecake is done when the sides are set but the center is still a little bit jiggly.
Remove the cheesecake from the oven and let it rest at room temperature for an hour. Then, transfer the cheesecake to the refrigerator to chill for 2-4 hours, up to overnight.
Top the cooled cheesecake with the cherry pie filling, whipped cream, and chocolate curls/shavings.