Prepare a 9-inch springform pan by lightly greasing the edges of the pan with cooking spray, and then wiping gently with a paper towel.
Grind the cookies into a fine crumb using a food processor or blender.
In a small bowl, melt the butter in the microwave for 30 to 45 seconds. Pour the melted butter over the cookie crumbs and stir until the crumbs are well coated.
Pour the crumbs into your springform pan and press firmly into the bottom and up on the sides to create a thick crust. Refrigerate or freeze the crust while you are preparing the filling.
Remove cream cheese from fridge. If you have time, allow it to come to room temperature. Otherwise, soften in the microwave for 15-20 seconds until soft but not melted. Beat on medium-high speed for 2 minutes until light and fluffy and free of any clumps. Add the heavy whipping cream and peppermint extract and beat for another 60 seconds. Scrape down sides of the bowl.
Chop the peppermint chocolate into small pieces and add into the cheesecake batter. Scrape down sides of the bowl as needed.
Add Cool Whip and mix until the cream cheese and Cool Whip are well combined. Add a drop of red food coloring and beat until incorporated.
Pour the cheesecake batter into the prepared Oreo crust.
Prepare the glaze by combining dark chocolate chips, corn syrup, butter and water in a microwave safe bowl. Microwave for 45-60 seconds. Stir vigorously until smooth. Pour the glaze over cheesecake.
Refrigerate for at least 3-4 hours.
Place the metal mixing bowl in the freezer for 5-10 minutes to chill. Pour the heavy whipping cream into the chilled bowl and use an electric mixer to beat the heavy cream on medium-high speed until the cream starts to thicken. Slowly add the powdered sugar and continue beating on high speed until stiff peaks form. Pipe the border of the cheesecake with whipped cream and top with Hershey’s Candy Cane Kisses.