Step 1: Prepare the Crust - Preheat your oven to 325°F (160°C). In a medium bowl, combine the finely crushed Oreo cookies and melted butter. Mix until the crumbs are well coated. Press this mixture firmly into the bottom of a 9-inch springform pan to create an even layer.
Step 2: Melt the Chocolate - In a double boiler or microwave-safe bowl, melt the chopped semi-sweet chocolate. If using a microwave, heat in 30-second intervals, stirring in between, until fully melted and smooth. Set aside to cool slightly.
Step 3: Make the Cheesecake Batter - In a large mixing bowl, beat the softened cream cheese with an electric mixer on medium speed until smooth and creamy, about 2-3 minutes. Gradually add in the granulated sugar and flour, mixing until well combined.
Step 4: Add Flavorings - Mix in the vanilla extract, followed by the eggs, one at a time, ensuring each is fully incorporated before adding the next. Pour in the milk and amaretto, mixing until the batter is smooth.
Step 5: Incorporate the Chocolate - Gently fold the melted chocolate into the cheesecake batter until combined, being careful not to overmix.
Step 6: Bake the Cheesecake - Pour the cheesecake batter over the prepared crust in the springform pan. Place the cheesecake in the preheated oven and bake for 55-60 minutes, or until the center is set but still slightly jiggly. Turn off the oven and leave the cheesecake inside for an additional hour to cool slowly, which helps prevent cracks.
Step 7: Chill and Serve - Once cooled, remove the cheesecake from the oven and let it cool to room temperature. Cover with plastic wrap and refrigerate for at least 4 hours or overnight. When ready to serve, top with toasted sliced almonds and a dollop of whipped cream.