Make the caramel sauce: In a large heavy-bottomed pot over medium heat, add 1 cup (200g) granulated sugar in an even layer. Cook without stirring (occasionally swirl the pan if needed) until the sugar is completely melted and reaches a light amber color.
Reduce the heat to low and carefully add ½ cup (120ml) heavy cream (the sugar will bubble vigorously). Stir until the mixture is smooth.
Add 75g unsalted butter (cut into 6 pieces) and stir until fully melted and the sauce is smooth. Remove from the heat, stir in 1 teaspoon (5ml) pure vanilla extract and ¼ teaspoon salt. Transfer the caramel to a heatproof bowl or jar and let cool at least 30 minutes before using.
Preheat the oven to 350°F (180°C). If using a fan/convection oven, use 160°C.
Make the crust: In a food processor, pulse 24 regular whole Oreo cookies (one 9.5 oz / 270g package) until they are fine crumbs. Add ¼ cup (56g) melted unsalted butter and pulse until the mixture resembles wet sand.
Press the crumb mixture into the bottom (and slightly up the sides) of a 9-inch springform pan. Use the bottom of a measuring cup or a glass to press the crumbs firmly and evenly.
Wrap the bottom and sides of the springform pan with two large pieces of aluminum foil so the seams are covered and the pan is watertight.
Bake the crust in the preheated oven for 10 minutes. Remove and cool on a wire rack for 15 minutes. Lower the oven temperature to 325°F (160°C) (140°C for a fan oven).
Make the cheesecake base: In a large mixing bowl, beat 32 ounces (900g) cream cheese (softened to room temperature) with 1 cup (200g) granulated sugar and 2 tablespoons (15g) all-purpose flour until smooth and no lumps remain.
Add 4 large eggs, one at a time, mixing gently and scraping down the bowl between additions. Add ½ cup (125g) sour cream and 1 teaspoon (5ml) pure vanilla extract and mix until fully combined.
Divide the cheesecake batter evenly into two bowls (two equal portions).
Prepare the chocolate for one portion: Melt 4 ounces (113g) semi‑sweet chocolate and let it cool to warm/room temperature. Stir the melted chocolate into one portion of batter until smooth.
Stir 80ml caramel sauce (from step 3) into the other portion of batter until smooth.
Assemble the layered cheesecake: Sprinkle ¼ cup finely chopped pecans evenly over the cooled crust.
Spoon half of the caramel cheesecake batter over the pecans and crust, spreading gently to cover.
Spoon half of the chocolate cheesecake batter in 5–6 dollops over the caramel batter and use a butter knife to swirl the dollops into the caramel (do not overmix).
Sprinkle the remaining ¼ cup finely chopped pecans over the swirled layer.
Spoon the remaining caramel batter over the pecans, then spoon the remaining chocolate batter in 5–6 dollops and swirl again with a butter knife to create a marbled top.
Place the foil-wrapped springform pan into a large roasting pan. Carefully pour hot water into the roasting pan to come 1–2 inches up the sides of the springform pan (bain-marie).
Carefully transfer to the preheated oven and bake at 325°F (160°C) for 50–60 minutes, or until the edges are set and the center still has a slight wobble when the pan is gently shaken.
Turn the oven off and crack the oven door open. Let the cheesecake cool in the oven for 1 hour.
Remove the cheesecake from the oven, take it out of the water bath, remove the foil, and let it cool uncovered on a wire rack until completely cool (about 1 hour). Refrigerate the cheesecake for at least 6 hours or overnight.
After chilling, run a thin butter knife around the edge of the pan to release the cheesecake, then remove the sides of the springform pan and transfer the cheesecake to a serving plate if desired.
Make the chocolate ganache: Place 3 ounces (85g) semi‑sweet chocolate (or ½ cup chocolate chips) in a medium heatproof bowl. Heat ¼ cup (60ml) heavy cream until steaming (do not boil). Pour the hot cream over the chocolate, let sit 1 minute, then stir until smooth. Let the ganache cool slightly, then spread evenly over the chilled cheesecake.
Make the whipped cream: In a large chilled bowl, combine 1 cup (240ml) very cold heavy whipping cream, ½ cup powdered sugar, and 1 teaspoon (5ml) pure vanilla extract. Whip on high speed until stiff peaks form.
Pipe or spread the whipped cream around the outside edge of the cheesecake as a border.
Finish the cheesecake by drizzling ¼ cup (60ml) caramel sauce (from step 3) over the top and sprinkling with the remaining ¼ cup finely chopped pecans.
Keep the finished cheesecake refrigerated until ready to serve.