Center a rack and preheat the oven to 325°F. Line the bottom and sides of a 9-inch springform pan with parchment, then wrap the outside of the pan tightly with two layers of heavy-duty aluminum foil to protect it from water.
Make the crust: Pulse the Oreo cookies (wafers + filling) in a food processor until they are fine crumbs. Stir in the melted butter until the mixture resembles wet sand.
Press the cookie mixture firmly into the bottom of the prepared springform pan and slightly up the sides (about 1/4 inch). Chill the crust in the fridge while you prepare the filling, about 10–15 minutes.
Prepare the batter: In a large bowl, beat the room-temperature cream cheese and sugar together on medium speed with an electric mixer until smooth and free of lumps, about 2–3 minutes. Scrape the bowl well.
Add the cocoa powder and beat again briefly to combine. Lower the mixer speed and add the sour cream, then the buttermilk, vinegar, and vanilla; mix until evenly blended.
Stir in the red food coloring until the batter reaches an even, vibrant color. With the mixer on low, add the beaten eggs in three short additions, mixing just until each addition is incorporated to avoid overworking the batter.
Pour the filling onto the chilled Oreo crust and smooth the top with an offset spatula. Tap the pan gently on the counter to release any large air bubbles.
Place the wrapped springform pan in a large roasting pan. Pour boiling water into the roasting pan until it comes about 1 inch up the sides of the springform pan to create a gentle water bath.
Bake at 325°F for 60–70 minutes, or until the edges are set and the center still has a slight wobble (like soft jelly). Reduce oven temperature to 300°F after 40 minutes if the top is browning too much.
Turn off the oven and crack the door. Let the cheesecake cool in the oven for 45 minutes to an hour — this gradual cooling helps prevent cracks. Afterward, remove the cheesecake from the water bath and unwrap the foil. Cool to room temperature on a rack, then refrigerate at least 6 hours or overnight.
Make the ganache: place the chopped dark chocolate in a heatproof bowl. Heat 1/2 cup heavy cream just to a simmer, pour over the chocolate, let sit 2–3 minutes, then whisk to a glossy ganache. If needed, warm gently in 10-second bursts in the microwave and whisk smooth.
Remove chilled cheesecake from the fridge and run a thin knife around the edge to loosen. Unlock the springform and lift off the ring. If any condensation has formed on the surface, blot gently with a paper towel.
Pour the ganache over the top, spreading to the edges and allowing an elegant drip down the sides. Chill for 15–30 minutes until the ganache sets slightly.
Whip the remaining 1/2 cup heavy cream to soft peaks and transfer to a piping bag fitted with a star tip. Pipe rosettes around the edge of the cheesecake, then sprinkle the chopped Oreos across the top. Keep chilled until serving.
To slice cleanly, dip a thin knife in hot water, wipe dry, and make each cut in one smooth motion, wiping the blade between cuts.