Lightly grease the bottom and sides of a 9-inch springform pan.
In a large bowl, combine the crushed Oreo cookie crumbs (one regular full-size package), the melted unsalted butter (8 tablespoons), and 1/2 teaspoon espresso powder; mix until the crumbs are evenly moistened.
Press the crust mixture firmly into the bottom of the prepared pan, pressing it flat in the center and slightly up the sides. Place the crust in the freezer while you prepare the filling.
Set up a double boiler: fill a medium pot about one-third full with water and bring it to a low simmer over medium heat. Place a heatproof bowl on top of the pot so it sits above the water without touching it.
Put the 14 ounces coarsely chopped bittersweet chocolate into the heatproof bowl. Reduce heat to low and stir occasionally with a silicone spatula until the chocolate is completely melted.
Remove the bowl from the pot and stir in 1 and 1/2 teaspoons espresso powder. Set the melted chocolate aside to cool slightly (it should be warm, not hot, before adding to the filling).
In the bowl of a food processor (or a high-powered blender), pulse the 1 and 1/2 pounds (680 g) room-temperature cream cheese until completely smooth, scraping down the sides as needed, about 2 minutes.
Add the 1 cup (198 g) granulated sugar, 1/4 cup (53 g) packed light brown sugar, and 1 Tablespoon Dutch-process cocoa powder to the cream cheese; beat until smooth and fully combined.
Add 1 and 1/2 teaspoons vanilla extract and 1 cup (8 ounces) heavy cream to the mixture and mix just until combined (about 20 seconds).
Using a rubber spatula, fold the cooled melted bittersweet chocolate into the cream cheese mixture until evenly combined. Stir several times to ensure the filling is uniform.
Remove the crust from the freezer. Scrape the filling over the crust and smooth the top evenly.
Transfer the cheesecake to the refrigerator and chill until set, at least 6 hours.
While the cheesecake chills, make the ganache: place the 1 and 1/3 cups (226 g/8 ounces) finely chopped semi-sweet chocolate in a medium bowl.
In a small saucepan over medium heat, bring 1 and 1/4 cups (10 ounces) heavy cream to a low simmer. Pour about half of the hot cream over the chopped chocolate and let sit for 2 minutes.
Whisk the chocolate and cream together to melt and combine, then slowly add the remaining cream while whisking until the mixture is smooth and glossy.
Add the 1/4 cup (57 g) room-temperature unsalted butter (cut into cubes) to the ganache and stir with a spatula until the butter is completely melted and the ganache is smooth. Stir in 1 teaspoon espresso powder.
Reserve 1/2 cup of the ganache in a small bowl for piping. Keep the remaining ganache warm and pourable (allow it to cool slightly if it is too hot).
Pour the remaining ganache over the chilled cheesecake and smooth the top if needed. Sprinkle with chocolate shavings and/or espresso beans, if using.
Refrigerate the cheesecake until the ganache is set, about 1 hour.
Transfer the reserved 1/2 cup ganache to a piping bag fitted with a star tip. Pipe stars around the edge of the cheesecake and top each star with a few espresso beans, if desired.
To serve, slice the cheesecake with a thin-bladed sharp knife, wiping the knife clean between each cut.
Store the cheesecake loosely covered in the refrigerator for up to 4 days.