FOR THE GANACHE FILLING, add the chocolate to a heatproof bowl. Bring 2 1/2 cups cream to a simmer in a medium saucepan. Pour the cream over the chocolate and let the mixture sit for 1-2 minutes. Add the vanilla and whisk to combine until the mixture is glossy and smooth. Cover with plastic wrap and refrigerate until completely chilled, 2-3 hours.
When thoroughly chilled, scrape the mixture into an electric stand mixer fitted with the paddle or whisk attachment (or use a handheld electric mixer) and whip until the ganache is fluffy and lighter in color, about 1-2 minutes, scraping down the sides of the bowl as needed.
In a small bowl or in a blender, combine the softened cream cheese and remaining 1/2 cup cream and whip or process until smooth and thick.
Add the cream cheese mixture to the ganache filling and whip on low speed until combined and no white streaks remain.
Spread the chocolate filling in the baked and cooled pie crust.
FOR THE WHIPPED CREAM TOPPING, combine the whipping cream, powdered sugar and vanilla in a blender (or in a bowl using a handheld electric mixer or an electric stand mixer) and mix until thick and fluffy.
Spread the whipped cream topping over the pie.
If desired, grate chocolate over the top of the pie using a rasp grater or the small/poky holes of a box grater (or garnish with chocolate curls). Serve immediately or refrigerate for 2-3 hours before serving.