Using a fork, toss the cookie crumbs, sugar, and melted butter together in a medium bowl. Press mixture into the bottom and up the sides of a 9-inch pie dish and refrigerate while you make the fillings.

In a the chilled bowl of a stand mixer, fitted with a whisk attachment, whip the heavy cream on high until soft peaks form. Add a 1/2 cup powdered sugar and the vanilla and continue beating until stiff peaks form. Transfer whipped cream to another bowl.

Return bowl to mixer and replace whisk attachment with paddle attachment. Beat the cream cheese and remaining 1 cup of powdered sugar together until smooth and creamy. Pour half of the cream cheese mixture into a separate bowl; set aside.

Add half of the whipped cream to the cream cheese mixture that's still in the mixer, beating until combined. Pour mixture into the crust, smoothing out into an even layer.

Add the reserved cream cheese mixture back into the mixing bowl. Combine the orange gelatin and boiling water, stirring until dissolved. Pour gelatin mixture into the cream cheese mixture, beating until smooth and combined. Make sure to scrape down the sides of the bowl between mixings so that the gelatin mixture doesn't solidify along the walls of the bowl.

Remove bowl from mixer and fold in the rest of the whipped cream. Pour orange filling on top of the vanilla cream filling, smoothing out with a spatula. Refrigerate for at least 6 hours, or overnight.

If desired, add a border of whipped cream and sprinkles to the pie. Slice into pieces, serve, and enjoy!