In a large mixing bowl, beat cream cheese, milk, powdered sugar, and vanilla until smooth.
In a small microwave-safe bowl, heat chocolate for 30 seconds, stir, and then continue heating at 15 second intervals until melted and smooth. Be careful not to overheat, or the chocolate will scorch.
Allow chocolate to cool 3-4 minutes.
Slowly, in dollops, add the chocolate to the mixing bowl, beating until combined and smooth.
Fold in 1/2 tub of Cool Whip or whipped topping (eyeball it). Reserve remaining for garnish.
Spread the chocolate mixture into the bottom of the pie crust, taking care not to "lift" any portions of the crust as you spread.
In a large bowl, whisk together vanilla pudding mixes, milk, pumpkin, and spices until smooth.
Carefully spread the pumpkin mixture over the chocolate layer.
Using a star tip, pipe the remaining Cool Whip around the edges. Garnish with chocolate chips, chocolate curls, and/or chocolate sauce, if desired.
Refrigerate for at least 2 hours, or until firm. Cut and serve.