Preheat the oven to 450 degrees F. Roll a store-bought or homemade pie crust out on a floured work surface, into a 14-inch circle. Hold one side of the pie crust over the rolling pin and carefully roll it over the top of the rolling pin to transfer it to a deep-dish pie pan. Don't stretch the pie crust, but gently move it into the center of the pie pan. Turn the edges underneath and crimp the edges to seal. Do this with a fork or with your fingers.
Place a large piece of foil or parchment paper over the pie crust and gently shape it over the dough. Fill the foil with ceramic pie weights, or dried beans. Bake the crust for 10-15 minutes. Take out of the oven and cool completely. Remove the foil and weights.
Once the pie crust is cool, pour the heavy cream in the bowl of a stand mixer with a whip attachment. Add 1/3 cup brown sugar and beat on high until whipped to firm peaks. Scoop the whipped cream out of the mixing bowl and refrigerate until ready to use.
Next place the cream cheese, remaining 1/3 cup brown sugar, and cinnamon in the stand mixing bowl. Beat on high to soften the cream cheese. Then turn on low and alternate adding the instant pudding powder and the milk, until both are well combine and the mixture is smooth.
Scrape the bowl with a spatula. Then beat again to make sure the mixture is completely smooth. Scoop half of the whipped cream into the pudding mixture. Gentle fold it in with a spatula until the mixture is light and even. Then scoop the filling into the prepared pie crust and spread out evenly.
Top the pie with the remaining whipped cream and sprinkle with extra cinnamon. Chill for at least 4 hours, or until ready to serve.