Start by beating your softened cream cheese in a large bowl until it’s smooth and fluffy. This should take about two minutes with a hand mixer.
Gradually pour in the sweetened condensed milk. Keep mixing on a low speed until the two are completely married together. There should be no streaks.
Stir in your peppermint extract and your red food coloring if you're using it. Start with one drop; you want "winter wonderland pink," not "neon highlighter pink."
In a separate, chilled bowl, whip your heavy cream until stiff peaks form. This is the secret to the height of the pie. Don't stop until the cream stands up on its own when you lift the beaters.
Gently fold the whipped cream into the pink peppermint mixture. Use a spatula and a light hand. If you stir too hard, you’ll deflate all that beautiful air.
Fold in about half of your crushed candy canes.
Pour the filling into your chocolate crust and smooth the top with a spatula.
Refrigerate for at least six hours, though overnight is much better for getting those clean, bakery-style slices.
Just before serving, sprinkle the remaining crushed candy canes over the top.