Chocolate Midnight Pie

Dark magic! This luxurious pie makes its own chocolate-sugar topping as it bakes. Based on an old Southern favorite, chess pie, its texture hits the sweet spot between cheesecake and custard. A dollop of chocolate-infused whipped cream (see "tips," below) takes it over the top.

Prep
20 mins
Bake
45 mins
Total
10 hrs 5 mins
Yield
9" pie, 8 to 12 servings
Chocolate Midnight Pie

Instructions

  1. To make the crust: Stir together the flour, sugar, and salt.

  2. Work the butter into the dry ingredients (using your fingers, a pastry blender or fork, or a mixer) until the dough is unevenly crumbly.

  3. Dissolve the espresso powder in 1 tablespoon of the milk. Sprinkle up to 5 tablespoons (or more, if necessary) of the milk into the dry ingredients (beginning with the tablespoon of espresso milk), continuing to mix until the dough is cohesive. Grab a handful; if it holds together willingly, and doesn't seem at all dry or crumbly, you've added enough liquid.

  4. Shape the dough into a disk. Roll its edges along a floured work surface (as though the disk were a wheel), in order to smooth them out. Pat the disk until it's about 1" thick, wrap it in plastic wrap, and refrigerate for at least 1 hour, or overnight.

  5. Preheat the oven to 350°F. Remove the dough from the refrigerator. Allow it to warm a bit and become flexible, 15 to 30 minutes

  6. Flour your work surface, and roll the dough into a 12" circle. Transfer the dough to a regular (not deep-dish) 9" pie pan that's at least 1 1/4" deep. Trim and crimp the edges. Place the crust in the refrigerator to chill, while you're preparing the filling.

  7. Beat together the butter, sugar, and salt until smooth.

  8. Add the eggs one at a time, beating slowly but thoroughly after each addition; you want to combine them with the butter and sugar, but not beat in a lot of air.

  9. Stir in the cocoa, liqueur, milk, and vanilla.

  10. Use a food processor (mini, if you have one) to grind together the espresso powder, cornmeal, and chocolate chips. Add to the batter. Pour the batter into the crust.

  11. Bake the pie for 45 minutes, adding a crust shield after 20 minutes. The middle may look pretty soft; so long as the temperature has reached 165°F right in the center, the pie is done. Note: If you're baking in a stoneware or glass pan, the baking time will almost certainly be a bit longer. Go by how the pie looks, not by your timer.

  12. Remove the pie from the oven, cool to room temperature, then cover and refrigerate overnight before serving.

  13. Serve each slice topped with a layer of whipped cream and a sprinkle of chocolate curls, if desired.

Tips from our Bakers

  • This pie is disturbingly liquid when you pull it out of the oven, but don't panic; an overnight rest in the refrigerator solidifies it and gives all the flavors a chance to mellow.
  • Plain whipped cream is a wonderful complement to this pie, but if you believe more chocolate is better, try this: whisk together 1/2 teaspoon espresso powder, 2 tablespoons Dutch-process cocoa, 1 tablespoon black cocoa, and 2 tablespoons confectioners' sugar in a medium heatproof bowl. Bring 1 1/4 cups heavy cream to a simmer and pour over the mixture, whisking until smooth. Stir one 1 teaspoon of vanilla extract and chill thoroughly before whipping. (If you don't have black cocoa, simply substitute additional Dutch-process.)