This was a dusty old post from the archives that I wrote nearly 9 years ago, and darn it this pie is so good that I wanted to give it a refresh and truly do it justice in a second go-round. If you’ve never had or heard of chess pie before, it hails from the southern states and its main characteristics are that it’s 1) a baked custard, and 2) has corn meal as the thickening agent in the custard instead of flour. Over the years of making this chocolate chess pie, I’ve started pulsing the corn meal in a blender or food processor to get it nice and fine, since most of the cornmeal you find at the store is coarsely ground and more geared towards polenta or heavy-crumbed cornbreads. Those few minutes of pulsing that corn meal into a fine powder have made all the difference in upping the silkiness factor of this custard base, and I highly recommend taking the few seconds to do so.

I’m a bit obsessed with salted chocolate, so I sprinkled some flakey sea salt over the pie once it was done, and the nice salted crunch against the sweet chocolate filling was very, very good. It’s a very small step that makes all the difference in terms of flavor and texture. And you probably noticed, but I dressed up the top a bit by making a crescent shape out of some extra pie crust dough. I have all the details on how to do this in the recipe below, and don’t worry, it’s a lot easier than it looks (don’t you just love things that look fancy but aren’t actually that difficult? I know I do!)

I hope you enjoy the recipe, my friends, and that it gives you something cozy and comforting to enjoy during the cold months ahead. Oh! And one more thing. The original post has a verrrrrry old giveaway in it for a set of cookbooks, and one of the entry requirements was to leave a comment about your favorite cookbook. So if you scroll down to the comments section, there’s LOADS of amazing cookbook recommendations for your viewing pleasure (maybe you can find some Christmas gift ideas in there, too!)

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Chocolate Chess Pie

Prep Time 25 minutes

Cook Time 50 minutes

Cooling Time 20 minutes

Total Time 1 hour 15 minutes

Author Eva Kosmas Flores

Ingredients

Chocolate Chess Pie Filling

• 2 Eggs beaten
• 5 ounces Evaporated Milk
• 1 Cup White Sugar
• 1/4 Cup Brown Sugar
• 1/4 Cup Cocoa Powder
• 1/4 Cup Butter melted
• 2 Tablespoons Finely Ground Corn Meal (Can pulse normal corn meal in a blender or food processor to make it extra fine)
• 1 Teaspoon Vanilla Extract
• 1 1/2 Teaspoons Flake sea salt, such as maldon salt

Pie Crust

• 2 3/4 Cups Flour
• 2 Tablespoons Granulated Sugar
• 1/2 Teaspoon Salt
• 8 ounces Unsalted Butter very cold
• 9 to 12 Tablespoons of Ice Water
• 1 egg
• 1 teaspoon milk

Instructions

Pie Crust

• Grease the pie pan, place it upside down on top of a piece of paper, and trace the circumference of the pan. Then nudge the pan a few inches to the side to reveal a crescent shape in the tracing. Trace the edge of the pan to create the crescent shape. Place the pan right side up again and set it aside.
• In a large bowl, mix together the flour, sugar, and salt until combined. Using a box grater, grate the butter using the large hole setting of the grater above the bowl, stopping to stir and coat the butter bits in the flour mixture every 10 seconds or so. When all the butter is in, pinch the mixture together with your fingertips until it resembles the texture of damp sand. Add the water, a tablespoon at a time, mixing it with a fork, until the dough just holds together when you squeeze a fistful of it in your hand.
• Divide the dough into two portions, one slightly larger than the other (about 1/3 vs 2/3). Roll out the larger quantity of dough until it is 1 cm thick and transfer it to the greased pie pan. Press the crust into the pan, trim off the excess leaving a 1-inch overhang. Fold the 1-inch overhang under the edge of the crust all the way around and pinch the edges. Cover and place the pan in the freezer for 30 minutes.
• Roll out the smaller dough until it's 1 cm thick. Cut out the traced crescent and place it over the dough. Use a pizza cutter, pastry cutter, or sharp paring knife to cut out the crescent shape. Discard the paper. Use cookie cutters or pie cutters to cut out more decorative shapes, or you can cut them out of the dough by hand with a knife.
• In a small bowl, whisk together the egg and milk to create the egg wash. Place a piece of parchment paper on a small baking sheet and place the crescent on top of it. Brush it lightly with the egg wash, and brush any decorative cut-outs with the egg wash. Arrange the decorative cut-outs on the crescent, and place the pan in the freezer for 45 minutes.

Chocolate Chess Pie

• Preheat the oven to 350 degrees Fahrenheit. In the bowl of a stand mixer fitted with the paddle attachment, mix together the granulated sugar, brown sugar, cornmeal, and cocoa powder at low speed. Add the eggs, one at a time, and mix until fully incorporated. Then mix in the evaporated milk, butter, and vanilla extract until completely combined.
• For the top decoration, place the baking sheet with the crescent on it in the oven and bake at 350 degrees until golden, about 30 minutes (it can be in the oven at the same time as the pie that follows). Allow the crescent to cool to room temperature.
• Pour the filling into the prepared pie crust and bake on the second lowest rack of the oven until the filling is set around the edges and the center has a *very* small wiggle to it, about 1 hour to 1 hour 10 minutes. (If the crust is browning too quickly, cover the edges with tin foil but don't let the tin foil touch the filling). Remove from the oven and allow to cool for 30 minutes before sprinkling with the flake sea salt, garnishing the top with the crescent, slicing the pie, and serving.