Homestyle Chocolate Chess Pie

Featured in: Homestyle Baking

Enjoy a bake of classic Southern comfort with this chocolate chess pie. Its fudgy, silky chocolate custard is nestled in a tender, buttery pie shell and finished with a billowing cloud of fresh whipped cream. Each bite offers a luscious blend of crisp crust and decadent chocolate, with just the right amount of sweetness. Simple steps and common ingredients make this dessert easy for any home cook, inviting warmth and nostalgia to every slice. Perfect for sharing with friends or family on any occasion.

Updated on Tue, 30 Sep 2025 08:56:58 GMT
Decadent slice of Homestyle Chocolate Chess Pie topped with fluffy whipped cream, ready to eat. Save
Decadent slice of Homestyle Chocolate Chess Pie topped with fluffy whipped cream, ready to eat. | forkina.com

This rich and fudgy chocolate chess pie brings Southern comfort food tradition right to your table with its silky smooth filling and buttery crust. The contrast between the dense chocolate custard and light whipped cream creates a perfect balance that makes this dessert irresistible for any occasion.

I first made this chocolate chess pie for a potluck dinner where I needed something foolproof but impressive. The look on my friends' faces when they took their first bite told me everything I needed to know this would become my signature dessert for years to come.

Ingredients

  • For the Pie Crust: Store bought or homemade 9 inch pie shell saves time without sacrificing quality. Look for all butter crusts if purchasing for the best flavor.
  • For the Chocolate Chess Filling: Granulated sugar creates the signature crackly top that chess pies are known for
  • : Large eggs provide structure and richness to the custard filling
  • : Unsweetened cocoa powder gives deep chocolate flavor without added sweetness. Dutch processed works best for a smoother taste
  • : Unsalted butter adds richness and helps create the fudgy texture. Make sure it's melted but not hot
  • : Evaporated milk creates a silky texture that regular milk cannot achieve
  • : Vanilla extract balances the chocolate flavor. Use pure not imitation for best results
  • : Salt enhances all the flavors and balances sweetness
  • For the Whipped Cream: Heavy cream should be very cold for the best volume when whipping
  • : Powdered sugar dissolves easily and stabilizes the whipped cream
  • : Vanilla extract adds warmth and complements the chocolate filling

Instructions

Prepare the Oven and Crust:
Preheat your oven to exactly 350°F. Place your pie shell in a 9 inch pie pan and take time to create a decorative crimped edge which not only looks beautiful but helps hold in the filling. The crust does not need to be prebaked for this recipe.
Mix the Dry Ingredients:
In a large bowl whisk together the sugar eggs and cocoa powder until completely smooth with no cocoa lumps remaining. This step is crucial as any unmixed cocoa will create bitter spots in your finished pie. The mixture should be thick and glossy when properly combined.
Incorporate Wet Ingredients:
Add the melted butter to your mixture ensuring it has cooled slightly so it doesn't cook the eggs. Pour in the evaporated milk vanilla extract and salt whisking continuously until the mixture becomes silky smooth and has a uniform chocolate color. The filling will be somewhat thin but will set during baking.
Fill and Bake:
Pour the chocolate filling carefully into your prepared pie shell. Fill it nearly to the top as the filling won't rise much during baking. Bake for 35 to 40 minutes watching closely toward the end. The perfect chess pie should have a slightly wobbly center when done as it will continue to set as it cools. The top will develop characteristic cracks which are the hallmark of a perfect chess pie.
Cool Completely:
Allow the pie to cool completely on a wire rack for at least 2 hours. The filling needs this time to fully set and develop its fudgy texture. Rushing this step will result in a filling that's too loose to slice cleanly.
This image shows a close-up of the beautiful Homestyle Chocolate Chess Pie, perfect for dessert tonight. Pin it
This image shows a close-up of the beautiful Homestyle Chocolate Chess Pie, perfect for dessert tonight. | forkina.com

Chess pies have been a staple in Southern kitchens for generations and I remember my grandmother making this exact recipe every Christmas. The evaporated milk is truly the secret ingredient here. I once tried substituting regular milk in a pinch and while still good the texture was never quite as silky smooth as the original version.

Storage Tips

This chocolate chess pie will keep beautifully at room temperature for up to 2 days if covered with a cake dome or inverted bowl. For longer storage refrigerate the pie for up to 5 days but always bring it to room temperature before serving for the best flavor and texture. The cold dulls the chocolate notes that make this pie special.

If you need to store leftover whipped cream keep it separately in an airtight container in the refrigerator for up to 2 days. It may need a quick rewhip before serving again to restore its fluffy texture.

Ingredient Substitutions

No evaporated milk? You can substitute half and half or even full fat coconut milk for a dairy alternative that maintains the creamy texture.

For a gluten free version simply swap in your favorite gluten free pie crust. The filling itself contains no gluten.

Dark chocolate lovers can add a tablespoon of instant espresso powder to the filling which deepens the chocolate flavor without adding coffee taste.

Serving Suggestions

While delicious on its own this chocolate chess pie reaches new heights with thoughtful accompaniments. Serve with fresh berries particularly raspberries whose tartness cuts through the rich chocolate.

For an elevated presentation dust each slice with cocoa powder through a fine mesh sieve just before serving or add chocolate curls on top of the whipped cream.

For a truly decadent experience warm individual slices for 15 seconds in the microwave and serve with a scoop of vanilla ice cream alongside the whipped cream.

The History Behind Chess Pie

Chess pie has deep roots in Southern American cuisine dating back to the 1700s. The name's origin remains debated with some claiming it derived from cheese pies without cheese while others suggest it came from pie safes called "chest pies." The chocolate variation emerged later as cocoa became more accessible to American households.

Traditional chess pies feature a simple custard of eggs butter and sugar that creates a caramelized top and gooey center. This chocolate version maintains those beloved characteristics while adding rich cocoa flavor that transforms the humble pie into something truly special for chocolate lovers.

A slice of rich Homestyle Chocolate Chess Pie with a creamy, custardy texture, ready to serve. Pin it
A slice of rich Homestyle Chocolate Chess Pie with a creamy, custardy texture, ready to serve. | forkina.com

Homestyle Chocolate Chess Pie

Southern chocolate custard in flaky crust with airy whipped cream. Rich, easy treat perfect to share.

Prep Time
20 Minutes
Cook Time
40 Minutes
Total Time
60 Minutes

Category: Homestyle Baking

Difficulty: Easy

Cuisine: American (Southern)

Yield: 8 servings

Dietary: Vegetarian

Ingredients

For the Pie Crust

01 1 unbaked 9-inch pie shell

For the Chocolate Chess Filling

01 1 1/2 cups granulated sugar
02 3 large eggs
03 1/4 cup unsweetened cocoa powder
04 1/2 cup unsalted butter, melted and slightly cooled
05 1/2 cup evaporated milk
06 2 teaspoons vanilla extract
07 1/4 teaspoon salt

For the Whipped Cream

01 1 cup heavy cream, cold
02 2 tablespoons powdered sugar
03 1 teaspoon vanilla extract

Instructions

Step 01

Preheat Oven and Prepare Crust: Preheat your oven to 350°F (175°C). Place the unbaked 9-inch pie shell in a 9-inch pie pan and crimp the edges. Set aside.

Step 02

Mix the Chocolate Filling: In a large mixing bowl, whisk together the granulated sugar, eggs, and unsweetened cocoa powder until the mixture is smooth and well combined. Incorporate the melted butter, evaporated milk, vanilla extract, and salt, whisking until all ingredients are fully integrated.

Step 03

Fill and Bake the Pie: Pour the prepared chocolate filling into the seasoned pie shell. Transfer the pie to the preheated oven and bake for 35 to 40 minutes. The center should be just set, with a slight wobble. Minor cracking on the surface is expected.

Step 04

Cool the Pie: Remove the pie from the oven and place it on a wire rack to cool completely.

Step 05

Prepare Whipped Cream: While the pie cools, prepare the whipped cream. In a chilled mixing bowl, use an electric mixer or hand whisk to beat the cold heavy cream, powdered sugar, and vanilla extract on medium-high speed until soft peaks form.

Step 06

Serve: Once the pie has cooled, slice it and serve each portion with a generous dollop of the freshly whipped cream.

Tools You'll Need

  • 9-inch pie pan
  • Mixing bowls
  • Whisk
  • Electric mixer or hand whisk
  • Measuring cups and spoons
  • Wire rack

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.
  • Contains: Eggs, Milk. May contain Wheat depending on the pie crust used.
  • Carefully review labels of store-bought ingredients, such as pie crust and evaporated milk, to identify any hidden allergens.

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: 410
  • Total Fat: 24 g
  • Total Carbohydrate: 48 g
  • Protein: 5 g