Chocolate Chess Pie

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Chocolate chess pie is a traditionally Southern dessert with a slightly crisp and crackly top layer that leads to a rich and luscious brownie-like center. Serve this perfectly chocolatey pie just a touch warm with whipped cream, ice cream, or as is.

Every year, for the past 6 years, I’ve hosted a monthly recipe around a central theme.

In 2017, I featured a monthly cake recipe. In 2018, muffins were on the menu. In 2019, it was all about the breads. In 2020, I featured 12 delicious brownie recipes. Then, in 2021 the theme was all things no bake.

Now, in 2022 I’m featuring a new pie every single month. So far, I’ve shared banoffee pie and now, this chocolate chess pie.

I noticed a serious misrepresentation of pies on my site, so the only remedy of course was to bring you more fantastic pies to delight in every month.

Second on the docket is this rich, fudgy, and totally easy chocolate chess pie. Let’s get started!

Like so many traditional Southern recipes, chocolate chess pie is made with just a few basic ingredients and is what you think of when you hear the idiom “easy as pie.” As a heads up, not all pie is easy. But this one? It’s a total cinch!

One legend goes that when someone asked what the pie was called, its baker replied (in her thick Southern accent), “jus’ pie,” which was mistaken for “chess pie.”

Another story claims that the original pie was named chess pie after the word “chest,” which was in reference to the pie and ice chests used at the time. Since the ingredients were mostly shelf-stable and easily available, the pie could be stored in a for a good while without spoiling.

Ice chests were not at all like our modern freezers, and instead held the temperature of a slightly warm fridge, so having a tasty dessert that would store well in one of these was a real treat!

Yet another version claims that the pie was given its name from its place of origin, which was Chester, England. Since the pie resembles so much of England’s custard-based desserts, it was assumed that the Southern classic must have made its way over the ocean.

And finally, a fourth story claims that the original pie used chestnut meal in place of the cornmeal, which has been used as a thickener in some recipes, the lemon version in particular.

This version, a decadent chocolate rendition, is one of the many flavors that were inspired by the original chess pie. Its custard-like filling and rich, chocolatey decadence bring it into a league of its own, while still keeping its humble chess pie roots.

While you can totally use store bought pie crusts if you want to, I promise you that making your own pie crust is actually SO simple once you have the technique down. And the taste? Well, you just can’t beat it!

For your homemade pie crust you’ll need some flour, sugar, salt, cold butter, cold shortening, and some ice water. Yes, that’s it!

And since my pie crust recipe makes a double crust pie, you’ll have to find a way to use up that extra pie dough. While you could totally freeze the other half for later, I can’t recommend my pie crust cookies enough. Or you could always make a batch of my pecan pie tarts, which are perfect year round (no matter what anyone else tries to tell you).

To make our chocolate chess pie, well, chocolate, we use a some cocoa powder. That’s right, no gentle tempering of baking chocolate required. This is a really simple and economical pie!

Some people even make their chocolate chess pie with sweetened condensed milk, but that’s a little too thick for my liking. Plus, it’s really hard to control how sweet your pie is when you use a presweetened ingredient like that.

Yet another option is to make chocolate chess pie with buttermilk, which is a staple in Southern style cooking.

Since every baker likes to put their unique twist on a recipe, there are countless variations of the basic chocolate chess pie recipe. I’m sold on using evaporated milk, since it results in that just right consistency that can’t be found with versions made with thinner buttermilk, or thicker sweetened condensed milk.

Once your pie crust is filled, you’ll want to cover the edges with some aluminum foil or a pie shield. This will prevent the edges from burning during baking, which can easily happen if they are left exposed to the heat of the oven for an extended period of time.

Give it a good whisk until everything is combined, smooth, and free from lumps.

Then go ahead and pour that decadent yumminess into the prepared pie crust and add some foil or a pie shield to the edge of the crust.

Then, place the pie on the center rack of the oven and bake for 50-55 minutes, ensuring to remove the foil/shield during the last 15 minutes of baking to give the crust a chance to get that beautiful golden brown color.

Don’t worry about a toothpick coming out clean. You’ll just want to examine the pie on the surface level, since the filling itself won’t be completely firm like other pies. It will firm up a bit during the cooling time, but think of it as a sort of fudgy brownie consistency and you’ll understand what I mean.

Once the chess pie is done baking, remove it from the oven and allow it to cool on a wire rack until it has completely cooled to room temperature.

If your Southern chess pie is a little too liquidy for your liking, you can place it in the fridge for a few hours, which will help the filling thicken up. This is just a matter of preference, so do whatever you like!

I happen to like mine ultra fudgy and rich, but if you prefer something on the firm side, go ahead and chill it for a few hours first.

Serve it with a big dollop of homemade whipped cream, some vanilla ice cream, or a big glass of cold milk. Or, if you’re like me: all of the above!

If you love the winning combo of chocolate and pecan, I highly (highly) recommend serving it with a big scoop of my homemade praline ice cream. You will not be disappointed, I promise.

To freeze your chess pie, wrap it tightly in plastic wrap and place it in a large freezer bag. Remove the air, and store towards the back of the freezer. Then, when you’re ready to serve, let it thaw in the refrigerator overnight. Go ahead and slice and serve as you would with the freshly baked version.

I hope you’re enjoying my year of pies thus far, I know I am! We kicked the year off with banoffee pie, and now we are in chocolate pie heaven with this recipe for chocolate chess pie. The year is just getting started, and we have lots of deliciousness ahead.