Chocolate Chess Pie

Chocolate Chess Pie

Every so often, I’ll become obsessed with a dessert recipe that I’ve never actually tried before. But I’ll be hooked anyway because of the way the dessert looks or sounds—like this chocolate chess pie. Katie S., a reader of mine from Virginia, specifically emailed me to request a chocolate chess pie recipe. She described her favorite version of it as “a big round brownie enveloped in a buttery pie crust.” Immediately, I was sold.

What is Chocolate Chess Pie?

But what even is chess pie, anyway? Although chess pies are most commonly found in the Southern United States, some food historians think that the original recipe came from mid-18th century England. The first cookbook that ever published a chess pie recipe described it as a cheesecake-like filling, but made without the cheese. Indeed, cheesecakes and chess pies share almost all the same ingredients—with the exception of cream cheese, both contain common baking ingredients like eggs, sugar, and butter. 

Over time, bakers experimented and came up with many different chess pie variations. There are chess pies made with different types of milk like buttermilk and evaporated milk for flavor; others with cornmeal and flour for a thicker textured custards. And of course, there are different chess pie flavors too: vanilla, buttermilk, vinegar (more on that in a second), and chocolate chess pies are probably the most common variations. In fact, one of the most popular desserts in the last decade, Milk Bar’s Crack Milk Bar Pie, is actually a very modern-take on a traditional chess pie. 

So why is it called chess pie?

It seems that nobody can agree on why chess pies are called chess pies. But there are three main prevailing theories on how chess pies got their name:

1. An Americanization of the English word “cheese”.
   I mentioned earlier that chess pies actually originated in England. In England, pies with curd fillings are often referred to as “cheese pies”. Some folks think that the word “cheese” was Americanized into the word “chess”.
   
   
2. The word “chess” is a reference to the way folks used to store food.
   Back in the day before modern refrigerators and freezers were invented, folks used to store their food in chest drawers that they called “chests”. The name chess pie is allegedly a reference to this, especially since chess pie recipes are often made with ingredients like eggs, butter, and cream that are prone to spoilage. To prevent food waste, folks would take these ingredients and bake them with a ton of sugar (which helped keep them going for longer, since sugar can act as a preservative), resulting in the very first chess pie. And bonus fact: the longer the chess pie sat in the chest, the more flavorful it got (similar to how some loaf cake and brownie recipes become more flavorful overnight as the ingredients fully meld together and absorb each others’ flavors). 
   
   
3. “Oh, it’s jes’ pie.”
   Another story is that the name chess pie originated from 19th-century Alabama, where a freed slave made a living selling pies to her neighbors. When no other seasonal ingredients like pecans or fruit were available, she made a sugar pie out of the only available ingredients: eggs, sugar, flour, and butter (a.k.a., the ingredients of almost every chess pie). When asked what kind of pie she was selling, the woman replied “Oh, it’s just pie.” Her Southern accent made it sound like, “Oh, it’s jes’ pie,” which folks then interpreted as “chess pie”. 

What Does Chocolate Chess Pie Taste Like?

As much as I personally love food history and can spend all day geeking out on it, I know most of you guys probably just have one question: that’s nice and all, but what does chess pie actually taste like?

Although regular chess pies can vary greatly in flavor depending on the ingredients they use (more on that in a second), I really liked the way Katie described the chocolate chess pie recipe she wanted. So when I set out to develop my own chocolate chess pie recipe, I knew I wanted the chocolate filling to be very similar to my favorite fudge brownie recipe: super chocolatey, dense and incredibly gooey. My favorite brownie also has a signature top that shines and crinkles like delicate paper—I wanted to see if I could make that work in my chocolate chess pie recipe, too.

But instead of the pie filling setting into a delicate paper top like my brownies, its top baked up as something else: a crisp, meringue-like chocolate top that cracked dramatically and beautifully as it cooled to room temperature. At first I worried that I’d overbaked the pie; I worried that the filling would be hard too. But a slice revealed that the inside was perfectly fudgy and gooey like a brownie—there was no sign of being overdone at all! If anything, it seemed a little undercooked. Together, the gooey filling and the meringue-like top was incredible and utterly addicting. I found myself sneaking bites so often that, by the time I realized how much I’d actually eaten, almost half the pie was gone. 

And finally, all of this decadent chocolate chess pie filling would be held in place by a super flaky and flavorful all-butter pie crust. 

Ingredients for Chocolate Chess Pie

Now that I’ve hopefully convinced you to make chocolate chess pie, I wanted to talk about the ingredients I used in my recipe and why I chose the ones that I did:

Chocolate versus Cocoa Powder

When researching recipes online, I noticed that the majority of chocolate chess pie recipes used cocoa powder. To me, that makes the most sense given chess pie’s historical context—folks made chess pies out of common pantry ingredients, and cocoa powder is the sort of thing that lasts in people’s pantries forever and ever. It’s the perfect candidate to throw into a chess pie.

But when taste testing chocolate chess pies made with melted chocolate versus cocoa powder, I found that I just liked the flavor of the pies with melted chocolate a lot more. They were more similar to the brownie flavor and texture I envisioned for my pie. But that being said, my favorite brownie recipe actually uses both melted chocolate AND cocoa powder. In general, cocoa powder can add a really intense chocolate flavor (yes, even more intense than melted chocolate, because it’s basically just concentrated cocoa) to baked goods; it can also add a bit of chewiness in brownies. So I decided to use both in my chocolate chess pie recipe too and see what happened.

Spoiler alert: it was delicious! I used natural unsweetened cocoa powder, which gave the chocolate chess pie a slight acidity that’s traditional in old-fashioned chess pie recipes. Note that there are two types of cocoa powders often used in baking: natural unsweetened cocoa powder, and Dutch-processed (also known as “Dutched” or alkalized) cocoa powder. The latter has been treated with alkaline to result in a cocoa powder that’s darker in color, more neutral in flavor, and more chocolatey. Although I usually love using it in baked goods for those reasons, I wanted my chocolate chess pie to have that slight acidity from the natural stuff. Why? Traditional chess pies were often flavored with a dash of vinegar to cut through all the sweetness—I didn’t love the idea of vinegar in my pie, so I thought that natural cocoa powder was a happy compromise. 

Evaporated Milk versus Butter

Most chocolate chess pie recipes also used small cans of evaporated milk to make the filling. I really, really, really wanted to make it work—but when I tried those fillings, the flavor profile of the pie was more “milk” than “chocolate”. When comparing a chocolate chess pie made with evaporated milk and cocoa powder to one made with butter and melted chocolate, there was no competition. It was like comparing a glass of chocolate milk to a fudge brownie. Both good, but the latter was infinitely more chocolatey than the former.

So for my recipe, I skip the evaporated milk completely and just use melted chocolate, cocoa powder, and melted butter to make up the majority of my filling. I love it because it definitely loves up to my goal of having my chocolate chess pie taste like a brownie. But if you’re looking for a more traditional and old-fashioned chocolate chess pie recipe, I suggest finding one that lists evaporated milk as one of its ingredients!

How Do You Make A Chocolate Chess Pie?

There are five main steps to making a chocolate chess pie:

1. Make the Pie Dough
2. Shape into the Pie Crust and Pre Bake 
3. Make the Chocolate Chess Pie Filling
4. Fill the Pre Baked Pie Crust with the Chocolate Chess Pie Filling
5. Bake Again!

Making the chocolate chess pie filling is the easiest part about this recipe. In fact, the most difficult thing about this entire recipe is making the pie dough from scratch and pre baking it. Be sure to check out the next section with all my best pre baking pie tips! 

Questions about Pre Baking Pie Crust

Pre Bake versus Par Bake

First off, let’s get some terminology straight. When I was doing research for the pie chapter of my cookbook, Weeknight Baking, I got really confused because I kept seeing a ton of recipes that either instructed me to “pre bake” or “par bake” my pie crust. I wasn’t sure what the difference was between the two, but it turns out they mean the same thing! Pre baking (or par baking) a pie crust is when you bake the unfilled crust for a short amount of time; after baking, you then fill the pie with the filling of your choice and either bake again to cook the filling or serve immediately if the filling is already done. 

When should you pre bake pie crust?

When a recipe instructs you to pre bake a pie crust, that usually means that the pie’s crust and filling have different baking times. One will need to bake for longer in the oven to be considered done (typically, it’s the crust takes longer to cook than the filling). This is often the case for pie recipes with custard fillings, like pumpkin pie or this chocolate chess pie. Pre baking the crust for those types of pies will give the pie crust a head start by partially baking it; by the time you add the filling to the partially baked crust, both the crust and the filling will be done all at the same time.

Sometimes, the pie crust will need to be completely baked and then filled. This is common for pie recipes like ice cream or pudding pies, where the filling doesn’t need to be baked at all. 

How to pre bake pie crust?

To pre bake pie crust, follow the recipe’s instructions to make the pie dough and mold it onto the pie plate to form the bottom crust. Some recipes will instruct you to bake it right away, but after this step, I always like to freeze the crust since I find that doing so helps keep its shape in the oven.

Once the pie crust is frozen solid, cover the crust with a sheet of aluminum foil. Make sure that its crimp is completely covered. Pour pie weights over the aluminum foil. The pie weights hold the dough in place; without them, the crust has a tendency to puff up in the center and slump down the sides of the pan. You can buy different types of pie weights online or any specialty baking store. However, know that not all pie weights are made equal—the heavier they are, the better. I personally think that the weight chains aren’t as effective as the ceramic beans. 

Alternatively, if you don’t want to buy a specialty tool, you can use other items in your household and pantry. You can use uncooked rice or beans; you can also use spare change in your coin jar. Don’t be afraid to use a lot and fill up the covered pie crust with pie weights all the way up to the bottom of the crimp—a generous filling will also help the pie crust keep its shape in the oven. After you’ve prepped your pie, follow the instructions to pre bake the pie in the recipe.

How long to pre bake pie crust?

Some recipes instruct you to pre bake the pie at a higher temperature for a shorter amount of time; however, I’ve found that doing so has a tendency to shrink my pie crusts. So instead, I always bake my pies at a lower temperature for a longer amount of time. 

How long to pre bake store bought pie crust?

If you follow me on Instagram Stories, you already know that I developed this chocolate chess pie recipe with the help of some store bought pie crusts. Despite being a professional baking blogger, I am not actually opposed to store bought pie crusts—although I personally don’t love the way they taste, I know that they can save you a ton of time and effort (and, as you know from my cookbook, I am all about that lol) in the kitchen. So if you want to skip my pie dough recipe and use store bought one, go right ahead! The pie is still plenty tasty. 

Most store bought pie crusts already come molded onto a disposable pie plate, with instructions on how to pre bake the crust. For my first few tests, I followed the instructions given by the store bought crust but found that the crusts were never crispy or done enough. AI switched back to my tried and tested method of pre baking pie crust (as described in the recipe below) and found it worked much better. 

Questions About My Chocolate Chess Pie Recipe

Can I use store bought crust?

Yes! I mentioned before that when developing this recipe, I tested with store-bought pie crusts. Feel to to use any kind of store-bought pie crust you like (both the kind you roll out and the kind that already come molded onto a pie plate work well here) and follow the recipe’s instructions below to pre bake the store bought crust. 

Do you refrigerate chocolate chess pie?

Chess pie can store at room temperature for an extended amount of time. I like to store my chess pie for up to 48 hours at room temperature, underneath a cake dome (or a large bowl turned upside down over the pie), and then move it to the refrigerator. Before refrigerating, cover loosely with a sheet of plastic wrap.

How long will chocolate chess pie keep?

For about one week: 2 days at room temperature, then another 5 days in the fridge. But note that this pie is best within the first two days of making it; although the flavors develop and intensify the longer it sits, the chocolate meringue top starts to lose its crunchy texture.

What do I serve with chocolate chess pie?

Chocolate chess pie can be kind of intense on its own; I would serve with a dollop of unsweetened freshly whipped cream or some fresh berries on the side. 

Chocolate Chess Pie: Make it Weeknight Baking

In general, I dislike pre baking pie since it can be a time consuming process to bake the pie twice. There’s a lot of sitting around and waiting, especially since you’ll also need to chill the pie dough after making it and before molding it onto the pie plate. If you don’t want to take all day making this chocolate chess pie recipe, I suggest splitting the work up over a few days:

1. Day One: Make the Pie Dough, Form the Bottom Crust, and Freeze Overnight!
   (around 30 minutes of Work Time, plus 1 hour of chilling)
   
   
2. Day Two: Pre Bake the Frozen Pie, Make the Filling, and Bake the Pie Again!
   (around 5 minutes of Work Time, plus 1 hour and 20 minutes of Bake Time)

If that still seems like too much time in the kitchen for one project, you can break it down even further:

1. Day One: Make the Pie Dough and Refrigerate Overnight
   (around 15 minutes of Work Time)
   
   
2. Day Two: Roll Out the Chilled Dough, Form The Bottom Crust, and Freeze Overnight
   (around 15 minutes of Work Time)
   
   
3. Day Three: Prebake the Pie, Make the Filling, and Bake the Pie Again
   (around 5 minutes of Work Time and 1 hour and 20 minutes of Bake Time)

I know it seems excessive to break up the recipe over two or three days, but if you look at the schedules closely, you’ll notice that it dramatically decreases the time you spend in the kitchen actively working. You’re free to go on and do other things as the pie dough chills or freezes overnight! I call this kind of recipe planning “making the recipe fit into your schedule”. If you like this kind of time management, be sure to check out my cookbook, Weeknight Baking, where I break down all sorts of baking recipes in this way.

More Chess Pie (or Similar!) Recipes

• Funfetti Buttermilk Chess Pie
• Matcha Buttermilk Chess Pie
• Meyer Lemon Chess Pie
• Momofuku Milk Bar Pie (for High Altitude!)
• Salty Honey Pie

Chocolate Chess Pie Recipe

yield: 1 (9-inch) pie

Prep Time: 10 mins

Work Time: 1 hr 5 mins

Bake Time: 50 mins

5 from 1 vote

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Ingredients

For the Stand Mixer All-Butter Pie Dough

• 3 Tablespoons (1.5 ounces or 43 grams) very cold water
• 1 ½ teaspoons apple cider vinegar
• ½ cup ice
• ½ cup (4 ounces or 113 grams) very cold unsalted butter
• 1 ¼ cups (5.65 ounces or 160 grams) all-purpose flour
• 1 ½ teaspoons granulated sugar
• ½ teaspoon kosher salt

For the Egg Wash:

• 1 large egg
• 1 teaspoon water
• pinch of kosher salt

For the Chocolate Chess Pie Filling:

• ¾ cup (6 ounces or 170 grams) unsalted butter, chopped into 1- to 2-inch pieces
• 3 ounces (or 85 grams) dark chocolate (between 60 to 70% cacao), chopped into 1- to 2-inch pieces
• 1 ½ cups (10.5 ounces or 298 grams) granulated sugar
• 3 large eggs
• 2 Tablespoons natural unsweetened cocoa powder
• 1 teaspoon pure vanilla extract
• ½ teaspoon kosher salt

Instructions

For the Chocolate Chess Pie:

• First, make the pie dough: In a large liquid measuring cup, whisk together the water and vinegar. Add the ice and whisk, Refrigerate while you prep the rest of the ingredients.
• Cut the butter into 1-inch cubes and place them in a small bowl. Freeze while you prep the rest of the ingredients.
• In the bowl of a stand mixer fitted with the paddle attachment, combine the flour, sugar, and salt. Beat on low until just combined, about 15 seconds. Add the butter all at once and beat on low until the mixture has the texture of coarse meal, with pea-sized pieces of butter throughout, about 3 minutes.
• Remove the ice water mixture from the refrigerator. With the mixer on low, add 4 tablespoons of liquid from the ice water mixture. Beat on low for 2 to 3 minutes, or until the dough clumps around the paddle and/or sides of the bowl. If the dough seems too dry, add more liquid from the ice water mixture 1 teaspoon at a time.
• Tip the dough out onto a lightly floured counter with the spatula. Quickly knead the dough into a rough ball. Wrap the dough tightly in plastic wrap and flatten into a small disc. Refrigerate for at least 1 hour.
• Now, form the bottom crust: Roll out the disc of chilled dough on a lightly floured counter and fit it onto a 9-inch pie pan. Crimp the edge and use a fork to poke holes all over the bottom and sides of the dough. Cover loosely with plastic wrap and freeze overnight.
• Prebake the crust: Position a rack in the center of the oven and preheat the oven to 350°F. Line a sheet pan with parchment paper and place the frozen crust, still in its plate, in the center of the pan. Cover the crust with foil, making sure the crimped edges are completely covered and that there are no gaps between the foil and the crust. Fill with pie weights and spread them out so they are more concentrated around the edges of the crust.
• Bake for 35 minutes. While the crust is in the oven, make the egg wash: In a small bowl, whisk together the egg, water, and salt.
• Remove the sheet pan from the oven, keeping the oven on. Carefully lift out the pie weights and foil. Use a pastry brush to coat the bottom and sides of the pie crust (but not the crimped border) with a thin layer of egg wash. Bake, uncovered, for an additional 5 minutes. Set aside on a wire rack to cool slightly while you make the chocolate chess pie filling.
• Now, make the chocolate chess pie filling: Place the butter and dark chocolate in the top pan of a double boiler or in a heatproof bowl set over a heavy-bottomed sauce pan filled with a few inches of simmering water (be sure the bottom of the bowl does not touch the water). Cook over medium heat, using a heatproof rubber spatula to stir the mixture and scrape the sides of the bowl occasionally, until the butter and chocolate have melted and combined, about 10 minutes. Set the double boiler or bowl on a wire rack and let the chocolate mixture cool while you prep the other ingredients.
• In a medium bowl, whisk together the sugar, eggs, cocoa powder, vanilla, and salt. Slowly add the chocolate mixture and whisk to combine. Pour the mixture into the pie shell.
• Bake for 50 to 55 minutes, or until the edges are set and the center of the pie just slightly jiggles. Cool on a wire rack. Serve slightly warm or at room temperature. The pie can be kept at room temperature, under a cake dome or a large bowl turned upside down, for up to 3 days.

NO TIME TO BAKE?!

Over the past several years of running Hummingbird High, I kept a crucial aspect of my life hidden from my readers: I had a full-time, extremely demanding job in the tech world. In my debut cookbook, Weeknight Baking, I finally reveal the secrets to baking delicious desserts on a tight schedule.

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